Because They Can Play You
The Ricketts family owns the Chicago Cubs. They're a group of real-life Billy Madisons who bought a baseball team to prove something to their billionaire dad. Tom is the bumbling, pathetic figurehead—pretty much by default—and runs the team, rather appropriately, like a rich kid that's been handed everything. Meaning, he's both the wealthiest and least respected person in every room he's standing in.
Since taking over the team in 2010, the ownership group has begged the city of Chicago for $200M to "modernize" Wrigley Field. So, even if you don't care for the team, or the sport, as a taxpayer you're saddled with financing a (supposedly) private empire. Why? So the owners aren't hassled with the upkeep of their own personal money-printing-factory. If you haven't puked on your keyboard yet, the New York Times reported that Joe Ricketts (the aforementioned "billionaire dad") planned to drop $10M on an ad campaign against "government spending." In other words, the patriarch of the Ricketts clan is really against government handouts—unless, of course, that check is cut to his millionaire kids.
In the Ricketts' first two years as team owners, the Cubs have been all of 146-178. This year they're in last place and still have the second highest average ticket price in baseball ($108.70). When they're not passing the operating costs of their own business on to the City of Chicago, they're gouging their fans. And for what? The privilege of watching Carlos Marmol pepper sliders off of the backstop for the league's worst team. It's disgusting, totally unsustainable, and exactly why Ricketts bought the Cubs—they sell out every game regardless of record.