Michael A. Liberty - Maine Business Entrepreneur & Real Estate Investor

The small-town kid becomes one of Maine's most successful real-estate developers

Michael A. Liberty Yankee Magazine ArticleMichael A. Liberty, who grew up in a small town in Maine, has made millions rebuilding the state in his image. Depending on whom you talk to, he's either a character from a Horatio Alger story or Donald Trump with a Maine accent.


The folowing article, written by staff reporter James Dodson, originally appeared in the August '89 issue of "Yankee Magazine" in New England and is reprinted here with permission.



by James Dodson
© Yankee Magazine - August 1989

What people first notice about him is the hair, thick, dark, lustrous—a perfectly symmetrical Euro-coif that doesn’t give an inch even in a heated Sunday morning basketball game.

For a big man, 6’2” and 200 pounds, Michael Liberty easily negotiates the court of a high school gym in Yarmouth, Maine. He dodges a defender, stops at the three-point line, and pops. With 20 clicks on the clock the ball arches toward the rafters and slices cleanly through the net, tying the score at 64-all.

Battling on the court for the championship of the Yarmouth Men’s League this Sunday in March are teams called the Buckley Group and Cole Farms.  Among the aging players are several former Maine hard-court standouts, including two small-college all-Americas. But the most hustling guy on the court may be Michael Liberty, known by his friends as Michael, to the business world as “Mike,” the small-town kid who grew up to become a flashy millionaire almost overnight, one of the most controversial real estate developers in the history of Maine.

Besides his talent for making millions on land deals, Liberty is a deadly three-point shooter, and in the overtime period Liberty tries two long-range bombs but misses both.  Live by the big shot, die by it: this seems to be a dynamic Liberty understands as well as anybody. Cole Farms, undefeated until now, loses the championship game 77-69.

Afterwards, Liberty saunters over to the bleachers and accepts a sweatshirt from a handsome brown-haired woman who has been quietly watching throughout—Gail, his wife, who is five months pregnant with their first child.

He pulls on his sweatshirt. “There was a time when I would get depressed over this, you know?” he says. “But now I know it’s just a game. I shrug it off.  There’ll be other games.” He helps his wife off the bleachers. “Hey,” he suddenly says, “that must be one sign of getting older. I’m learning to lose with grace.”

Michael Liberty - Business investment and real estate developmentHe’s joking, but don’t kid yourself. Michael Liberty hates to lose at anything, even weekend-warrior basketball. On paper, conservatively estimated, Michael Liberty is worth at least $300 million, a land and investment empire built dizzyingly fast in less than a decade. Just 29, he enjoys the privileges of several successful lifetimes.  He owns a vintage Rolls Royce, a Mercedes, and wears $400 custom-made Italian suits. He lives in a 10,000 square-foot house next door to the small house where he grew up in Gray. He water-skis with champions in Florida and bird hunts with millionaires in northern Maine. He owns several snowmobiles and a Jacuzzi for eight.

In the roiling 1980s game of Maine real estate development, there are other successful players in the Pine Tree State, and a few have even made more money wheeling and dealing Maine land than Michael A. Liberty. But you can’t put a name and face to them the way you can to Michael Liberty. In his short working life Liberty has built shopping centers from Portland to Bangor, industrial parks, office buildings and two major condominium projects that created a philosophical firestorm on the coast of his home state. He owns part of a professional hockey team, the Maine mariners, and all of the richest short-track motor speedway—Oxford Plains Speedway—in America. He and his partner, David Cope, 34, also own Juniper Farm, a high-tech embryo transfer facility near Gray that ships frozen embryos from super Holsteins around the world—“The Larry Birds of the bovine world,” Liberty boasts.

The Liberty portfolio rolls on and on: New England franchise rights to T.G.I. Fridays, one of America’s most successful restaurants; four Burger Kings with possibly more to follow; a chain of Country Hospitality Inns; 2,500 mobile home sites in five states; part of Katahdin Corporation, which may well be on its way to becoming the biggest manufactured housing firm in America—a company projected to be worth $100 million in the next four years.

A lesser mortal might be content with that, but not Michael Liberty. He is always on the move, looking for the opportunity to pop the big shot from Three Point Land, a process that undeniably is changing the face of Maine. “As a kid who grew up on the outside,” he admits, “I had to bust my butt to make everything. I guess I always have something to prove.”

