The Dreamer: How Developer Tom Gilmore’s Wild Idea Launched the Downtown Loft Craze

The trend is giving the area new life. But will he be left behind?

For their senior project on downtown Los Angeles, the Buckley School’s class of 2004 have been treated to a taste of life after graduation as they would like it to be. Just yesterday, the 58 students of the elite San Fernando Valley academy descended on the city’s historic core. They strolled through streets of once-dead office buildings—lovingly restored and remade into the most compelling urban neighborhood L.A. has spawned since the late 1800s. Today they’ve returned to Buckley’s 19-acre campus in Sherman Oaks, where they have spent the morning being lectured to by a mayoral aide, an architect, and a researcher of the homeless. No wonder, then, that more than a few of the teenagers have made pillows of their outstretched arms.

The students perk up slightly as their teacher talks about Senior night at Disneyland. Like Buckley, she informs them, the theme park will be imposing a dress code.

“Damn!” whispers Tom Gilmore, lingering in the back of the room. “And I was going to wear my thong underwear.”

Gilmore is not the Buckley class clown. He’s a real estate developer and the afternoon’s speaker. The sidewalk cafes the seniors saw, the galleries, the young couples pushing baby strollers or walking dogs—Gilmore made this wild, defiant, exuberant landscape possible, by virtue of his own wildness, his own defiance, his own exuberance. Four years ago, with no money and no track record, he turned his attention to the not miserable intersection of downtown—4th Street and Main. There he bought four abandoned historic buildings; the Hellman, the San Fernando, the Continental, and Farmers & Merchants Bank. Gilmore’s dream was not just to salvage some real estate but to create a whole neighborhood he christened “the Old Bank District.”

By August 2000, eight months after his purchase, Gilmore had transformed the San Fernando into lofts and leased them to near capacity. Far from falling on his face, as many had predicted, Gilmore proved that he could attract young pioneers who would pay rents as high as those in Silver Lake or West Hollywood to live in a block-long neighborhood hemmed in by prostitutes and drug addicts, homeless missions and transient hotels.

Gilmore was not the only catalyst for downtown’s revival. The Staples Center and, more recently, Disney Hall have pulled in thousands of new visitors. In the ’90s, the state of California corralled the bulk of its local employees into the Ronald Reagan State Office Building on Spring Street and a retooled 1914 department store on Broadway. In 1999, a year before Gilmore embarked on the Old Bank District, the city passed its adaptive reuse ordinance, which for the first time made converting a historic office building into housing cheaper than tearing it down and throwing up a new one in its place. Soaring rents, low interest rates, increased demand—all contributed to today’s climate. But Gilmore, by reclaiming an entire block, can justly take credit for launching what will surely be L.A.’s last great residential boom—a five-minute stroll from City Hall.

If Gilmore could recast one of the most decrepit, hopeless stretches of downtown into an urban paradise, imagine the opportunities for more seasoned players. Now, after Gilmore planted his flag at 4th and Main, real estate companies with hundreds of millions at their disposal are converting offices, hotels, warehouses, and garment sweatshops into lofts. As of April, 15,300 lofts have gone on the market; another 8,800 are under construction. Buildings that lay fallow for decades are attracting bidders al $50 per square foot—six times what they would have commanded before Gilmore.

For these developers—indeed for the city of Los Angeles—Gilmore’s gambit has created enormous value. However, Gilmore himself is millions in debt, has lost deals and partners, sometimes bitterly, and has been forced to sell off portions of his empire. Through it all he has remained a master salesman whose finest products are his ideas and whose greatest gift is his ability to sell himself.

Take a hard look at his business or pore over court records or talk to former colleagues, and you’ll find numerous contradictions. Gilmore is a venture capitalist with no venture capital, a child of destiny and a supremely late bloomer, a self-proclaimed socialist who has opposed the living wage, a lazy man trapped in a busy man’s body. He’s equal parts compassion and vengeance. He’s a visionary who can be narrowly petty.

Even so, none of his adversaries can entice you or appeal to your higher nature as Gilmore does—a fact all of them should understand, for they, a month or a year or a decade ago, were seduced themselves. Whenever Gilmore looks out on a crowd, whether it’s businessmen at a Biltmore breakfast or a class of high school students, it is always the same. He’s embarrassed that you’ve singled him out for such an honorable distinction, always asking your forbearance, always amazed that you would take time out of your undoubtedly busy day to listen to the likes of him. Why is he even up here? He should be seated, listening in rapt attention to you. It’s all shtick, of course, exceedingly charming shtick, but that doesn’t mean Gilmore doesn’t believe it.

With ambling strides, Gilmore reaches the front of the class. He perches himself on a desk, beneath multicolor placards touting HONESTY, LOYALTY, RESPECT, KINDNESS, and SELF-DISCIPLINE. The tweedy suit he bought al the Hollywood Suit Outlet fits him in an off-the-rack kind of way, and he’s wearing it like a concession—much as one of these students might dress for Senior Night at Disneyland.

