Now that Mark Cuban’s bid to buy the Pittsburgh Pirates has been officially squashed by the team’s owners, will Cuban pick up the phone and call Dennis FitzSimons to ask the Chicago Tribune Company’s Chief Executive Officer if he is about ready to sell the Chicago Cubs? Probably.

Cuban, who grew up in Pittsburgh idolizing the Willie Stargell-led Pirates teams of the 1970s, did not hide the fact that he was interested in buying his hometown team. Unfortunately, Kevin McClatchy, who also owns a national newspaper chain called the McClatchy Company, let Cuban know the Pirates are not for sale. But FitzSimons and his board may have to part with the Cubs, a decision that will have nothing to do with the team’s success between the lines. Simply put, the Tribune Company is short of money, and the Cubs franchise is a major asset that can bring in big dollars.

Depending on the price tag, Cuban would likely jump at the opportunity to own one of baseball’s most lovable – and most profitable – losers.

The Tribune Company needs a major cash infusion quickly to pay off a $1 billion IRS judgment stemming from the 1998 “reorganization” of a former subsidiary of the Times Mirror Company, which the Tribune bought out in 2000. After a court ruled that the deal was not a reorganization, but in fact a sale – which made it subject to tax laws – the Tribune Company set aside $253 million to cover a potential verdict. They underestimated the verdict by $750 million.

The Tribune Company is appealing the decision, but word on the street is that FitzSimons and the Tribune Board may put the Cubs on the market in an effort to pay off the fine. The Tribune Company has a great many assets, led by Chicago’s WGN TV, the station that carries Cubs and White Sox games and reaches some 66 million households in the US. It also owns WPIX (Channel 11 in New York), 22% of the WB Network, a piece of the Food Network, and develops TV programming.

The Tribune Company also owns a handful of radio stations and newspapers around the county, including the Chicago Tribune, Los Angeles Times, Baltimore Sun, and New York Newsday. Most of those entities are cash cows, but none more so than the Chicago Cubs.

The Chicago Tribune Company bought the Cubs from William Wrigley in 1981 for $20.5 million. Since then, despite another 24 years of futility, the club’s value has only escalated. Still, the company has been unable to secure a new stadium, which has led to a seemingly endless expansion project – 1,800 more seats are being added to the outfield bleachers as we speak, but capacity is still a relatively paltry 39,358, especially for a franchise as popular and recognized as the Cubs.

No matter the team’s record, Cubs games are events. People don’t go to the “friendly confines” just to watch a baseball game, they go for a cultural experience. If the Washington Nationals are worth $450 million for just a baseball team and a lease for a potential new stadium, what are the Cubs worth?

A better question is, if Cuban or anyone else decides to pursue the opportunity to buy the Cubs, just what will they actually get? The Cubs franchise is more than just a baseball team, and if you sold each part separately – the team, Wrigley Field, and the Tribune’s piece of the regional Chicago sports network that is owned by Comcast and includes Jerry Reinsdorf’s White Sox and Bulls and William Wirtz’s Blackhawks – the Cubs wouldn’t get that much money on the open market. Sports is a business, and in the 21st century, that business includes real estate deals (do you want to pay rent on your stadium?), television rights, and digital media capability.

But if FitzSimons and the Tribune Board decide to sell the entire Cubs franchise, including the team, Wrigley Field, and the regional sports network and TV and radio contracts with WGN, that’s an entirely different story. The sum of those parts would be extremely attractive to an investor, especially when you consider the history.

The Cubs potential sale situation compares favorably with that of the Boston Red Sox more than four years ago. In 2001, Red Sox Chief Executive Officer John Harrington, acting on behalf of the Jean R. Yawkey Trust, announced that the late Mrs. Yawkey’s 53% of the Red Sox, Fenway Park, and 80% of the New England Sports Network were for sale. Harrington eventually awarded the team to Florida Marlins owner John Henry along with his partner Tom Werner (the former San Diego Padres owner) and others including the New York Times and former Senate Majority Leader, Maine Democrat George Mitchell, for $700 million.

If and when the Cubs go up for sale, the bidding would probably start at $800 million, but potential buyers would have to demand that the deal include the Cubs’ piece of the regional cable TV network – which could be a major sticking point. The Yankees, Mets, Red Sox, and Astros have gone into the regional sports network business because that is where big money is made. If the Tribune Company refuses to sell off its part of the Comcast Sports Net Chicago, it could be a deal breaker.

Cuban, who led the crowd at Wrigley in the traditional singing of “Take Me Out to the Ball Game” on July 15, is known to want a Major League Baseball team. Having been spurned by the Pirates, it remains to be seen whether he can convince FitzSimons that the Tribune Company should sell off the Cubs. Perhaps he should ask Cubs fans, who just want a winning team, to get involved. A petition drafted by the Wrigley faithful is already going around Chicago and the Internet.

“Cubs fans on a whole,” it reads, “are sick of the ‘lovable loser’ attitude that our management seems to have. We are confident that Mark Cuban could bring a winner to the north side of Chicago. Our city would fully support him, and [he] would quickly become one of ours. If he can turn around the Dallas Mavericks, he can turn around any franchise.”