And he is still proving it. At the beginning of this decade Michael Liberty made his first million. He was not yet 21. The media fashioned him as a wonder kid, an overnight sensation, though Portland’s old business guard thought he was just a flashy punk from Gray. But then the millions began to pile up, as did the Liberty projects. The old guard finally accepted him just in time for the public view of Liberty to radically change.

“Depending on whom you talk to,” says Portland city council member Pamela Plumb, summing up his rags-to-riches career, “Mike Liberty is either regarded as a Yankee Horatio Alger story or else as an absolute symbol of what has happened to Maine in the past decade, the ultimate opportunist and despoiler of the state, Donald Trump with a Maine accent . . . The truth may be somewhere in the middle or a combination of both.”

For all his material success, Liberty knows he has an image problem: that for better or worse, he is probably the most passionately admired, oddly reviled young man in Maine.

It might be different if he were from away.  Then developer Michael Liberty would be easy to rip—the coiffed hair, the GQ threads, the persuasive hustle with which he closes deal after deal. But Mike Liberty is Maine, in some ways as common as pasture grass, which in large part explains why he is who he is—and why so many people eventually came to respect and resent him.

Before he was a legendary dealmaker, he is quick to point out, he was a dreamer in a town of 3,000 where his father Arthur ran a brickyard and he and his two half-brothers, Billy and Jimmy, and a sister, Deborah, shared a cramped ranch-style house perched on Route 24 in Gray, on the way to Oxford Plains Speedway.

“We weren’t exactly poor, but we didn’t have many comforts. My brothers were into cars and motorcycles, which they bought and paid for themselves. Racing was a big deal—it was a way to be somebody. I used to sit on the grass at the speedway and think that that would be my ticket.” While his friends raced snowmobiles on Gray’s Crystal Lake, Mike took a job haying at a dairy farm and pumping gas in the center of town.

Something terrible happened the year he turned 14, an event, he says, that prematurely hurled him into the adult world. While riding his motorcycle days after his high school graduation, Mike’s half-brother Jimmy Finney, with whom he shared a bedroom was struck and killed by a car less than a mile from home. “A guy came into the station,” Liberty remembers, “And said, ‘Hey, man, did you know Jimmy Finney just got hit by car—he’s all over the road.’ He didn’t know we were related. My mother was right behind him when it happened. She saw the whole thing. My mother told us she couldn’t bear to live in the house anymore; she was having terrible nightmares. One Sunday we were a normal family, and one event changed everything. The whole world fell apart.”

Billy Finney, an all-state soccer player on scholarship to Husson College, suddenly dropped out of school. When their grandfather died two months later, Mary Liberty abruptly packed up and moved home to Winchester, Massachusetts, to care for her mother. “She said she wouldn’t ever move back to Maine.” Soon after, Arthur Liberty sold his brick business and joined his wife, and sister Deborah married, leaving 15-year-old Michael alone in the empty house.

It was a three-year period of isolation that created a profoundly confused and insecure teenage. “I was the only kid I knew who had an entire house to himself,” he says. “After awhile I guess I went a little crazy. I thought about running away, even suicide. But something saved me from it—and that gave me a sense of self-respect I’d never had. It made me hungry to win, to earn respect.”

Maine basketball - Michael LibertyThat something was schoolboy basketball. The story is fairly commonplace in Maine business circles how the short, chubby kid from Gray grew 10 inches in one summer and worked harder than anyone else to earn a starter’s spot on the Gray-New Gloucester High School basketball squad. During his senior year he moved out of his parents’ house and into a mobile home with Billy. Basketball brought Michael Liberty the attention he wanted. It made him somebody. A friend from that time remembers, “Michael always talked about how he was going to be somebody important. Even then, he always had some kind of deal going on. He talked big, moved fast. Most of it was talk, but everyone knew he was different—something unusual drove him. I think because of his background he had a compulsion to be accepted and admired. That’s what he was really selling.” His peers believed what they saw and voted Liberty, despite his low grades, “Most Likely to Succeed.”

A family photograph from 1979 shows a thin, sallow-faced, shaggy-haired Michael Liberty standing rigidly behind a small wooden counter next to a pinball machine. By then most of his friends had gone off to college or technical school leaving Gray’s Mister Most Likely behind for the second time in his life. Liberty’s days on the basketball court were over, and he would have to find a new game to conquer. He opened a small sub shop.

