Boston Red Sox all-time best free agent signings

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The BoSox Injection staff takes a look back at the all-time best free agent signings in Boston Red Sox history.

Mandatory Credit: Peter G. Aiken-USA TODAY Sports

Free agency is a gamble fraught with significant risk and just like at the casino, the house usually wins. When elite talent hits the free agent market they expect to be paid based on past performance, despite that every win they helped secure during their last contract unfortunately doesn’t carry over to the new one.

In an ideal world teams would offer contracts based on what those players are projected to be worth for the duration of the contract, but that rarely works in an environment where teams with deep pockets are forced to bid against each other for the services of a limited number of premium talent. The laws of supply and demand often work in the player’s favor, which is why we see so many long-term deals extend well beyond a player’s prime.

The Boston Red Sox find themselves in such a predicament after finalizing a lucrative deal with free agent pitcher David Price. Their desperation to acquire an ace to anchor their rotation led the Red Sox to spend $217 million on a 30-year old pitcher, which is a significant u-turn from the philosophy ownership held as recently as a year ago. As one of the best pitchers in the game over the last several years, Price will be worth every cent of his contract for as long as he remains in his prime, but the expectation is that the Red Sox will need to keep paying him like an ace even after he hits his decline years. Will Price produce enough on the front end of his deal to have been worth it by the end? It’s too soon to tell.

Such is the gamble of free agency. It may not end well, but that doesn’t mean that the price they pay won’t be worth it in the end. The Red Sox don’t have the best track record when it comes to signing expensive free agents, particularly in their recent history, but it hasn’t been all bad.

Let’s look back at the ten best free agent signings in Red Sox history to prove that despite the risks of paying market prices, free agency isn’t always a losing bet.

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