Six feet four, Gilmore has rosy cheeks and is still as boyishly handsome as one can hope to be at 51. He turns his gaze on the assembled Buckley students, and as they clap, he responds with a broad, crooked, eternally grateful smile. “I love talking to high school students,” he begins, “but I’ve never actually done it since I was in high school. I do talk to a lot of different people. But it is really different talking to you, because in an oddball way, the way I approached downtown when I first got there was a lot more like a high school student than some kind of big fat businessman trying to figure out a business deal.”

Gilmore tells them how he first came to L.A. in 1988, settled into a house in Manhattan Beach, and soon enough began pestering a few friends. Where were they going to hang out? He’d lived in New York City, and he was used to hanging out in an urban environment.

His friends took him to a bar in Beverly Hills. “This really isn’t a city,” he told them. “This is like a little town.” Two days later they took him to Century City. “A couple of big buildings, there’s a plaza. It’s very nice, but this is not a city.” Santa Monica was next. “Good try. Show me the city, the place where it’s really going on in the middle of your town,” he remembers saying. “They went, ‘Oh, oh, oh! You mean like downtown?’ I said, ‘Yeah, downtown,’ and they looked al me like I was crazy. They were like, ‘Well, nobody goes downtown. Nobody in L.A. even knows where downtown is.’” They drove him to Bunker Hill’s phalanx of skyscrapers. Gilmore arrived at six at night, and the towers were there but no people. He asked them what kind of city was this anyway, that rolls down all the gates and goes to sleep when the sun goes down. “And they were like, ‘Hey, man, that’s just the way L.A. is. L.A., it’s a suburban place. “We don’t do city stuff here.’”

The heads are off the desks. “Everything I knew about cities, I knew, like, as a high school student,” says Gilmore, who grew up on Long Island, as removed from the center of things as these kids are. “I was like, ‘That’s where stuff happens.’ That’s where we hung out on the streets. That’s where we met in the clubs. So I couldn’’t understand how people could—I was like, ‘You mean to tell me everything that everybody does in this town when they’re 16, 17, and 18 years old, they’ve got to get into a car?’”

In just a few moments, Buckley students will tail Gilmore out the classroom, hitting him up for internships, asking him if he has any lofts available for incoming USC freshmen. First, though, he delivers a few parting words of caution that are not words of caution at all. “Something terrible happens to you when you leave high school,” he says. “People want you to fit within a format that they understand. Let me tell you now in advance, because you’re all graduating now: There is no reason to try to fit into anybody else’s format. The brain you have is no more inferior to my brain than my brain is to a 70-year-old’s. You are already cooking on all your cylinders. What seems absurd to you is absurd. What seems rational to you is rational. Don’t let people tell you what needs to be, what the city of Los Angeles is, what it must be, and how you need to fit into it. None of that is true. Los Angeles is very much like a teenager itself.”

If L.A. is indeed a teenager, then has been the badge of its perennial immaturity. It is the source for so many damning cliches—Los Angeles is a hundred suburbs in search of a city, the big nowhere, the freeway metropolis. Certainly all the attempts to improve downtown—from the office towers of Bunker Hill to the concrete tomb of the Dorothy Chandler Pavilion—have only provided embarrassing material for Woody Allen movies. To see the vital center—the pulsing commercial, political, financial, and retail heart that was once L.A.’s downtown—you’d have to go back 60 or 70 years. On Broadway you’d see a row of movie palaces, theaters, and department stores. On Spring Street, the “Wall Street of the West,” you’d see stock traders, real estate barons, and transportation magnates brushing shoulders. On the top floors of office buildings—like the Charles Frost and the Walter P. Story—that so proudly bore their names, you could glimpse self-made men who’d amassed their fortunes from land or oil and built these monuments where every ornate banister or stained-glass skylight was a testament to their wealth and permanence. You’d see commuters by the thousands pouring out of the Pacific Electric and Subway Terminal buildings.

If you wanted to see L.A.’s downtown the day it established itself, you could do worse than March 25, 1905, when the city witnessed perhaps the greatest rolling procession of wealth in its history. Three teams of horses strained down Main Street, hauling behind them $2 million in gold coin sealed in steel strongboxes. The deposits of Farmers & Merchants Bank were bound for their new home, a splendid Grecian temple at 4th and Main.

Just back from a two-month European vacation, the bank’s founder, Isaias W. Hellman, presided over the festivities. An emigre from Bavaria, he opened Farmers & Merchants in 1871; it became the region’s first great indigenous bank, and Hellman emerged as the city’s leading financier. In late 1876, a decade before American Israelite Magazine would name him “the richest Jew in America,” Hellman finished his Victorian mansion at 4th and Main—the most desirable residential location in Los Angeles.

In 1903, as L.A.’s business center spread south, Farmers & Merchants bought the land under its founder’s mansion to build its new bank. The Hellman home now began a journey that would signal the end of the settled residential life at this stretch of Main Street for the next 95 years. First, it was hauled off to 18th Street and Figueroa. When downtown again lapped against it, the mansion drifted to West Adams, whereupon it vanished.

It took six years to complete the new bank district. The Continental, once the city’s tallest skyscraper, was constructed in 1904, as was Henry Huntington’s Pacific Electric Building. The San Fernando, financed by Colonel J.B. Lankershim, opened in 1906. Hellman’s office building, which bordered his bank on two sides, went up in 1909.