Every day except Sunday he rose at six and opened at eight. He closed shop at midnight and drove to Portland for Italian rolls, then came home and cut up peppers and onions until three, when he went to bed. Part of the reason his mother finally came home to Gray, he says, was to give him a hand running his sub shop. “But I was killing myself for $125,” he remembers. “And I think that’s when I really hit rock bottom. I realized that meatballs were taking me nowhere fast.

Michael A. Liberty’s rock-bottom life changed dramatically when a house builder in Gray noticed his hustle and commented that he could work half as hard and make twice as much money pitching real estate.

The Reagan eighties had dawned, and there were two Maines distinctly evolving—or, more correctly, two Maines that had always quietly coexisted were moving dramatically farther apart. There was the Maine of woodlots and house trailers, and there was the Maine of postcard vistas and vacation homes. Developer wasn’t a profane word in those days. In almost no time, Liberty found himself moving from one Maine to another, from “Michael,” the kid, to “Mike,” the hard-edged businessman.

He sold his meatball shop for $3,000 and borrowed $15,000 from his father and bought a 50-acre dairy farm in New Gloucester, which he subdivided into five building lots and sold. He reinvested the $10,000 profit from that deal into another real estate project and promptly lost it. “But I learned a lesson. I realized real estate was tough, and you could lose as quick as you could win. You had to be smarter than the next guy. I wasn’t formally educated but discovered an ability for seeing and making deals. I studied everything I could find on the subject, attended every seminar I heard of, became a fixture at selectmen’s meetings.”

He also heard about something called real estate syndication—a way to finance projects with other people’s money. In 1979, at age 19, he convinced two doctors to finance the purchase of an $80,000 inn on Sabbathday Lake. The deal paid off handsomely for the doctors, and Liberty was off and running.

Perhaps the most obvious transformation occurred then. He still looked like an insecure kid from Gray. Before making his next sales pitch to a group of doctors at Maine Medical Center, Liberty went to a Portland clothing store and bought himself a high-ticket Italian suit. He had his hair styled. “I was scared to death,” he admits. “I was really selling myself and my business judgment to them—why would they give a kid so much money to invest? Clothes were my only protection, my armor.” The doctors liked Liberty’s style and cracked open their checkbooks.

In 1980 Liberty met David Cope, son of a successful Portland builder. Cope was polished, college educated, a married father of four—a detail man with connections who preferred to avoid the limelight. By temperament and style, Cope was perfectly suited to playing Butch Cassidy to Liberty’s Sundance Kid in the emerging Wild West days of Portland real estate.

Their first buy, for $650,000, was a dowdy office building in the center of Portland. To make the down payment, Liberty sold 15 shares at $15,000 each. “Local businessmen said we were crazy to pay that much for the building, but four years later we sold it for nearly twice what we paid.”

Michael Liberty dairy farm - embryo transferUsing federal loans, the newly formed Liberty Group built elderly and middle-income housing—30 major projects worth about $30 million over the next five years. In 1984 Liberty bankrolled a friend’s idea to start up a high-tech embryo transfer company that created the ritziest cow barn in New England and filled it with two dozen world-class Holsteins that produced four times the volume of milk of the average dairy cow. “People said I was brain dead to start up Juniper Farm,” he recalls. “But having worked on a farm, I knew frozen embryo technology was something whose time had come.”

Suddenly it appeared that Liberty was somebody to be reckoned with on the Portland business scene. Maine newspapers reported that investors couldn’t line up fast enough to invest in Liberty Group projects. “Big deals or rumors of big deals were going down every day over lunch at the Cumberland Club,” recalls a Maine business editor, “and Liberty was portrayed as some sort of backwoods wonder kid whose touch was golden.”

As ballplayers say, the game was on. As with all infant superstars, the sideline press loved his natural flamboyance, his candid style. Sports celebrities and politicians courted him, as did arts groups and charities. He responded by donating thousands to political campaigns, the arts, and social charities. He bought a new basketball floor for the University of Maine at Orono. He became a registered Republican and even commented to friends that someday he hoped to be governor of Maine. Maybe when he was 30.

