By all accounts cinematic and sentimental, Leonard "Boogie" Weinglass is a playground scrapper from way back. An ace on the ball field, the basketball court, the track, agile with his fists, he hails from an old school of hard knocks and hard fun.
Brainy and ferociously competitive, he comes across as a man who lives to win and remains unapologetic about his exploits.
All of which makes the hearts of Orioles fans race at the thought of this brash Baltimore-born success story -- who parlayed a sidewalk jeans boutique into a multi-million dollar retail chain -- sitting in the owner's sky box.
But the colorful exploits that make him so tantalizing to fans may render him undesirable to baseball officialdom. A body of written and unwritten rules, authored largely after scandals, sets out guidelines about who can and can't own a baseball team.
And before he buys, the man who for years has profited from his anti-establishment reputation must now undergo a character check nearly as rigorous as that to which vice-presidential candidates are subjected.
Baseball officials are bound to question a profile of Weinglass in last December's "Gentleman's Quarterly" that Weinglass says is inaccurate. The article speaks of a personal "slump" during which Weinglass "lost $1 million in six weeks, gambling on the 1982 pro football exhibition season, and the baseball playoffs and World Series."
The article is one of several published accounts of Weinglass' gambling activities. Friends have also recalled his past penchant for wagering -- something that is viewed dimly by baseball authorities.
In an October profile of Weinglass in The Sun, his former wife, Joanie Young, suggested a history of gambling as well. In the piece, she related that during their brief marriage in the early 1960s, her husband "would lose $5,000 at a clip, and we just didn't have it."
In response, Weinglass told The Sun, "Gambling was definitely part of my life." He went on to say, "I think I have it under control, pretty much."
In an interview yesterday, Weinglass said that he doesn't recall saying that he had a gambling problem to control and he never ran up $1 million in gambling debts.
"It is just not true. I never had a gambling problem. How the heck does someone start a chain of stores and get up to 800 stores with a gambling problem?" Weinglass said.
Weinglass sought to downplay his reputation, saying it was largely the exaggeration of friends and journalists. His gambling was always for small-stakes and only among friends, although it did involve baseball games, he said.
"I don't even kibitz anymore," Weinglass said.
"You don't get to be on the New York Stock Exchange by being a seedy underground character with some bad habits," he said, adding that he changed his ways about 10 years ago, when he started a new family.
The 49-year-old Weinglass, founder and chairman of the Joppa-based Merry-Go-Round Enterprises Inc., spends most of the year in Aspen, Colo.
This week, Weinglass publicly expressed interest in buying the franchise. Eli S. Jacobs, who has owned nearly 90 percent of the team since 1989, announced a few weeks ago that he had hired a Wall Street firm to assess some offers he has had for Baltimore's baseball team. The price being sought for the team is estimated to be upward of $100 million.
Weinglass also contacted his childhood friend, filmmaker Barry Levinson, now living in California, who said he is very interested in co-owning the team with him (and possibly a few other investors, though he and Weinglass would be the major owners). Their years growing up together in Baltimore were featured in Levinson's movie "Diner."
"Boogie Weinglass personifies what Americans are supposed to be all about. He's Horatio Alger," said Mike Warren, owner of a local bettors' service, and basketball buddy of Weinglass'.
Historically, the baseball commissioner takes seriously even the most tenuous connections to gambling, legal or illegal. Players and officials are not supposed to even associate with gamblers.
"He will be scrutinized," said Gene McHale, a former president of the New York Yankees and now head of a sports marketing and consulting group called American Sports Associates.
McHale is not familiar with Weinglass, but said team owners, who must approve team sales, look closely at the character and history of all would-be owners.
"Donald Trump would probably not be approved because of his ownership of casinos," McHale said.
But, he added, the rules have been relaxed in recent years. Advertising for state lotteries and other legal gambling, banned by a former baseball commissioner, Bowie Kuhn, are now allowed in stadiums.
"You wouldn't see anything chiseled in stone. It's on a case-by-case basis," McHale said.
The rule book provides for a one-year suspension when a player, umpire or official bets on a game in which he is not participating. Anyone betting on a game in which he or she is participating faces a permanent ban. The baseball commissioner is given broad powers to interpret those rules.
Sometimes, such as with former manager and All-Star player Pete Rose in 1989, the allegations involve betting on games in which the individual is participating. Other times the offense has seemed milder, such as when former stars Mickey Mantle and Willie Mays were banned in 1983 after being hired to promote casinos in New Jersey. In 1970, Detroit Tigers pitcher Denny McLain was twice suspended for "associating with gamblers."
"We generally frown upon involvement with gambling," Jim Small, a spokesman for baseball commissioner Fay Vincent, said in an interview on baseball ownership in general.
In an affectionate and admittedly "embellished" memoir about the "Diner Guys," the loyal, feisty clique immortalized in Barry Levinson's "Diner," Chip Silverman chronicles Weinglass' frequent wagering and minor-league hustling.
"He was a colorful guy who would do anything on a dare or a bet, and would usually succeed at every crazy stunt he attempted. He was also a hustler, a gambler and what people then termed a degenerate, yet he was probably more of an anti-hero than anything else," Silverman wrote.
In another "Diner Guys" excerpt, Silverman related a high school football coach's dislike of Boogie "for selling football pools." In another passage, Boogie "began to gamble serious money," Silverman wrote.
Yesterday, Weinglass said the book is "all a very exaggerated thing . . . I don't know what he's talking about."
Levinson said he does not think Weinglass' history will hurt their chances.
"That was quite a while ago. And it's not like that's how he made his living or anything. He's a successful businessman now," Levinson said.
Weinglass maintains that his betting was never with bookies and always for small amounts. "If I'm guilty of that, so are hundreds of millions of Americans," he said.
"A lot of people have nothing better to do than to gossip and speculate, especially if it's negative," Weinglass says of his gambling reputation. "I've done a lot of charitable things. I'm a good boss. I'm fair. I just want to have some fun."
Warren, owner of the bettors' service, says, "In his day as a handicapper, he had a very, very good opinion . . . In any kind of sport, he has a sense of it."
"I don't know him as a bettor," Warren says. Of Weinglass' alleged gambling problems, Warren says, "I think that was many, many years ago."
At the track, Weinglass "is a $2 bettor," he said. "I don't think it's an issue, people who are trying to make an issue of it, shame, shame on them."
Said attorney and friend Daniel Cohen of Weinglass' gambling, "I think he's got it completely under control. He wouldn't do anything to jeopardize the ownership of the team. He always could afford to gamble, unfortunately . . . I know that from what I've heard, when he did gamble, he gambled big."
But, Cohen said, Weinglass "has never hung around with gamblers or fixers or people like that."
Friends and acquaintances agree that Weinglass' knowledge of baseball, his loyalty to Baltimore, ability to build winning business teams and willingness to spend money on the team, would make him a great owner.
"I think it would be an advantage to have a local investor," said Charles Benjamin, a Baltimore clothing retailer who once worked with Weinglass at Merry-Go-Round. "He would definitely make some changes in the ballclub . . . [and] come up with things that would make the team very exciting."