The bank district’s decline was just as swift. By World War I, the Owens Valley Aqueduct had precipitated suburban flight on a vastly expanded scale. The proliferation of the Ford Model T made downtown nearly unnavigable and speeded the demise of the streetcar system. Bullocks Wilshire and the May Co. on Fairfax eclipsed Broadway’s department stores; downtown’s movie palaces hemorrhaged customers under new competition from Hollywood and Westwood. After World War II, cheap G.I. home loans and the freeway system delivered the coup de grace.

By the end of 1945, Farmers & Merchants held deposits of $304 million. But it would profit from the postwar boom not at all. In 1956, citing its “lack of branches”—a liability in a city as spread out as L.A.—and the “difficulty of holding and securing desirable business in present location,” Farmers & Merchants was absorbed into the Security-First National Bank. The Grecian temple that Isaias Hellman built would remain open for a while longer as a Security branch. The city, tenant of last resort, took over the San Fernando and the Hellman for its transportation and housing bureaus. Then the city, too, abandoned 4th and Main. Along with Farmers & Merchants, the district was dead.

In December 1997, 41 years after Farmers & Merchants capitulated, drugs, panhandling, and prostitution were the dominant forms of commerce at 4th and Main. The entrances to the Continental, San Fernando, and Hellman were welded shut, their ground-floor windows plugged with plywood and steel. But it was the bank’s degraded state that most resonated with Gilmore. “It sort of looked like a fallen king,” he says. “No longer in its prime, it was every bit as beautiful and noble as it ever was, but the world had fallen down around it.” Gilmore was 44 at the time, and his prospects seemed about as sound as 4th and Main’s.

The son of a machinist, Gilmore was raised in the “lowest middle class.” His older brother, Ray, would become a cop and a restaurateur. His younger brother, George, would find some fame as a rockabilly singer and a fixture in New York’s East Village. Gilmore, though, always saw himself fulfilling a higher purpose. “Tom was sort of working on his legacy from when he was ten years old,” Ray says. “Most of us learn how to spell legacy when we’re 20.”

Out of community college, Gilmore drifted as a dishwasher and a Middle-distance trucker. For several years he subsisted as a gardener on a Connecticut estate, an experience, he says, that was “the closest I’ve ever come to slavery in my life.” A few of his neighbors in Connecticut had heard that Gilmore designed gardens and wondered if he could do theirs. “I’d lie and say, ‘Of course I design gardens’” he recalls, “and slowly but surely began to develop a business.” He took classes in urban landscape architecture at the City College of New York, where he discovered a novel way of avoiding the five-year curriculum of school and the three-year apprenticeship required to obtain a license. “I knew a licensed architect in Connecticut without a client to his name,” Gilmore says, “and I was a kid with a lot of clients and not a license to my name.” So he left school and established Gilmore Design in 1984; an early project was conceiving a restaurant for his brother Ray at Manhattan’s South Street Seaport. Gilmore’s idea—a floating seafood restaurant built out of two shipping containers welded together—showed flair.

He won some more restaurant commissions and moved into Manhattan. He became a regular at Elaine’s, the Upper East Side hangout where George Plimpton, Walter Cronkite, Liza Minnelli, and future LAPD police chief William Bratton, among others, would mingle. There he met the actor Dabney Coleman, who remains his best friend. In Elaine’s meritocracy of inspired gab and tall tales, Gilmore rose to a level the world had denied him. Manhattan, if it noticed Gilmore at all, would damn him as a twopenny dreamer. But at Elaine’s, the city’s achievers—its novelists, politicians, journalist, filmmakers—would light up when Gilmore made his entrance.

By 1988, Gilmore recalls, his annual income had reached $90,000—less than Liza or Dabney might make in a week, but more money than he’d ever earned. Two years later, it nose-dived to $15,000, a catastrophe he blames on the economy. He couldn’t even spare cash for his own drink, let alone a round, and still he couldn’t not show up at Elaine’s on a Thursday or Friday night. If you weren’t there, the crowd would think there was something wrong, and that was a conclusion that Gilmore couldn’t allow them to reach.

“During the downtime,” he remembers, “when I was really hurting—I should never say this, but I would go to Elaine’s dressed in a suit and tie, as always, doing the whole thing. When the world was falling apart, there were people there who were going to be my clients. I couldn’t come in hanging my head down.”

Soon enough, Gilmore did what generations of beaten-down New York dreamers have done: He fled to Los Angeles. He flew out to design the Tribeca bar and restaurant in Beverly Hills for a partner of his brother’s, then built a few more Tribecas in Encino and San Diego. His earnings were abysmal. “The dollars were getting smaller and smaller,” he says, “but the weather was getting warmer and warmer. Then I got lucky.”

Jerri Perrone, another of Ray’s friends, was an executive with a New York investment firm called Sentinel, which owned the International Jewelry Center in downtown Los Angeles. She hired Gilmore to supervise the partitioning and build-out of the center’s last raw floors. He was relieved to be billing his usual architectural fee for 60 days straight. Afterward, he was hired as the center’s property manager. He fell in love with the tenants—deal makers mostly from Asia and the Middle East. “It was the greatest all-star team of negotiators in the world,” Gilmore says, “and there I was, this shanty Irish New York goober.” He also fell in love with Trish Keefer, a former model and James Bond girl who worked with him. Three weeks after they went to Istanbul on a lark, he proposed marriage—his third.

