After years of underachievement, the Boston Red Sox are finally back in the playoff hunt. Currently possessing the second AL Wild Card spot, if the season ended today, the Red Sox would play their hated rivals from the Bronx, the New York Yankees. Although Boston has lost their last two games, a three-game winning streak preceded it. Third baseman Alex Bregman's first season with the Sox has been a strong one thus far. The former Houston Astro could opt out of his current contract this winter. MLB Network spoke with insider Jon Heyman on Bregman's best potential fit in free agency, and shared Heyman's take on X, formerly Twitter.

“What could Alex Bregman's potential free agency look like?” posted the league network on Saturday. “‘I think he fits Boston perfectly… it does feel like Boston is the best fit.'- @JonHeyman.”

It's easy to see why Heyman said the Red Sox would be Bregman's best fit. The 31-year-old is nearing the tail end of his physical prime. However, his skillset is one that should age well, particularly at Fenway Park. After the trade of former franchise star Rafael Devers to the San Francisco Giants in June, Bregman has once again become a clubhouse leader, like he was in Houston. Can Scott Boras, the third baseman's agent, work out a deal with the Boston front office to avoid an opt out this winter? Or will Bregman once again explore free agency?

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Can Red Sox hammer out new deal with Alex Bregman, Scott Boras?

Sports agent Scott Boras talks on a cell phone before a game between the Colrorado Rockies and Los Angeles Dodgers at Dodger Stadium.
Mandatory Credit: Kirby Lee-Imagn Images

Boras is notorious for letting his clients explore free agency rather than sign an extension. The majority of the time, that is the tactic that baseball's super-agent likes to take. Even though Bregman will turn 32 in March, there are still plenty of teams that would pursue him on the open market. The Yankees would certainly be one, as the trade acquisition of Ryan McMahon before the deadline hasn't worked out as well as New York would have liked.

Whether it's the Red Sox, Yankees or another team, the likelihood of Bregman not going to a contender is slim. Based on his age, it feels like a resigning, especially if both sides can strike an agreement before the opt out. For now though, the focus is on Bregman helping lead Boston back to the postseason. Will the Red Sox finish the deal and clinch October baseball in the coming weeks? If so, don't be surprised to see the third baseman remain at Fenway Park past this season.