Alex Bregman, Bo Bichette, or Bust: Red Sox at the center of MLB’s stalled free-agent market

New year, same MLB free agency.

Alex Bregman remains a free agent, and a handful of teams around the league continue to express interest in the veteran third baseman. The Red Sox, the Blue Jays, the Diamondbacks, the Tigers, and the Cubs have all been connected to Bregman this winter.

As of Thursday, MLB.com’s Mark Feinsand reported that two teams are upping their pursuit of Bregman.

“Sources believe the Blue Jays and Diamondbacks may be the two most aggressive clubs in the hunt for Bregman, though a Red Sox reunion remains a possibility,” Feinsand said.

On the flip side, Feinsand believes that the Sox’ interest in Blue Jays free agent infielder Bo Bichette could be impacting their aggressiveness for Bregman.

“Last month, Bichette’s camp let clubs know that he would be willing to move to second base, news that potentially opened his market to more suitors,“ Feinsand wrote. ”The Red Sox, who have Trevor Story at shortstop, are believed to be interested in Bichette, though it may come down to whether Boston prefers him to Bregman... Bichette’s future may be tied directly to what happens with Bregman, as the Blue Jays and Red Sox are in on both players.”

Fast-forward 24 hours later, ESPN’s Buster Olney went on TSN’s “1st Up” and reported Boston has made “an aggressive offer” to Bregman.

“I think Alex Bregman is going to go back to the Red Sox,” Olney said. “They valued him last summer.”

Bregman was a perfect fit for the Red Sox in 2025, providing leadership in the clubhouse, particularly to the younger players like Roman Anthony, Marcelo Mayer, and Kristian Campbell. He tore the cover off the ball to begin the season, hitting .299 with 11 homers and posting a .938 OPS in 51 games.

In his first season with the club, Bregman hit .273 with 18 homers, 28 doubles, 62 RBI, and 51 walks, with a .821 OPS in 114 games. He missed seven weeks of the year due to a right quad injury, and upon returning to the club, he completely cooled off at the plate, hitting just .250 with seven homers and 27 RBI, and owned a .727 OPS in the second half. He also scuffled at the plate in the month of September, hitting just .216 with two homers and nine RBI with 12 strikeouts in 88 at-bats.

The Sox are in this position because Bregman opted out of his deal following the season. Bregman earned $40 million, which includes deferrals, but forfeited the final $80 million owed to him to pursue a new long-term contract with either the Red Sox or a contender.

A handful of reputable websites have Bregman getting either a five-year, $170 million deal or a six-year deal to help lower the average annual value.

If Bregman bolts in free agency, the most obvious pivot is towards Bichette.

He makes sense, especially if he moves off shortstop to play either second or third base. Bichette has also crushed the ball at Fenway Park as a member of the Blue Jays. In 35 career games at Fenway Park, Bichette owns a .329/.382/.524 slash line with a .907 OPS, slugging six home runs and 10 doubles, and driving in 30 runs across 157 plate appearances. That production translates to a 149 wRC+ and a .386 wOBA.

If Bichette moves off position to come to Boston and he slides to second base, it allows the Red Sox to move Mayer to third base. At 27, Bichette also aligns with Boston’s competitive timeline. He fits alongside Anthony, Mayer, Ceddanne Rafaela, and Garrett Crochet, and the rest of the emerging core without blocking development or forcing a short-term window.

Mayer remains a question mark, considering he’s yet to play a full professional season that doesn’t end with him on the injured list. The rookie was limited to just 44 games this past season; Mayer hit .228 with four home runs, 10 RBIs, and a .402 slugging percentage. Barring a trade, he figures to be a significant part of the Red Sox’s 2026 plans.

Boston also assigned him No. 11, Rafael Devers' old number. I may be joking, but did the Sox assign him that number due to their extensive stock of Devers' No. 11 jerseys?

If not Bregman or Bichette, one other pivot could be towards Astros slugger Isaac Paredes. The Boston Globe's Alex Speier recently labeled him a "primary target," following weeks of rumored Sox interest in him.

Paredes hit .254 with 20 homers, 15 doubles, one triple, 53 RBI, 50 walks, and a .809 OPS in 102 games last season. It’s unclear whether the Astros are looking to trade Paredes, who was the centerpiece of the Kyle Tucker trade with the Cubs last offseason.

This wouldn’t be an MLB Hot Stove rundown without mentioning the Sox link to Ketel Marte. If Breslow elected to send a king’s ransom to Arizona, Marte would immediately stop Boston’s rotation at second base.