In 1995, when the Jewelry Center went up for sale, Gilmore decided to buy it. The price was more than $20 million, and he had about $1,000 in the bank. His play for the building was no more unlikely than his launching a landscape design business without ever having designed a landscape or founding an architecture firm without the benefit of a license. But whether it was middle age or intoxication with Los Angeles, Gilmore had raised his game.

Gilmore says he told Sentinel about his intentions. “I don’t think they thought I had a rat’s chance in hell. It was like a kid saying, ‘I want to go to the moon.’” But, he says, the company told him to go for it.

He did find an investor Judah Hertz was a developer recently arrived in Beverly Hills, who had substantial holdings in New York and Florida. The idea was for Sentinel to sell the building to him for $25 million; he’d pay Gilmore $500,000 to $1 million as a finder’s fee. “At the ninth or tenth hour in the process,” Gilmore says, “Sentinel balked about me being in the deal. And to this day, I don’t know why.” Perhaps, he says, the company’s local reps, who’d told him he could knock himself out, hadn’t informed the bigwigs back East. Not long after the Sentinel executives noticed his name on the contract, Gilmore, under armed guard, was escorted out of the building. (Sentinel would not comment on its experience with Gilmore.)

Hertz bought the Jewelry Center anyway. While he didn’t give Gilmore a piece, he hired him as his company president. “He cut me loose,” Gilmore says, “to create a new vision for his company.” Hertz says he brought in Gilmore out of pity. “He was like, ‘I’m going to be homeless. I have no job, no nothing.’ I gave Gilmore a job because I felt so bad for the guy.”

Gilmore made the most of his newfound status, speaking at downtown business luncheons, delivering bold declarations to reporters as the company acquired landmark properties like the Oviatt Building and the Park Plaza Hotel. “Judah and I would put the deal together,” says Wolfgang Kupka, Hertz’s real estate broker at Cushman & Wakefield during this time, “and Tom took all the credit for it.”

“Judah was getting the best of both worlds,” Gilmore says. “The press was all favorable. All the publicity was giving the Hertz Group a credibility that I don’t believe it had prior to that, but at the same time, it was my neck on the line.”

“The only one who had no credibility at the time was him,” Hertz says. “He’d go all over the city getting publicity I didn’t want. I’d meet someone, and they’d say, ‘Oh, you work for Gilmore.’”

As Gilmore tells it, his estrangement from Hertz stemmed from his growing sense of mission, his sense that he might just turn the tide in L.A.’s beleaguered downtown—a grand philosophical endeavor much larger than Gilmore himself, and certainly more significant than Hertz. The city that had long snubbed and shirked its center was about to discover it anew. Like other prophets, Gilmore had nothing to offer but his zeal.

“I was like, ‘Holy shit!’” he says. “It’s like the first time you look at a volcano. ‘Oh, my God! That’s where it is!’ I was no longer focused on how I fit. All of a sudden, it wasn’t really about me anymore. It was about it. That didn’t happen until I was 40 years old. And no, I wasn’t going to forget me. I wasn’t going to sublimate my ego by any stretch, but the bigger stuff had become more important to me than ‘How am I going to make a dollar next week?’ I think that I assumed that, while important to me, money was going to be secondary.”

It—this karmic vision of a city finally finding its essence, with Gilmore as its champion—pried him apart from Hertz.

“I was deciding he was too shallow,” Gilmore says, “and he was deciding I was too deep.” According to Gilmore, Hertz told him he was crazy to pursue the Old Bank District but then proceeded to buy a half share in the Continental for about a quarter of a million dollars.

Ray Gilmore knows what he would do if he saw Hertz on the street. “If I ran into him today—and Tom would kill me—I’d shake his hand for what he did for my brother George.” George Gilmore had no health insurance when he was diagnosed with a severe heart ailment in 1998. A major fund-raiser for UCLA Medical School, Hertz arranged to have a leading heart specialist perform emergency surgery. “From the benefit of 3,000 miles away,” Ray says, “what Judah did for Tom was gigantic, but what he did for my brother George was off the charts.”

It is a topic Hertz himself isn’t above broaching. “By the way, did he ever mention his younger brother?” Hertz asks, when interviewed at his offices. “Ask him how his brother’s doing. I gave him his whole start and everything, and he’s mad at me?”

One Monday in 1998, Gilmore says, he left the Hertz Group’s headquarters, crossed the street, and rented a tiny room of his own. “I had that great moment of walking out of the office, saying, ‘What have I done? Oh, shit.’ Within weeks he bought the Clifton’s Silver Spoon Cafeteria building on 7th Street for $220,000.

Hertz offers another account of Gilmore’s departure. “I basically fired him,” he says. “Not basically—that’s what I did. The whole office could hear him screaming from a mile away.” Asked about his boss’s version, Gilmore confirms it. “If you really look at it, you could say he fired me,” he says, laughing, “if you can say you fired someone after he tells you to go fuck yourself.”

