Inside The Red Sox

Blue Jays-Alex Bregman Smoke Emerges At Worst Possible Time For Red Sox

Not a good time, Toronto...
Apr 29, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) rounds second base after hitting a solo home run against the Toronto Blue Jays during the first inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images
Apr 29, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) rounds second base after hitting a solo home run against the Toronto Blue Jays during the first inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

There are always a few teams no team wants to face in a free-agent bidding war, and as shocking as it might be to some, the Toronto Blue Jays are becoming one of those teams.

For years, the narrative about the Blue Jays was that they couldn't convince free agents to take their money. That proved false when Dylan Cease signed with Toronto last month, and the Boston Red Sox will only be worse off with each subsequent big name the Blue Jays can land.

Meanwhile, it's also been a stressful week for Red Sox fans with regards to the Alex Bregman sweepstakes, as the Arizona Diamondbacks emerged as surprise suitors on Tuesday. But if the Diamondbacks are a five out of 10 on the threat level scale, the Blue Jays have to be considered at least a seven.

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Red Sox could face stiff competition if Blue Jays are in on Bregman

On Friday, ESPN insider Jeff Passan told ESPN New York's Michael Kay on his radio show that he believes the Blue Jays are "very much in the mix" for Bregman, which hasn't often been mentioned as a fit throughout the winter.

"I don't know how much the Arizona thing's going to work," Passan told Kay. "I think that the Blue Jays are very much in the mix there. It’s a little bit tougher for them because they’ve had Ernie Clement and Addison Barger at third base. Both have done well there.

"I think the Blue Jays understand chemistry matters and leadership matters. I think they benefited greatly last year from the team they had on the field. Alex Bregman, say what you will about him, is regarded as a very good clubhouse guy. And somebody who could be a leader for that team going forward. So I could see Bregman going there.”

Toronto must also think about bringing back its longtime shortstop Bo Bichette, who the Red Sox had a Zoom meeting with before the winter meetings. Plus, the Blue Jays hosted superstar right fielder Kyle Tucker on a visit last month. So if there's interest in Bregman there, the good news for the Red Sox is that he still may not be the club's Plan A.

But the success of this Red Sox offseason comes down to whether Boston can land at least one, preferably two big bats. The Blue Jays sniffing around Bregman, especially if they have the capacity to sign two of the names above, seems to increase the odds that it could be zero.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org