ASPEN, COLO. — ASPEN, Colo. -- A funny thing happened to Boogie Weinglass on his way to this week's meeting of NFL owners. He grew up. Oh, he's still America's most unlikely multimillionaire, a brash but big-hearted Baltimorean who instinctively wipes his fork on his napkin before eating at his own diner and can't seem to fend off business success with a stick. But the ponytail has grayed, the kids are starting school, and Leonard Michael Weinglass, 50, has begun thinking about life beyond the Hilltop Diner. And that life, like the fabled high school hangout, should include football by the gravy-stained platesful, he says. "I would consider it a lifetime dream for a poor kid who became rich to give something back to his town," Mr. Weinglass said between bites of a Boogie Club at "Boogies," his trendy diner/clothing store here. He and five investors comprise one of the three groups that plunked down $100,000 application fees to own a National Football League team in Baltimore, should the city win a franchise in the league's scheduled 1994 expansion. The idea of Mr. Weinglass and other members of the Hilltop "diner" crowd -- a clique of football-crazed Baltimoreans popularized in a 1982 film of the same name -- returning the game to town is the stuff of, well, movies. His entry raised two immediate questions: Does his group have the cash? And will the image-conscious NFL go for a blue-jeaned, self-professed ex-gambler who hired the Temptations, Marvelettes and Drifters to play at his own 50th birthday party? The answer to both questions appears to be yes. After initial reservations, many officials connected with Baltimore's football procurement drive have come to view the chairman of the Harford County-based Merry-Go-Round clothing store chain as the strongest of the city's three bidder groups. For one thing, although he's no angel, he seems to be telling the truth when he says his image is an exaggeration of a wild, if somewhat extended adolescence. And despite all the stories about his fighting, gambling and womanizing, the Baltimore native was never convicted of anything more serious than a misdemeanor, according to a review of public records by The Sun. There are some old timers here who view Mr. Weinglass as a moneyed interloper, but he is mostly held in high standing in his mile-and-a-half high adopted home town. In Aspen, he is known for philanthropy, not philandering. One NFL official familiar with the league's background check on Mr. Weinglass said "he checked out well." Another said the league is prepared to "judge him as a man," not as the youth he once was. Perhaps most important of all, Mr. Weinglass and his investors have the highest net worth of the three Baltimore groups, said Herbert J. Belgrad, chairman of the Maryland Stadium Authority, who, as lead man in Baltimore's bid for an expansion team, is familiar with the applications. The other investor groups are headed by developer Malcolm Glazer and author Tom Clancy. NFL owners, who vote on all entrants to the fraternity, are scheduled to meet this week to shorten the list of cities contending for the two teams the league wants to add. Representatives of all three owner groups, including Mr. Weinglass, are expected to attend the meetings in Phoenix. Most observers predict Baltimore will make the short list but will have a tougher time beating out Charlotte, N.C., and St. Louis. Supporters of Mr. Weinglass' bid talk about the "new" Boogie, a self-made businessman worth $150 million. He is a father of three who lives on a $5 million, 42-acre ranch perched above this Rocky Mountain resort with five live-in employees, a Jacuzzi and an eight-foot, stuffed Kodiak bear. He has, friends say, followed many Americans his age across the generational divide. Even in business, he has successfully gone from peddling marijuana paraphernalia to $2,000 leather jackets. Time as well as checks Many of this city's fur-lined residents write checks for local causes -- Saudi Prince Bandar bin Sultan dropped a half-million on the Disabled Ski Challenge -- but few donate the time and interest that Mr. Weinglass does, said former Aspen Mayor William Stirling, who has opposed Mr. Weinglass on some political issues. Mr. Stirling, now president of Stirling Homes, said, "You find him at the door greeting kids at the youth center" that was built in part with Mr. Weinglass' donations. But some longtime Aspenites yearn for the mountain village that existed before Cher, Don Johnson, Goldie Hawn and other celebrities fell like an avalanche on the town, jacking up average home prices to $1 million and pulling in tourists like a ski lift. When Boogies, his unique diner/clothing store, opened here in 1987, it replaced a family rib joint called The Shaft. Residents viewed Boogies, with its Haagen-Dazs milkshakes and $75 tasseled bras, as a symbol of a Banana Republic revolution. Ever since the diner opened, locals have referred derisively to the "Boogiefication" of Aspen. But they don't seem to hold it against Mr. Weinglass personally. Dick Butera, owner of the Aspen Club, spa of the rich and famous, said, "He runs around with holes in his jeans and a ponytail and he'll make