“If I have a disagreement with someone or had a falling-out,” Ray Gilmore says, “you can bet within a week or two weeks or a month, I’ll have patched the fence. When someone does Tom—not necessarily a perceived wrong, it has to be a lot stronger than a perceived wrong, but something he really feels is a wrong—they just become dead to him. They just don’t exist.”

One lunch hour, Gilmore strolls 4th and Main with the confidence of a man whose worst ordeals are behind him and whose best prospects he ahead. Which is to say, Gilmore has put on his public face.

Through cheap sunglasses he surveys the resplendent facades of his Hellman and San Fernando buildings. On the ground floor, small businesses are beginning to crop up. The Bank gallery displays an installation of stuffed animals engaged in a staring contest; the Situation Normal boutique flaunts edgy Japanese and European designers with names like Hectic and Surface to Air. Yoga Circle Downtown doesn’t charge pupils but takes only contributions. The lofts themselves come finished (the San Fernando) of raw (the Hellman) and range from a 565-square-foot studio to a 2,400-square-foot penthouse.

Among the residents are transplanted New Yorkers and Chicagoans starved for a taste of grit, former L.A. suburbanites bored by the malls and the multiplexes, junior entertainment executives reverse-commuting to Burbank, working artists and those who fancy themselves artists, USC and Southern California Institute of Architecture students, first-time renters and empty-nesters, and of course the dogs. “One hundred and ten dogs,” Gilmore says, “but we’re counting the Chihuahuas.” Not since Walt Disney opened the Magic Kingdom has a Southern California attraction so religiously reflected the optimism of its creator.

Gilmore greets his tenants more with the gusto of a ward boss they unanimously voted for than with the formality of a landlord who collects the rent. Gilmore and his wife live in a modest house in the Hollywood Hills. If it were up to him, he says, he would live in the Old Bank District, but his wife—who is the district’s general manager—insists that they have some refuge. He stoops to the gutter to pick up a supermarket circular and slips it into a garbage can. On 4th and Main, Gilmore is mayor and constable, tree trimmer and trash collector, power broker, occasional emergency medical technician, and director of public relations. On this block and this block alone, it—Gilmore’s karmic vision—is in full bloom.

He crosses Main toward Pete’s Cafe and Bar, the San Fernando’s corner restaurant, which he co-owns. Mayor James Hahn comes here to eat every few weeks or so, and Kiefer Sutherland sometimes stops by for a drink. Gilmore prefers to sir on the curbside patio, where he’s immediately hit up by a panhandler with ragged clothes and a matted beard.

“Champagne wishes and caviar dreams,” the panhandler says.

“How are you doing, man?” asks Gilmore, flashing a smile that is more like a grimace.

“Lifestyles of the rich and famous.”

“Good to see you, man.”

“Could you help a brother out?”

“Not at the restaurant, man. I appreciate it,” Gilmore says. “Thanks, man. Thanks, man.” He hurries the panhandler on his way and puts in his order for a veggie quesadilla (he’s been a vegetarian for three decades). He notices another visitor coming his way. “Hold on,” he says, rising to shake the hand of the Speaker of the California State Assembly. “This is Fabian Núñez. You know Fabian?”

“I’m glad we ran into each other,” Núñez says.

“How are you, sir?” Gilmore asks. “Come sit down.”

Núñez is happy to offer a Gilmore critique. “Tom’s more than a visionary,” he says, “because a visionary just envisions. Right! This is a man who takes matters into his own hands.”

“I’m a street urchin,” Gilmore says.

“He’s a hands-on practitionary,” Núñez says. “That’s what it is, not a visionary—a practitionary.”

“Now,” says Gilmore, “if I could only get this state to come across once in a while!”

In January 2000, Gilmore would have been hard-pressed to qualify for a loan on a luxury car. Still, if he had been waiting his entire life for an opportunity like 4th and Main, maybe 4th and Main had been waiting all that while for a Tom Gilmore. Like him, this tattered intersection was ready to shuck its squalor and mediocrity and past disappointments and hurl itself into a new and vital life.

When Farmers & Merchants built its headquarters at the heart of the Old Bank District in 1905, it had cost about $12.7 million in today’s dollars. Ninety-five years later, Gilmore bought it for about $100,000, less than 1 percent of its original value, less than a two-bedroom Studio City condo at the time. The eight-story San Fernando cost him $1.8 million, the price of a four-bedroom house in Pacific Palisades, while the Hellman, which is really two six-story buildings and one seven-story building joined at the hip, went for under $4 million.

Not that Gilmore could afford these properties, however ridiculously cheap. The federal government and the City of Los Angeles had money available, and Gilmore took on a couple of partners to get it. He lured Jerri Perrone, the former Sentinel executive and friend of Ray’s, to come to L.A. Perrone used her expertise in accounting and tax law to structure a $25.7 million loan backed by the U.S. Department of Housing and Urban Development—$6.5 million of which went to buy the buildings and $16.4 million to convert them.

Charles Loveman, the other partner in Gilmore’s original triumvirate, cast his lot with the Old Bank District after abandoning a downtown reuse project of his own. “I met Tom and was charmed by him, like everybody, right away,” says Loveman. Gilmore put Loveman’s background with the Community Redevelopment Agency to good use. Loveman arranged for the Old Bank District to receive $5.5 million in tax credits. Working with councilwoman Jan Perry, Loveman also put together a package of $5.1 million in L.A. city loans to complete the renovations. Gilmore is required to pay only interest until his project turns a profit. Despite all this public backing, Gilmore still ran out of money three-quarters of the way through the reconstruction. He turned to his wife’s stepfather, whose investment firm extended him $2.5 million to finish it.