Everybody knew Michael Liberty loved to joke around, but he wasn’t kidding.

It wasn’t until Liberty built two luxury condominium projects on the coast of Maine that the broad public image of him radically changed.  At Signal Point in Boothbay Harbor, Liberty and Cope bought a derelict boatyard and broke ground for a 36-unit luxury condo project that originally had the enthusiastic support of town selectmen.  Then the Army Corps of Engineers charged violations of wetlands permits, and local lobstermen complained that the project’s marina would damage area fishing. When the town’s code enforcement officer insisted that foundations of two of the project’s buildings were too close to the shore, Liberty reluctantly admitted the mistake and ripped up the concrete and started again.

Even Liberty critics feel it was an honest mistake, a technical oversight; Liberty believes he could have won a protracted legal battle against the town fathers. But in any case the effect of the controversy had a tarring effect. “Rightly or wrongly,” says Pam Plumb, “a lot of people concerned about Maine’s waterfront suddenly saw Mike Liberty as a person at the forefront of what was happening to the coast of Maine—the fear became rampant that it was going to be gobbled up by wealthy developers. A lot of people decided it was time to put on the brakes.”

At that moment on the waterfront in Portland, Plumb points out, half a dozen development projects were underway or about to start, including the Liberty Group’s 91-unit Chandler’s Wharf project. The scope of that project combined with his youthful brio and high public profile made Liberty a logical target for Maine’s antidevelopment movement.

“To a lot of people he represented greed,” says Phyllis Austin, a report specializing in environmental affairs for Maine Times. “And he came along at a time when passions were really stirred up. Here was a guy who wanted to put up monster developments that would take away waterfronts that traditionally belonged to everybody.”

In late 1985 a woman named Karen Sanford spearheaded the formation of a group calling itself “Keep the Port in Portland.” “Our philosophy was that the Portland waterfront was a valuable public resource, too fragile to be taken over by developers like Mike Liberty and made inaccessible to fishermen and the public.” By that point, Sanford points out, Chandler’s Wharf was nearing completion—and almost 90 percent pre-sold. So their focus became two other projects, Liberty’s proposed 200,000-square-foot Long Wharf project and another developer’s even larger 300-condominium project proposed for Eastern Point. When the city granted approval of these projects, the group brought together a coalition of neighborhood activists, environmentalists, and fishermen and waged a two-year legal battle that resulted, in 1987, in passage (by a 2-to-1 margin) of a referendum that placed severe marine-use-only restrictions on future waterfront development. It effectively imposed a ban for five years on the very kind of commercial and residential development Liberty was heavily invested in. Liberty eventually challenged the referendum in the Supreme Court of Maine and lost. Last December he threw in the towel on Long Wharf, reportedly having lost millions.

By that time the game had already turned mean and nasty. The media that had once applauded the local-boy-makes-good angle began questioning the credibility of his projects and his motives. During construction of 100 Middle Street—a large atrium-crowned office structure that Liberty promised would be “the most beautiful building in Maine”—several news stories cited a history of alleged code violations and painted a picture of a company moving too loose and fast.

Liberty’s bad press developed a roll of its own. In the summer of 1988 Liberty, now owner of the Oxford Plains Speedway, put on two outdoor concerts by a heavy metal group that were good for his ledgers but a disaster for his image. The crowds enraged local residents whose attempts to enforce town ordinances were rebuffed by Michael Liberty. When a subsequent Grateful Dead concert attracted over 100,000 “deadheads” per show (only 37,000 tickets had been sold), local pressure mounted and Liberty filed suit. But later he dropped charges and announced there would be no more rock concerts. Ever. A pledge that to many sounded more like “maybe.”

For perhaps the first time in his professional life, Liberty had no interest in talking to the press, whom he regarded as hostile and vindictive. Behind the scenes, Liberty and Cope took steps to smooth out their tangled image problems: they trimmed excessive personnel and beefed up their technical staffs to better research future projects and avoid legal snafus with local governments. Liberty adopted a lower profile and hired a public relations expert from out of state to arrange and screen his interviews, a fact that further estranged him from the local press. “This is Maine, after all,” says on influential business editor. “It’s not New York or even Boston. Mike had no problem talking to Fortune magazine, but he wouldn’t grant the Maine Sunday Telegram a personal interview. That really hurt him. That only deepened the resentment.”

