Copyright Newsweek

The Boston Red Sox took a risk by going after Alex Bregman in free agency last winter. Bregman is heading toward the backend of his career, but the Red Sox paid him like a superstar in his prime. This contract ended up paying off and then some as the star third baseman was the team's top player for most of the season. Bregman played so well that he was comfortable enough to opt out of his contract in an attempt to sign an even bigger contract in free agency. CBS Sports' RJ Anderson recently predicted Bregman would sign a massive six-year deal worth $192 million in free agency this winter. "Bregman inked a three-year pact last winter worth $40 million annually. In reality, it was a series of one-year arrangements that allowed him re-enter the market when he wanted thanks to opt-outs," Anderson wrote. "I have to imagine Bregman clears the deal Matt Chapman signed with the Giants last year for six years and $151 million. "My question is if he's able to also top the $31 million AAV that Rafael Devers received as part of his extension with the Red Sox. (Because, you know, it's not like Bregman and Devers are connected in any other way.) I'll guess yes, albeit barely." The Red Sox should aggressively pursue Bregman, but it would be hard to stomach a deal this large. Bregman is already 31 years old. He's going to be 32 years old by the beginning of next season, which means he'd be signed to a $192 million deal until his late 30s. At this price tag, the Red Sox might hesitate a little bit. Either way, they're likely going to be in the mix for the slugger.