In 1981, the Tribune Company purchased the Chicago Cubs from the Wrigley family for $20,000,000 and expects to sell the club this winter for a sum anywhere between $450 million and $750 million, depending on concessions made for the state of Wrigley Field and whether or not the damn governor is going to somehow end up buying it anyway.

On its own, this would be a not-too-shabby 2,250 percent return on the Tribsters’ initial investment, although one could argue current owner Sam Zell may not make a dime considering his $8.5 billion leveraged buyout of all Tribune Co. assets has since turned into an estimated $13 billion in debt – although Zell himself is only on the hook for $315 million, considerably less than even the most conservative estimate of what the Cubs’ next owner will pay for the privilege.

In 2002, taking a cue from Tribune and hoping to stay somewhat ahead of the grim outlook for its core industry, the New York Times Company took up a 17.5% stake in the New England Sports Ventures group which purchased the Boston Red Sox, Fenway Park, and 80% of the New England Sports Network. The Red Sox certainly took off, and the Times Co. will no doubt see a healthy profit on their initial $75 million investment when they find the right buyer, but the Times, like the Tribune, faces a dire financial market throwing the dirt atop an already decomposing media market. The best either company can hope for is to stop the bleeding, which seems odd considering their holdings are in two of the most marketable franchises in all of sports.

The obvious conclusion is that if the Cubs can’t save the Tribune, and if the Red Sox can’t save the Times, then baseball is not as big as everyone thinks it is; had it any might, the revenue generated from the sale of such a lucrative asset could theoretically bail out such poorly performing companies in such a floundering industry.

Where the Times and Tribune companies got it wrong, however, was not in their timing, nor in their execution, but rather in their approaches to capital build-up. The Red Sox, prior to the new ownership’s wise marketing of the club, were for all intents and purposes Just Another Baseball Team; ditto the Cubs, although the PR job the Tribune gave them will probably remain unsurpassed for some time – possibly forever.

Case in point: the New York Yankees. For nearly as long as there has been the major league system, the Yankees have been famous. Call it tradition, call it savvy, call it unfair or exploitative or just plain evil, the Yankees have been the winningest, richest team in baseball for nearly a century. On the strength of that their ownership group, Yankee Global Enterprises LLC, had the foresight to take the momentum of their late-1990s dynasty and launch the $2.90-a-subscriber YES Network. YES, which has exclusive broadcast rights to Yankee games, Yankee documentaries, Yankee retrospectives and other Yankee-centric programming, has quietly become a $340 million-a-year operation and, more surprisingly, the single most valuable arm of the entire Yankee operation.

How did they pull this off? How did the Yankees outsmart the New York Times and Chicago Tribune and their wheelbarrows full of Pulitzer Prizes? Simple: by building the marketing machine around the product, rather than building the product around the marketing machine. Having an established moneymaker and then building a sales pitch seems much more logical than using a variably profitable enterprise to prop up a rapidly devalued one.

But, you know, it probably sounded like a good idea at the time.