“For the first time it made me stop an really think things over, “ Liberty says, “and try to see what coming so far so fast had really meant. At the low point of all the publicity,” he explains, “when there were so many crazy and false stories circulating, I called up Senator Bill Cohen. He’s somebody I respect. He told me, ‘Michael, like it nor not, you’re a public figure, and they can say anything they chose about you—even if it’s not accurate. You’d better develop a tougher skin.’”

So he did. Liberty decided the even closer scrutiny of politics wasn’t for him. He moved too fast, he spoke too freely. Better to stay in the same game, he realized, and adopt a different strategy, which he also did. There were other worlds to conquer, namely the roughly 20 million acres of Maine that weren’t located on the Portland waterfront. Mike Liberty essentially bid good-bye to the bright lights of the city and went back to the country.

Ten years ago Michael Liberty lived in a house trailer. He likes to say he knows what it feels like to be poor in Maine and to want something better, the American dream, a home of one’s own. That was the philosophical gist of what he told 800 real estate people packed into a Bangor steakhouse to hear Liberty speak one night last spring. It was apparent that a shrewder Liberty had emerged from his Pyrrhic affrays of the recent past. He explained that his company was headed back to where it began—to affordable housing.

Maine housing constructionOver speculation and subsequent moratoriums had ruined southern Maine, he explained, “sending rents skyrocketing and eroding the industrial base and pushing affordable housing out of the market—and most of the work force that goes with it.” From where the developer stood, the Bangor area, two hours north of Portland, looked like the new land of Everyman’s milk and honey. It had an international-sized airport and a terrific industrial base that had attracted such linchpins as L.L. bean’s new half-million-square-foot production facility. It wasn’t coincidental that Liberty hoped to build two large retail centers, a mammoth industrial complex, and several low-to-middle-income housing projects in the region in the years to come. It made for a banquet room full of happy real estate brokers. “Michael Liberty is probably the leading player in Maine real estate,” explained one broker who claimed he’d studied the vicissitudes of Maine real estate for 30 years. “Guys like him used to come and go—dealmakers, high rollers. They say this kid is different. He’s taken his licks and he’s come back stronger than ever. Who knows how far a guy like him goes.” The guest speaker got a rousing five-minute standing ovation.

Several nights later the developer stood at the door of a posh ballroom at a new country club outside the city limits of Portland and greeted 300 friends (“a friend for each of his millions,” quipped a guest), investors, and business associates. The affair was billed as a party to celebrate Liberty Group’s record sales year in 1988. It was a significant evening for Mike Liberty. Not only was he once again adopting a more visible public persona, but the figure he cut was even appealing to a former nemesis, the Maine Sunday Telegram, which earlier that week had published a glowing profile of the refocused Liberty group, observing that the developer may have been caught in the crossfire of an antidevelopment backlash. “My life is nice now, it’s simple,” he told the paper. “I have fun. I’m doing a lot of business, and I’m not reading about it. It’s fun to be respected.”

Around the ballroom, as a jazz band played, a Who’s Who of Maine business people, lawyers, CEOs, and bank presidents nibbled butterfly shrimp and sipped free Scotch and paid homage to several Liberty Group projects—drawings of Signal Point and Chandler’s Wharf, future shopping plazas in Sanford and Auburn, a detailed map showing the firm’s plans for affordable housing in Maine.

Not shown—but very much on the developer’s mind—was an ambitious Sanford subdivision project soon to be proposed in which Liberty and Cope hoped to build 800 low-to-middle-income-level houses on 300 acres. It would be the largest affordable housing subdivision in Maine, he explained to a pair of interested businessmen and a reporter, one of the largest, in fact, in New England. “We’ve got a housing crisis in northern New England, and we are going to take the lead in guaranteeing affordable housing,” explained the developer, sounding an awful lot like a salesman whose heroes are public office holders.

One of the businessmen dryly observed that the idea sounded great—but hell, wasn’t it incredibly complicated and risky? Most developers wouldn’t dream of tackling a project that size and scope.

Liberty only smiled. The man who, for better or for worse, is changing the face of Maine had his game face on. Win some, lose some, it’s really all a game, making deals, making millions. What’s got some people delighted and others worried is that Michael Liberty is not yet 30.