Loveman and Perrone may have provided financial and legal expertise, and Gilmore’s stepfather proved crucial, but nothing can diminish Gilmore’s salesmanship—his ability to conflate his own business interests with a civic endeavor in which politicians, preservationists, and the press are grateful to participate. In Los Angeles, where the phlegmatic Richard Riordan passed for a dynamic mayor, and Hahn, his successor, has compared himself to a “glorified janitor,” Gilmore fills a charisma vacuum. Local reporters, bereft of real estate personalities—no Donald Trump here—were willing to advance Gilmore credibility on the strength of grand pronouncements alone.

Carol Schatz of the Central City Association lobbied the city council for nine years before it passed its adaptive reuse ordinance in 1999. During that time, she never received a single call from her downtown business membership expressing interest in converting defunct office buildings into housing. Tom Gilmore ended that long dry spell.

“When I met him, I remember thinking, ‘This guy is incredible,’” Schatz says. “He was young and attractive and articulate and fun.” It amazed her that this freewheeler who had materialized out of nowhere had emerged as the catalyst for a renewed downtown. “You would have thought it would be a Rob Maguire or a Jim Thomas,” she says, referring to the real estate team who built several of the city’s skyscrapers, “or one of these other guys who had been big downtown stakeholders and developers.”

The story of Saint Vibiana’s Cathedral, which the city bought on Gilmore’s behalf in the summer of 2002, is the most exquisite illustration of the developer at work. For his business partner on the cathedral, Gilmore brought in former Los Angeles Times reporter Robert Jones, who in a 1996 column had celebrated the archdiocese’s decision to leave “the scum-covered abandoned-building district of Saint Vibiana’s.” Gilmore courted the reporter, and in October 1999, before he acquired 4th and Main, Jones wrote a cover profile of Gilmore for the Los Angeles Times Magazine; titled “Once More, with Enthusiasm,” it anointed him downtown’s lovable gambler, its greatest optimist—and its best hope.

“That was huge,” Gilmore says. “When it came to getting through government bureaucracies, it turned out that article was actually what made it tumble for us. People were like, ‘Oh, yeah, you’re that guy. Sure, we could get that done.’ It was a real enabling mechanism.”

Jones left the Times a few months after the piece was published. He and Gilmore remained in touch and later that year partnered to buy Saint Vibiana’s. “It just intrigued the hell out of me that we could sort of come in and take a wild chance,” Jones says, “and maybe assure that that building would exist for generations to come. That was exciting to me. It was so different from journalism.”

For Gilmore and Jones’s $200,000 deposit, the archdiocese agreed to give them Saint Vibiana’s for two years, at the end of which they had to come up with the $4.65 million purchase price. At the end of the first year, the city paid Gilmore and Jones $2 million for the cathedral’s 2nd Street frontage to build a new Little Tokyo Library. With the partners unable to come up with the balance, and with the archdiocese rumbling about foreclosure, the City of Los Angeles offered to buy the alley behind the church, with the understanding that Gilmore and Jones would buy it back later with interest and build new housing there. The city’s appraiser priced the alley at $2.75 million, which was immediately forked over to the archdiocese. In 2000, the state legislature passed a bill to grant Gilmore and Jones $4 million to retrofit Saint Vibiana’s as a performance space and auditorium for Cal State L.A.

Gilmore would grab four more buildings by the end of 2000. One of his new properties, the Hollywood Equitable Building at Hollywood and Vine, was beyond downtown’s orbit, but the rest were not. With club owner Cedd Moses, he bought the defunct El Dorado Hotel, adjacent to the Hellman Building. With an affordable housing company called Simpson Housing Solutions, Gilmore bought the Rowan Building, just south of the El Dorado. On Broadway, he bought the faded but still splendid Palace Theater, where he set up his headquarters. He acquired as much and as quickly as he could before his own resounding success at 4th and Main would price him out of the market. Who should benefit from the renaissance more than he, its Dante and its Giotto?

Throughout downtown’s historic core, adaptive reuse projects—better financed than the Old Bank District and several times its size—are attracting tenants and condo buyers. Last year, the KOR Group, which owns seven hotels and 3,700 apartments, constructed 322 lofts at the sprawling former Mobil Oil headquarters at 6th and Flower. This March, CIM Group, the firm that transformed Santa Monica’s 3rd Street Promenade, debuted the Historic Gas Company Lofts, the first phase of a project that win bring in 1,500 new apartments and downtown’s first supermarket. MJW Investments, which was named the fastest-growing private company in L.A. by the Los Angeles Business Journal three years ago, has opened the first phase of Santee Court, nine former garment factory buildings, which contains 578 lofts along with gardens, hot tubs, and a putting green. Even the Subway Terminal and Pacific Electric buildings, the two forsaken hubs of L.A.’s streetcar system, will be reborn as lofts by March.

