Zell and the Tribune Company required anyone who was interested in buying the team to heavily finance their purchase and to allow the Tribune Company to maintain a five percent stake in ownership for several years going forward. One prospective buyer who quickly withdrew from the process told me "it was the most complex financial transaction he had ever seen," with another telling me that he wasn't willing to jump through all of the hoops that the deal required. However, the Ricketts family stayed the course before eventually reaching their breaking point. They told the Tribune and Zell in the summer of 2009 to either make a deal or they, too, were going to withdraw from the process. At that point, according to sources, the deal quickly moved towards completion.
"Minimizing tax liability with debt financing was the No. 1 goal of Tribune Company management and Sam Zell in selling this asset. That alone made it a tough deal for many of the interested parties to handle. Add in the fact that the world markets were on fire so financing was very difficult to obtain at that time. Whoever was going to buy the Cubs -- from Mark Cuban, to John Canning, to any of the other interested parties -- was going to have to play under those rules. That narrowed the playing field quickly. Plus, do you really think that [MLB commissioner] Bud Selig, who is one of the smartest guys around, would have allowed the Cubs, a premier franchise, to be operating under a risky structure? No way," a former ownership candidate told me.
