The main goal every team has to win the world series. The Yankees got CC and immediately went out and won a championship. Not only that but CC ended up being a massive part of why they did. I don't think any Yankees fan is is going to or should regret giving him that deal. He gave them 4 solid seasons and was a big part of their world series team. Lets say the Brewers have a really good team just missing an ace in 2018 and decide to sign Jake Arrieta to some HUGE contract. Then the Brewers go on to win the 2018 World Series title behind a dominant Jake Arrieta. If he then give of 3 disaster years at $30mil each are you really going to say, "Wow I wish the Brewers never signed him." Heck no you aren't...you are going to be waving that world series flag. It is just another example of how big markets can just comfortably know half the contract will be a disaster and most likely not horribly effect them. The Yankees can pay CC $25mil to be a #5 starter, not shed a tear, and still win 87 games. Now I am by no means saying this is a fool proof way or guarantee a world series championship. Winning a world series, like many other sports, is mostly hitting your stride at the right time and a lot of luck. What is undeniable is that big markets compete more, get to the playoffs more, and stay in playoff contention many more years than a small market could. Now at the end of the day a lot of times a big payroll team doesn't win the world series. Then again neither do the Brewers and at least those big markets get to compete almost every year while small markets go through painful rebuilds losing star players.