The 11-year veteran has been one of baseball’s most complete offensive players since 2023, posting back-to-back All-Star seasons in ’24 and ’25 and slashing .283/.376/.517 with 28 homers last year.

His contract—six years, $116.5 million—is widely viewed as team-friendly, especially compared to what Bregman could command on the open market. Defensively, Marte remains reliable, ranking in the 74th percentile in range among second basemen. Any trade for Marte or Paredes will be expensive and will require additional prospect capital.

Bringing Bregman back gives the Sox another right-handed hitter to pair with Willson Contreras, who the club acquired in December for Hunter Dobbins and two other pitching prospects.

The Red Sox are in need of another right-handed bat but at the end of the day, what might make sense truly comes down to dollars and cents. 

RED SOX NOTES

The Boston Red Sox have signed outfielder Matt Frazier to a minor league deal, according to MiLB Central’s Chase Ford. 

The move adds experienced depth to the organization’s outfield mix ahead of the 2026 season.

Frazier is coming off a productive year in the Pirates organization, where he hit .305 and totaled 22 extra-base hits, showcasing a blend of contact ability and gap power. 

Originally selected by the Pirates in the third round (95th overall) of the 2019 MLB Draft out of the University of Arizona, Frazier brings versatility to in the outfield playing all three positions in Pittsburgh’s system.

He is expected to provide depth at Triple-A Worcester, where he’ll compete for playing time in an outfield group that already features Campbell, Braiden Ward, and potentially Nate Eaton if Eaton does not make the big league roster out of camp. 

The group also includes minor league Rule 5 selection Matt Lloyd, along with Tyler McDonough and Phillip Sikes.

WINCKOWSKI HEADS NORTH

Former Red Sox right-handed pitcher Josh Winckowski is getting a fresh opportunity north of the border.

Winckowski has agreed to a two-year minor league contract with the Toronto Blue Jays, according to Steve Adams of MLB Trade Rumors. The move marks a full-circle moment for the right-hander, who originally began his professional career in Toronto’s organization.

Winckowski became a free agent after he was designated for assignment and subsequently non-tendered in late November. During his time with the Boston Red Sox, he appeared in 121 games beginning in 2022 after being acquired in the trade that sent Andrew Benintendi to the Kansas City Royals.

The righty logged 11 2/3 innings last season, splitting time between Boston and Triple-A Worcester before landing on the 60-day injured list with a flexor strain in his right elbow. Had the Red Sox kept him on the 40-man roster, Winckowski would have been arbitration-eligible and projected to earn roughly $800K in 2026.

GIOLITO MOVING ON?

Red Sox free agent pitcher Lucas Giolito is coming to the realization that his time in Boston might be coming to an end. During an appearance on the Baseball Isn’t Boring podcast, Giolito discussed his focus on training and working out and preparing to pitch somewhere in 2026.

“The thing is that I’m very focused on what I’m doing,” Giolito said. ‘I used to work out four or five days a week. I’m working out six days a week now. I have a lot of stuff on my plate. There is a lot of work to be done when it comes to my mechanics, my pitch mix. I’m trying to add another pitch. I’m putting a lot of work in.”

Giolito signed a two-year, $38.5 million deal with the Sox in the final days of 2023, eventually earning his way to free agency by surpassing 140 innings in 2025. He finished that season with a 3.41 ERA across 26 starts before declining a mutual option.

Unfortunately, health derailed his opportunity to help the Red Sox in the postseason, as he suffered a right elbow injury towards the end of the regular season, prompting the Sox to shut him down for the playoffs.

The veteran righty would welcome a return to the Sox but understands that after the acquisitions of both Sonny Gray and Johan Oviedo, that may not be in the cards for the 31-year-old.

“For me, the anxiety is lessened, and all that kind of nonsense, there is less of that when you’re focused on the present and what you’re doing each and every day, rather than being like, ‘Where am I going to sign? What’s happening? What’s going on?’ I have my agent, Ryan (Hamill), who does a wonderful job. Just let him do the work. I’m not interested in hearing, ‘This team is interested in you.’ I’m not interested in hearing anything until we get to the point where offers are coming across the table.

“You get better at anything with experience. I have been through this once. This will be my second go. I will probably have a third go when that’s done. You get used to things. This goes for anything in life. You do something for the first time, it’s going to be uncomfortable. You might make some mistakes. It might be weird. But when you do it for the second time it’s going to be easier.”