Gilmore, for his part, has not completed a single unit since he finished the Continental Building in 2001. But you’d never know it the way he barnstorms across downtown. Working ballrooms full of businesspeople, smiling at the jokes of opinion makers, Gilmore has dominated the public stage as masterfully as he once played the bar at Elaine’s.

After the Old Bank District he was tens of millions in debt. His decision to buy tens of millions more worth of property before the market boxed him out plunged him back into the financial chaos he’d endured all his life, but on a far more operatic scale.

“We stretched ourselves to the maximum possible pre-death level you could stretch to,” Gilmore says, “and then held on like barnacles to weather the inevitable storm. It was like, You have bought as much land as a human being could possibly buy without going broke. Hunker down and then wait for the storm. You spend a year or two in what feels like a hurricane.”

Jerri Perrone admires her partner for having raised calamity to the level of a fine art. “With Tom, it’s always ‘No problem,’” says Perrone, whose own father was an entrepreneur who lost the family house a couple of times.

“I think Tom never feels so alive as when someone’s got a pistol to his head, starting to pull the trigger,” says another associate. “Unfortunately, that’s no way to run a business.”

As Gilmore weathered the storm, he unloaded real estate. He sold the Palace Theater in the same unrestored condition in which he had bought it. He sold off the Clifton’s Silver Spoon Cafeteria building, where he once hoped to live, to Cedd Moses. He and Moses sold half their stake in the El Dorado to Goodwin Gaw, a 35-year-old real estate developer who owns the Bradbury Building and the Hollywood Roosevelt Hotel.

In Gaw, Gilmore may have found the ideal business partner. “Tom is right,” Gaw says. “You do have to control an entire block to create a neighborhood.” Which doesn’t mean Gaw is blind to his new partner’s predicaments. “Sometimes I don’t know how he sleeps at night,” he says. “Tom’s just constantly stretched out in every which direction.” Still, Gaw, a successful developer and scion of a Hong Kong real estate family, confesses an admiration for Gilmore’s swashbuckling. “I think part of me would like to be like him sometimes,” Gaw says, “where you can go do things without having to think about financial discipline.”

Of all his undeveloped projects, Gilmore’s Rowan Building project began the most auspiciously. By the summer of 2001, he had his $27.5 million of Los Angeles Community Redevelopment Agency bonds in place, and he’d brought in Simpson Housing to guarantee them. At 12 stories, the Rowan would yield 209 lofts, almost as many as the Old Bank District itself.

But the same qualities that made Gilmore downtown’s prime mover—his blissful disregard for regular business practices—tossed the Rowan, along with his lenders and partners, into the mire. Gilmore decided to pare back a six-story parking garage in favor of a gym, a swimming pool, public and private park space, and a restaurant. Michael Costa, president of Simpson Housing, didn’t find out about these changes until Gilmore notified the building’s lender, Fannie Mae. According to Costa, Fannie Mae “went off the deep end.”

“Tom has wonderful ideas,” Costa says, “and we champion every one of those ideas. But you can’t just unilaterally make changes like that. He has this great vision, but if you want to get that vision done, you have to live up to your promises.”

A few weeks after Costa said this, his company sued Gilmore to dissolve the Rowan partnership and force the sale of the building. The lawsuit alleges a pattern of mismanagement that alienated two lenders, jeopardized Simpson’s own considerable stake, and left the Rowan “dead in the water.” Earlier this spring Gilmore expressed confidence that Gaw would buy out Simpson’s Rowan share through friendly negotiations. The good feelings are apparently gone. The lawsuit contends that Gilmore’s firm knowingly pushed Simpson and its affiliates into financial jeopardy “as leverage in an attempt to obtain Plaintiff’s partnership interests at less than market value.”

Gilmore explains the lawsuit is merely a means for Simpson to protect itself if Gaw’s purchase doesn’t go through by June 15, at which time Simpson’s bonds will be called. Gilmore has no doubt that Gaw will close the deal. While he understands why Simpson has to protect itself by blaming him for the project’s delays, he says he’s a little taken aback by the lawsuit’s allegations of foot-dragging. “Far be it for me to besmirch anybody’s name,” Gilmore says, “but Simpson is the slowest group of human beings I’ve ever run into in my life. I’m surprised they can actually take a crap, because they need to get so many approvals.”

Simpson is not the first Gilmore partner to become an adversary. Indeed, Gilmore’s most bitter enemies are those who collaborated most closely on his downtown dream.

After his partner Charles Loveman served his intended purpose—arranging millions in city loans and tax credits—he and Gilmore split up in April 2001. Gilmore alleges that Loveman began telling people that the firm was going out of business. Gilmore then sued Loveman for defamation. Gilmore is legally barred from discussing the terms of their settlement, other than to say he’s “very happy.”

“I believe at the end of the day, right of wrong,” he continues, “Charles’s dreams got shattered. I’d venture to say that I wasn’t the guy who shattered his dreams. His dreams got shattered like ships run onto shoals.”

“My life is far from shattered,” says Loveman, who is now executive director of a nonprofit that renovates and builds homes for low-income families in Pasadena. “I’m very glad that I am not part of that company.” During his two years with Loveman, Gilmore managed to develop his Old Bank District. Since Loveman’s departure, he’s produced no follow-up. “I’ll let the record speak for itself,” Loveman says, “about what was accomplished during my tenure.”

