Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits a single during the first inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images Brad Penner-Imagn Images
Things are really starting to heat up around Major League Baseball.
We’re past the midway point in November meaning that December — and the Winter Meetings — are very close to us now. The Winter Meetings will begin on Dec. 7th, but the first big signing of the offseason has already happened. The Seattle Mariners were the culprit and signed Josh Naylor to a five-year, $92.5 million deal.
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The gates are open. So, who will be the next big domino to fall? For Boston Red Sox fans, all eyes are on Alex Bregman. The three-time All-Star was everything Boston could’ve hoped for in 2025. ESPN’s Jeff Passan shared that the Red Sox unsurprisingly “love” him and “won’t close the door on a reunion,” but reported that the Detroit Tigers, Chicago Cubs, and Philadelphia Phillies are other teams to watch for him.
“The Red Sox love Bregman, who opted out of the final two years and $80 million of his contract, and won’t close the door on a reunion despite having Marcelo Mayer ready to play third,” Passan wrote. “Detroit and Chicago, which pursued him last winter but came up short, will rejoin the fray, with Philadelphia lurking as it juggles multiple potential paths.”
Detroit and Chicago don’t come as much of a surprise here from Passan. Those two pursued Bregman last offseason, but lost out to the Red Sox in the sweepstakes. Philadelphia has been a team that has been speculated a lot, but this isn’t speculation here. This is arguably the top insider in baseball mentioning the National League East champion Phillies in the mix for him. That holds a lot of weight.
It’s been clear since before Bregman opted out, that there would be stiff competition for him. This update from Passan continues to confirm as much.
Boston arguably is in a much better position than both the Tigers and the Cubs right now. The Tigers won 87 games in 2025 and now have been in trade rumors with Tarik Skubal. The Cubs won 92 games, but now could lose Kyle Tucker. The Phillies are the team here that’s scarier. This is a team that won 96 games and has enough firepower to go toe-to-toe with the Los Angeles Dodgers, especially if they were to land Bregman.
Ahead of the Tuesday deadline to add players to their 40-man roster to protect them from the Rule 5 draft, the Boston Red Sox made a number of moves, including designating first baseman Nathaniel Lowe and right-hander Josh Winckowski for assignment.
Players who were not on 40-man rosters by the deadline are eligible to be selected by another team in the Rule 5 draft on Dec. 10.
The Red Sox traded two left-handed relievers, Brennan Bernardino and Chris Murphy, sending Bernardino to the Colorado Rockies for minor league outfielder Braiden Ward, and moving Murphy to the Chicago White Sox for Ronny Hernandez, a minor league catcher.
Boston also sent right-handed reliever Luis Guerrero to the Tampa Bay Rays for utility infielder Tristan Gray and shipped right-hander Alex Hope to the Seattle Mariners for catcher Luke Heyman in an exchange of minor leaguers.
The Red Sox added three players from Triple-A Worcester to the big-league roster: right-handers David Sandlin and Tyler Uberstine and left-hander Shane Drohan.
Signed in mid-August after being released by the Washington Nationals, Lowe provided a lift in Boston, hitting .280 with two homers, six doubles, 16 RBIs and a .790 OPS in 34 regular-season games. Overall, the 30-year-old hit .228 with 18 homers and 84 RBIs in 153 games with the Nationals and Red Sox.
Winckowski, 27, posted an 0-1 record and a 3.86 ERA in six games for Boston in 2025. In 11 2/3 innings, he had nine strikeouts and five walks. He was sent to the minors in late April and ultimately had his season end due to a right elbow flexor strain that ended his season.
The 33-year-old Bernardino finished 4-3 with a 3.14 ERA in 55 outings (three starts) this season, his third with Boston. In 51 2/3 innings, he struck out 43 and walked 26.
Murphy, 27, missed the 2024 season after Tommy John surgery and did not make his 2025 debut until June 28. He was 3-0 with a 3.12 ERA in 23 games, with 30 strikeouts and 20 walks in 34 2/3 innings.
The 25-year-old Guerrero appeared in 13 games for the Red Sox in 2025, going 0-1 with a 4.15 ERA, 10 strikeouts and 14 walks in 17 1/3 innings.
Drohan, 26, had an impressive 2025 campaign, going 5-2 with a 3.00 ERA, 77 strikeouts and 21 walks in 54 innings between Class-A Greenville (three starts) and Worcester (12 games, 11 starts).
Ranked as the Red Sox’s No. 10 prospect by MLB Pipeline, the 24-year-old Sandlin went 9-6 with a 4.50 ERA, 107 strikeouts and 40 walks in 106 innings between Double-A Portland (17 games, 13 starts) and Worcester (15 games, one start) last season.
Uberstine, 26, went 6-5 with a 3.58 ERA, 137 strikeouts and 41 walks over 120 2/3 innings between Portland (six starts) and Worcester (19 games, 15 starts) in 2025.
As for the players the Red Sox received in their trades, the 26-year-old Ward posted 57 stolen bases while hitting .290 with two homers, 37 RBIs and 74 runs between Double-A Hartford (53 games) and Triple-A Albuquerque (44 games).
Hernandez, 21, has yet to play above Class-A, posting a .262 batting average, 28 doubles, one triple, five homers and 80 RBIs in 176 games the past two seasons at Kannapolis.
The versatile 29-year-old Gray made his major league debut with the Rays in 2023. He played 30 games for Tampa Bay last season, hitting .231 with five doubles, three homers and nine RBIs while seeing playing time at every infield position.
Heyman, 22, has yet to play professionally after the Mariners selected the University of Florida product in the 14th round of the 2025 draft.