5 worst free-agent contracts in Boston Red Sox history

The Red Sox have made some horrible decisions in free agency

Money doesn’t solve everything. Throwing buckets of cash at the top free-agents might seem like the simple solution but the strategy can backfire. The Boston Red Sox know that all too well with a history littered with poor investments.

Major League Baseball is structured in a way that vastly underpays their top stars early in their careers and prevents them from cashing in through free agency until they’ve already reached their peak. The best free-agents are going to command top dollar on long-term deals that will continue paying them to be stars long after their skills start to erode. That’s the nature of the beast. In order to land the top talent in free agency, teams must be willing to risk overpaying on the back end of deal. For teams that can afford to pay up, the process is typically worthwhile as long as the player performs to expectations for the majority of the contract.

Sometimes that decline comes early, turning a lucrative contract into an albatross long before the team was able to get their money’s worth. In some cases, the player never lives up to expectations.

There are several factors to explain why the Red Sox didn’t join the spending spree that captured headlines leading into the lockout. While we expect the team to make more moves once a new CBA is in place, they don’t necessarily need to be flashy. Spending recklessly in an effort to “win” the offseason doesn’t guarantee a championship and spending on the wrong players can be detrimental to that goal.

Let’s take a look back at some expensive deals the Red Sox have handed out to former All-Stars in free agency that backfired with disastrous results.