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.