Whenever MLB GMs set out to sign a player to a massive free agent contract, there is always quite a bit of risk involved. The risk is typically intensified as additional years are placed on that contract without opt-outs. The Angels contract that was tendered to Albert Pujols appeared to be a form of torture for everyone involved. It became abundantly clear that Pujols was not going to be the player the Angels had envisioned very early on, and they would be forced to endure that for many years.
Pujols is just one example from a lengthy list of free agency contracts reaping with regret. The main factors that typically define a contract as “risky” include: Health, degradation of performance, and fit with the team that signs them.
Teams aim to sign the players with the least amount of risk associated with them, but in order to build a contender you sometimes have to accept the risk in order to reap the reward. Heading into the World Series, I wrote how the Phillies were built upon a series of risky contracts that went their way. Kyle Schwarber and Bryce Harper could have been included in a list just like this in their respective year of free agency.
It’s not to say that these players will not work out for their teams, but there are many scenarios where the fan bases are ruing the day they were signed. Oddly enough, everyone included in this list is an absolute superstar, and all 3 of them are very likely to be in the hall of fame discussion.
As is Albert Pujols, but it doesn’t change the fact that he was handed an extremely risky contract that didn’t work out.