The National Trust for Historic Preservation was nearly another victim of Gilmore’s vision. In 2001, a few months after Gilmore addressed the organization’s annual conference, the trust rewarded him with a $750,000 loan to rehabilitate several of his buildings—the largest loan in the trust’s history. Gilmore defaulted the next year, and the trust moved toward foreclosure. The process was halted at the eleventh hour when Gaw advanced Gilmore a million-dollar emergency loan. “That was going to cause a whole domino effect,” Gaw says. “So I made him a loan, probably in one week, to take out the National Trust and get the situation resolved.”

Gilmore still seethes at the National Trust. “All of a sudden,” he says, “they became so white-bread, so nonprofit in the had sense of the word. And I was furious. I was like, ‘Oh, I get it, you’re armchair preservationists.’ It was one of those things like, ‘I’m sorry, other than my obvious hyperbole of how great this is an going to be, isn’t it pretty much clear that this is the most difficult thing anybody has done in L.A. in a long, long time?’ And it was like, ‘You’ve got a measly half a million bucks in this thing. You’re trying to kill me for it and wreck our name?’” (“The bottom line,” says John Leith-Tetrault, director of the trust’s Community Partners Program, “is that we went into a deal with Tom and ultimately we were paid back. As far as we’re concerned, that’s the end of the story.”)

The contractor that renovated the Old Bank District proved Gilmore’s toughest combatant. Frank Gamwell of Encino-based PCM fought him for two years, until 2003, when an arbitrator awarded the company $857,000 for unpaid work. As usual, though, Gilmore won the public relations war. In the Downtown News, he called Gamwell a “carpetbagger from the Valley.” Speaking to the L.A. Times, Gilmore said, “My personal opinion is that [PCM] did absolutely awful work, and I am outraged that they could make any money from us.”

“That crippled our business,” Gamwell says. “It still cripples our business. It cripples our business to where we are pretty much only doing our own work fight now, our own developments—and not through choice particularly.” Five months after the arbitrator ruled in PCM’s favor, Gilmore hadn’t paid. To Gilmore, that summer day when sheriff’s deputies came to impound the rent of the Old Bank District on Gamwell’s behalf was no humiliation but his finest moment. “When our residents saw us stand outside literally like we were defending the Alamo,” he says, “I think that was the first time everybody got it, that this was way more than just a real estate project by some developer. I really felt as strong as I’ve ever felt in my life. I was truly—I don’t even know what the word was—honored? Humbled?”

A few weeks after the deputies made their appearance, Gilmore wrote Gamwell a check—not for $857,000 but for the $650,000 Gilmore said he could afford. “I took it in the chops,” Gamwell says. “Charles Loveman took it in the chops. The National Trust nearly took it in the chops. My problem is that he started off with all these big dreams. He persuaded all these people to do things, and everyone is giving away a little bit of their life, a little bit of their money, to keep his myth going.”

One afternoon, Gilmore conducts a tour of his undeveloped properties. Spring Street between 4th and 5th, just a block west of the Old Bank District, is still the domain of the homeless and the desperate. The facades of the Rowan and El Dorado are filthy, their entrances still sealed shut. No amount of trash picking or stem looks or public relations will make the scene any less grim.

“It sort of pisses me off,” Gilmore once said, “how most people determine the difference between genius and madness as whether you succeed or not. I’m not sure that’s always under your control. What you end up being most proud of is being tenacious. What you’re really proud of is being the last man standing. I don’t think you see that in the beginning. I think in the beginning you have no sense that at some point you’re going to be so covered with blood and guts that just being alive is a good feeling.”

Just as his stand before the sheriff’s deputies made him stronger, so Gilmore contends that all the missteps, setbacks, and long delays have been propitious. He may not have another loft to lease until the fall of ’05 at the earliest, but in the end, his inability to follow up the Old Bank District these past three years while thousands of other units have been approved is a happy means of keeping his vision pure. “If it hadn’t gone so slow,” he says, “it would have gotten artificial real fast.”

In his estimation, the other developments will only enhance everything he has done and everything he will get around to doing. This is still his moment. The hurricane, the lapsed loans, the lawsuits, the crises he fought his way through—all of them were and are a matter of necessity. “Rich guys with a balanced portfolio and an impeccable track record don’t do shit like this,” Gilmore says. “It’s kind of like saying, ‘Why did Lenny Bruce have to use such foul language?’ It’s inherent in the process. It’s how it has to be.”

But rich guys are doing “shit like this” now—and chaos is not inherent in their process. It is they, with their efficiencies and solid financing, who will dominate and redefine L.A.’s historic core—and may well leave Gilmore behind.

The downtown Gilmore describes is not today’s downtown but the downtown of 2000. That was a downtown ripe for the dreamer and the gambler, a downtown where guts, audacity, the visionary’s solitary grasp of the karmic it, could triumph over every known reality, because all of downtown’s long-held assumptions had never been more false, were just waiting for the visionary to come and prove them wrong. But that is a downtown gone now, as vanished from the landscape of Los Angeles as that Victorian mansion Isaias Hellman built for himself 128 years ago at 4th and Main.