statements once in a while at a party that are outrageous. "But he's smart and very generous. He's an eccentric, but a very positive eccentric." Mr. Weinglass has long contributed, often anonymously, to causes and people in Aspen and Baltimore. The Weinglass Foundation, which he founded in 1983, has $4.4 million in assets and gives away $100,000 to $200,000 a year. Last year, it bought a Parkton, Md., quadriplegic a $32,000, specially equipped van and picked up the air ambulance fare so a California couple whose baby was born four months prematurely in Baltimore could return home. "I really see him as a blessing," said Holly Dahlman, a 21-year-old premed student at Mount Holyoke College, and a recipient of Weinglass Foundation grants. Born with severe facial deformities, Miss Dahlman met Mr. Weinglass when she gave him and some guests riding lessons at a horse ranch near Aspen. He has since paid for thousands of dollars worth of plastic surgery that was threatening to bankrupt her family, Miss Dahlman said. But then there is the "Old Boogie." In a 1990 interview with Gentleman's Quarterly magazine, Mr. Weinglass brags about romancing women in his youth while his friends watched from the closet and tells of a "slump" in 1982 when he lost $1 million gambling on the 1982 football exhibition season and baseball playoffs and World Series. Weekend gambler Also in 1990, his ex-wife, Joanie Young, told The Sun that he "couldn't stop" gambling during their brief marriage in the early 1960s. "He used to lose $5,000 at a clip and we just didn't have it. I just couldn't take it anymore," Mrs. Young said. Last week, Mr. Weinglass said he was misquoted when it was reported he lost $1 million. "I've never lost $1 million. I've never bet $1 million," he said. "For me it was a weekend thing where I would bet a guy a couple of hundred on a football game." He said he has not gambled at all for 10 years. "Diner" didn't help his image. In the reminisence about coming of age in Baltimore, "Boogie" is a sleazy character played by Mickey Rourke. At one point, the fictional Boogie is worked over by a bookie after falling $2,000 in debt, and then conspiring to sleep with the wife of a friend to win another bet. (Mr. Weinglass describes the movie as about 75 percent accurate.) In "Diner Guys," an admittedly embellished memoir of the real "diner" crowd written by Chip Silverman and sold at Boogies, Weinglass is described as "a hustler, a gambler and what people then termed a degenerate, yet he was probably more of an anti-hero than anything else." Robert I.H. Hammerman, chief judge of the Baltimore City circuit court, said, "With me in my position, we would not have stayed good friends if he had a sorted background." The judge was president of the City College Alumni Association when Mr. Weinglass was a student there and has remained a friend. "Anything illegal or immoral going on, Boogie was involved in it or heading it," he remembered. "Boogie being Boogie, he had the best. If there were four or five betting pools, his was the best. "But as far as I know, it was just small stuff around the school." Despite that, Judge Hammerman saw in the youth drive and ambition. "With three children now, it's given him a much different perspective, and I think he's becoming much more conscious of what he wants his reputation to be and to leave more than just money," Judge Hammerman said. Mr. Weinglass' only recent brush with the law was more political than moral. He opposed a 1990 referendum to outlaw fur sales in Aspen and voted against the measure by listing his downtown condo as his residence when he signed up for an absentee ballot. Prosecutors claimed his real home was his ranch, called ,, "Merry-Go-Ranch," outside the city line and charged him with two counts of voting fraud and one count of perjury. Didn't have a case A judge dismissed the matter mid-trial last fall, saying the prosecution did not have a case. "The fact that he wasn't a bad guy made this hard to prosecute. I can tell you for a fact that this town really likes Lenny Weinglass," said James Wilson, the Pitkin County deputy district attorney who prosecuted the case. Among those who feel Mr. Weinglass' chances to own an NFL team will be tainted by his colorful lifestyle is Edwin F. Hale Sr., chairman of Baltimore Bancorp, owner of the Baltimore Blast soccer team and briefly a participant in the football ownership race. "It's his persona," Hale said. "It doesn't fit the profile of an NFL owner. That's what I've heard. It's unfair. He just doesn't fit the profile of what most owners are looking for. . . . I think he'd be a terrific owner." His reputation notwithstanding, indications are that Mr. Weinglass has passed the NFL's initial background check. Three people with NFL ties who were contacted for this story said he has been cleared by the league's security department. Warren Welsh, director of security for the NFL, was not available for comment. Norman Braman, owner of the Philadelphia Eagles and a member of the committee on expansion, said Mr. Weinglass "checked out well." New York Giants general manager George Young, a Baltimore native who taught and coached at City College