Despite their best efforts, the Boston Red Sox were unable to retain Alex Bregman and bring him back to the team for the upcoming season. Now, a radio talk show host has criticized the team for missing out on Bregman, and much of it centers on team owner John W. Henry and the team’s Chief of Baseball Operations, Craig Breslow.

Mark Dondero of 98.5 The Sports Hub offered his take on the team’s current condition and criticized John Henry, the team owner, as “not interested in winning” in baseball anymore.

“She’s moved on. She’s married. She’s making love to this other guy, and they’re having kids and a life. That’s John Henry. He’s moved on. He’s not interested in winning the way he used to be. That life that you yearn for, that you remember, is over.”

Despite having the money, John Henry seems unwilling to spend more to sign high-level free agents for his team. He failed to bring in free agents like Pete Alonso.

Notably, the Red Sox have been the only team this offseason without a big-league name on the roster so far. The only names they have managed to sign are Willson Contreras and Sonny Gray.

Henry, however, is focused on building the team through its farm system. While using the farm’s talent is a good move, it takes time for players to gain relevant experience. Meanwhile, the team suffers in the regular season and postseason due to a lack of veteran players.

Such moves might lead to the feeling that he is not interested in winning.

John Henry has also failed to retain his players.

This past season saw him trade away Rafael Devers to the San Francisco Giants as a cost-cutting move, similar to how the team dealt with Mookie Betts in February 2020. Such cost-cutting measures have led Henry to operate the team with a “small-market” philosophy, which, in turn, is affecting the team’s performance in both the regular season and postseason year after year.

“And the energy that I spend, thinking about it or talking about it or what can they do, oh, they get this guy, they could get this bat and bring him in and pair him with this person. And you get a pitcher at No. 2, and we could be right there. No. She’s with someone else. She’s not at the bar anymore. She’s not looking for somebody anymore. It’s over. She shut it down. They’ve shut it down. They’re done with that life,” Dondero said.

With Alex Bregman gone, it remains to be seen how the new Boston Red Sox team of John Henry will perform in the upcoming MLB season.

How did Craig Breslow Muck Up Alex Bregman?

Craig Breslow’s muck-up of Alex Bregman led to him departing the Boston Red Sox and joining the Chicago Cubs. The Red Sox fumbled Bregman’s deal by being unwilling to give him a full no-trade clause as part of his new contract. The team also cited organizational policy as the reason for not agreeing to a full no-trade clause. Additionally, the amount they offered him was lower than the Chicago Cubs’ offer, according to Peter Abraham of The Boston Globe. Naturally, Bregman did not like the deal and departed from the team.

Bregman also received a $70 million deferred payment as part of his five-year, $175 million deal with the Chicago Cubs. While the Red Sox also offered deferred payments in their contract, the structure was different. Like the Cubs, the Red Sox also offered Bregman a five-year deal.

However, their deferred payment was scheduled to stretch out over decades, according to Chris Cotillo and Sean McAdam of MassLive.

Top Stories

MLB Refuses to Come to Blue Jays Star’s Aid as Ross Atkins Refuses to Budge Amid Disagreement

Boston Threatens “Mutiny” Against Red Sox as Roman Anthony left to Dry After Alex Bregman Exit

3 Reasons Bo Bichette’s Offseason Market Seemingly Collapses After Blue Jays’ Sudden Shift

Mets Give Up Tatsuya Imai Pursuit as David Stearns Targets $200M Free Agent Ace: Report

Bo Bichette’s Toronto Return Fades Fast as Blue Jays–Red Sox Face Fierce Threat From AL East Rival: MLB Rumor

Unfortunately, this decades-long payout of the deferred amount increased the disparity between the two offers and reduced the overall value of the Red Sox’s proposal for Alex Bregman. Moreover, the Red Sox’s “aggressive” offer for Bregman was much lower than the Cubs’ offer, leading him to choose Chicago over Boston.

Craig Breslow and the Boston Red Sox now face scrutiny over Alex Bregman’s deal and his departure from the team. Whether the organization makes up for it by adding some big names for the upcoming season remains to be seen.