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. Thanks for explaining my point. There might be a few owners losing money, but the vast majority are making a ton of money. TV rights and MLB merchandising provide the majority of the cash. I doubt that owners make "a ton" off of sports teams. if that were the case, why wouldn't more businesses buy sports teams? Most of the buyers are people who are already rich. Teams tend to derive their value more from the ability to resell them at a higher price and the people who are willing to buy them. If you're making a solid profit every year, enjoying tax breaks, and your investment is appreciating yearly, I would say you're making tons of money. The owners prove that when all of a sudden they "find" $100 million to pay someone like Holliday. It's all a game between Boras and the owners. When you look at the owners that are in trouble financially, it's usually their problems outside of MLB that are messing them up.