when Mr. Weinglass was there, said he caught him selling football pools one day. But Mr. Young says he didn't see anything sinister in Mr. Weinglass, describing him only as a "mischievous kid." "You have to judge him as a man," Mr. Young said. "He was a decent-hearted guy. He had a lot of foolishness as a kid, but he was bright." Few NFL owners know Mr. Weinglass personally. The owners' perception of Mr. Weinglass as he campaigns this week and in the months ahead could largely dictate whether they find him acceptable to their small, elite circle of wealthy businessmen. "We've had some bad experience with incompatibility of individuals," said Lamar Hunt, owner of the Kansas City Chiefs. "It's very difficult to judge in advance. We'd like to know as much as possible about everyone." Mr. Belgrad said, "My impression is it should not be an issue. . . . It would be difficult for the owners to take the position that conduct in the distant past alone [would eliminate Mr. Weinglass]." Mr. Weinglass is the third son of a pair of poor Orthodox Jewish immigrants who had come to Baltimore in the 1930s -- the father from Germany, the mother from Poland -- to escape Nazi horrors. Most of his older relatives, including both sets of grandparents, were killed in the holocaust, and family friends who visited his childhood home often had death-camp ID numbers tattooed to their forearms, he said. When Mr. Weinglass was 4, his father, Sol, was forced by tuberculosis to close his corner grocery. From then on, the family survived on charity and what little cash the boys could hustle by shoveling snow, delivering newspapers and returning soda bottles for refunds. The heating oil would often run out in the winter. "That's just the way it was. If it was cold, you wore sweat socks to bed," he said. He took seriously his father's admonition: "Don't take anything off of anybody." When someone called him a "dirty Jew," they usually found themselves dodging his fists. "When you're poor and you live in the ghetto, you either beat up people or get beat up," he said. He bounced from school to school, attending eight elementary and high schools before getting thrown out of Forest Park High for selling stolen report card blanks to fellow students. He was accepted into City College, but had to forgo athletic eligibility until he could bring his grades up. "In those days, sports was my life. I had nothing else going for me, no money, no cars, no social life," he said. He started attending classes regularly and ended his junior year in the last place anyone expected: the honor roll. That got him back onto the basketball squad and on course to graduate the next year, at age 21. After high school, he tried a variety of jobs, from hair dressing to selling clothes. He spent a few months in college, but dropped out and completed a stint in the Maryland National Guard. He married and then divorced Ms. Young within a year. Wall Street wonder He moved to Atlanta as a sales rep, peddling leather coats. In 1968 he opened a small store of his own, selling blue jeans, T-shirts and marijuana paraphernalia. His girlfriend picked the name Merry-Go-Round, which, along with blaring rock music and bell bottoms, they hoped would be hip. It worked. Despite some recent recession-related troubles, Merry-Go-Round Inc. has grown into a retailing empire of 850 stores in 38 states. It should hit $1 billion in sales by next year. Following Mr. Weinglass' philosophy, its buyers immerse themselves in MTV pop culture to stay current. Wall Street marvels at the chain's ability to keep fickle teen-agers coming back with their parents' money. Mr. Weinglass began to ease out of day-to-day management in 1979, spending more and more time at a vacation condo in North Miami Beach, Fla. It was there that he met Pepper, now 32, a cocktail waitress at the exclusive yacht club attached to the condo. They were married in 1984. The two moved to Aspen, a town Mr. Weinglass said he liked as much as a refuge from city life as for its spectacular scenery. They've had three children: Sage, 5, and 2 1/2 -year-old twins Skye and Bo. Old movie posters and photos of the family decorate the Aspen home. A downstairs weight room looks like Arnold Schwarzenegger's office and opens onto snow-capped mountains. Roaming the land are three horses, a goat, two dogs, two cats (one with only three legs), a bird and a life-size giant plastic cow. Frustrated with the food available in Aspen, he opened Boogies in 1987. Like Merry-Go-Round, the diner and attached boutique is ultra-hip. It's a cross between the Hard Rock Cafe and White Castle, a place where salesgirls in tight jeans fit customers in $400 calf-hair Larry Mahan cowboy boots. The diner is a replica of the Hilltop hang-out, down to the gray Formica counters and pink booths. Boogies is a hit with townies and tourists alike and does about $5 million a year. With Merry-Go-Round's backing, Boogies have opened in Chicago, New York, Los Angeles, Washington and, later this year, Las Vegas. Better enjoy life Amid the success, however, came an event that reminded Mr. Weinglass life is not an unending parade of chromed diners and condos. Harold Goldsmith, his