No, he didn't, but he bought a company that owned the Cubs and that investment plummeted in value, as did his own net worth. You can talk about write-offs all you want, but there is a tremendous financial risk at stake here and some people are without question losing money. Zell's purchase of the Tribune was not your typical case study in major league baseball ownership. He bought a company that happened to own the team, and then tried to flip the team. We have no idea how much Zell valued the Cubs portion of the purchase, nor how much the Cubs were worth when Zell bought them. Everyone knew that the price was going to be high, but until there were actual bidders everything was just speculation. Ownership of a major league baseball team has been very profitable for most of the owners and is generally seen as a safe investment. Not only do they get to depreciate the value of the franchise and retain all of/if not most of the profit every year for the first 15 years, when they do sell they only pay the long term capital gains tax, which is substantially less than income tax. Also, they do enjoy the ability to write-off items for gain, but in the Ricketts case, I don't see how writing off anything would help them considering the amount of depreciation they will be entitled to take.