Red Sox Facing Stiff Alex Bregman Competition Before Winter Meetings

The signs are pointing to some significant competition if the Boston Red Sox want to retain Alex Bregman for the 2026 season and beyond.

Rumors have been out there about the Bregman sweepstakes for a while, but with the Winter Meetings approaching, things are starting to heat up. On Friday, Bruce Levine of WSCR-AM and 670thescore.com reported that the Chicago Cubs and Detroit Tigers are "attractive" options while pointing to the fact that Bregman doesn't have a draft pick attached to him this year with the qualifying offer.

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The Red Sox have stiff competition

Oct 2, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) is forced out by New York Yankees shortstop Anthony Volpe (11) at second base in the ninth inning during game three of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

"Alex Bregman this free agent year, without losing a draft pick, (qualifying offer) is more attractive to teams like the Cubs and Tigers. .821 OPS despite playing only 114 games," Levine wrote. "Cubs offer last winter was 4 years, $115 million. Right-handed pop might be the way to go for Cubs."

Boston obviously is a fit for Bregman and should bring him back. The Cubs and Tigers specifically have been speculated about because of their interest in him last offseason. This note from Levine aligns with reporting from The Athletic's Patrick Mooney and Sahadev Sharma from Thursday night that the Cubs have "renewed interest" in Bregman.

"The Chicago Cubs are preparing for Kyle Tucker’s exit as a free agent, ready to give rookie hitters Owen Caissie and Moisés Ballesteros the runway to develop at Wrigley Field," Mooney and Sharma wrote. "Pitching remains the club’s primary focus, but team officials have not ruled out the idea of adding to a solid group of position players.

"Once again, a particular name stands out under consideration: Alex Bregman. After a failed bid to sign Bregman during spring training, the Cubs have shown renewed interest in the All-Star third baseman, according to sources briefed on the club’s offseason planning."

Again, Boston arguably is the best fit. The Red Sox beat the Cubs and Tigers for Bregman last offseason when a draft pick was attached to him. Last offseason, the Tigers reportedly offered Bregman a six-year, $171.5 million deal. Last offseason, the Cubs reportedly offered Bregman a four-year, $115 million offer. The Red Sox won out, but if the Cubs and Tigers were willing to make those offers with a draft pick attached, what about now without one? Nerve-wracking, to say the least.

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