former roommate and partner at Merry-Go-Round, died in a fiery airplane crash on a mountain ledge about 100 yards from the Weinglass ranch. The pilot, having missed the nearby airport, might have been attempting an emergency landing on the flat land next to the ranch. "It confirmed my belief that you better enjoy yourself," Mr. Weinglass said. "That helped spur me on to take some of my money and have some fun with it instead of dying with it." He assembled a group of investors that include not only big money but solid image: Richard Pearlstone, a philanthropist and heir of the Meyerhoff fortune; Barry Levinson, an Academy Award-winning Hollywood director; corporate chiefs David Bernstein and Michael Sullivan; and local retailer E. Douglas Carton. Weinglass puts his group's net worth at $350 million, about $150 million of that from him alone. The NFL has not set a price, but most estimates put the franchise fee alone at $100 million to $150 million. From there, start-up costs could top several million dollars a year before games begin and revenues start flowing. The NFL strongly prefers cash to credit, something Mr. Weinglass said the group can accommodate easily. "In this group there are sufficient funds. I know they have it," said A.B. "Buzzy" Krongard, chief executive of Alex. Brown & Sons, a Baltimore-based investment firm that has advised the group. Giving a tour of his mountain-top ranch last week, Mr. Weinglass, who earns $1 million a year in dividends and lease payments alone from Merry-Go-Round, seemed closer to the West Baltimore rowhouse than a map would indicate. Despite having earned millions in fashion retailing, he wore his trademark faded jeans, white T-shirt and Reeboks. He swung a 5-year-old Jeep Wagoneer, littered with children's toys, around the corners and through mountain passes. "I'll never own any jewelry. Because to me that's a lot of B.S. to show off your wealth. And I'll definitely never own a plane," he said. "I'm an everyday guy who, through hard work and having a very smart partner, was fortunate enough to make a lot of money." BOOGIE SAYS: On running a team: "I would not be a Steinbrenner type of owner. He hired good managers but didn't give them a chance. " It would make good business sense and common sense to let the pros run the team. ... We would be very good at marketing the game in Baltimore. I have a strong marketing background. We'd have some pretty good uniforms." On a team name: Would first try to buy Colts from current owner Robert Irsay. If that doesn't work, would have fan contest to select from a number of choices. One he likes: Baltimore Bombers, a name that harkens to Baltimore's war-time aviation industry. On Baltimore's chances: "I think we're the front-runner. I really do." Among competitors, St. Louis is probably the strongest, with Charlotte, N.C., showing some advantages. THE WEINGLASS GROUP Barry Levinson Age: 49 Primary residence: Los Angeles Occupation: motion picture director, writer and producer; heads Baltimore Pictures Inc., a Hollywood production company. Academy-award winner. Salary: Not public. But one industry insider estimates Levinson commands a salary of $5 million to $6 million per film as well as 7.5-10 percent of the film's gross. Annual income estimated to be $10 million to $12 million. Michael Sullivan Age: 52 Primary residence: Baltimore County Occupation: president and CEO, Merry-Go-Round Enterprises, which last year generated a profit of $22.7 million on sales of $761.2 million; director, Bank Maryland Corp. 1990 salary: $749,395 (Merry-Go-Round) Stock in Merry-Go-Round: 358,320, or 1 percent of total, as of 5/1/91, for an annual dividend income of about $72,000. Value as of 3/12/92: $3.98 million. David H. Bernstein Age: 57 Primary residence: Baltimore Occupation: chairman of Duty Free International Inc., a Ridgefield, Conn.-based operator of duty-free stores that generated a profit of $14.6 million on revenues of $105 million last year. 1990 salary: $450,000 Stock in Duty Free International: 1.3 million, or 11.5 percent of total, as of 5/1/91. Value as of 3/12/92: $60.12 million. @Richard L. Pearlstone Age: 44 Primary residence: Baltimore Occupation: Real estate developer/investor. Executive Vice President of Delta Properties Inc., consultants and developers specializing in commercial real estate; chairman of Cross Keys Asset Management Inc., a financial advisory firm; principal in Cape Development Corp., a real estate company; director, Sizeler Realty Investment Trusts. He is grandson of the late Joseph Meyerhoff, a major Baltimore developer and philanthropist. Stock in Sizeler, the only publicly reported firm among his holdings: 26,067 or .81 percent of total as of 4/5/91. Value as of 3/12/92: $273,703. E. Douglas Carton Age: 43 Primary residence: Baltimore County Occupation: Founder and owner of C-Mart Discount Warehouse, 70,000 square foot store in Forest Hill, Md. Does not release financial data, but has about 100 employees. Financial information from a variety of public records and the individuals involved; does not include private income which for most of the group members could easily exceed their publicly reported salaries.