Red Sox Owner John Henry Faces ‘Monumental’ Backlash if Offseason Fails Again

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John W. Henry, Owner of the Boston Red Sox

The Boston Red Sox front office has largely been sluggish in the Major League Baseball offseason for the past six years. Now, if the Red Sox ownership led by hedge fund billionaire John Henry fails to make a significant move heading into 2024, Henry and the team’s management will face a “monumental” backlash from a fan base unwilling to forgive another season of mediocrity, according to one top Boston media personality.

Fans appear to agree. In a recent thread on the SoxProspects.com message board several commented saying that Henry “doesn’t care anymore and doesn’t care what the fans think, either. It’s all about the money and he knows the fans will keep coming and handing him money, so why add to the payroll?”

Another called him “an aloof billionaire,” while yet another stated that Henry “comes off as a man who has no plans in investing in the Red Sox like he once did.”

A Six-Year History of Failure to Add Big Name Talent

In fact, the most memorable move the Red Sox have made since signing prolific slugger J.D. Martinez right before the 2018 season was a negative one — trading away 2018 American League MVP Mookie Betts. The outfielder was both the team’s best player and a fan favorite, but the Red Sox shipped him to the Los Angeles Dodgers on February 10, 2020, rather than pay him what it would take to keep him out of free agency.

Betts, who won his MVP award in the same year that the Red Sox won 108 regular season games and cruised to their fourth World Series championship of the 21st Century, went on to win two World Series in Los Angeles where he signed a 12-year, $365 million contract.

Since 2018, the Red Sox have finished in third place in the AL East twice and last place three times. In 2021 they placed second and made a surprise playoff run to the League Championship Series.

In the 2022-2023 offseason, the Red Sox again lost a star player beloved by the fan base when shortstop Xander Bogaerts — who was part of both the 2013 and 2018 World Series-winning Red Sox teams — was allowed to depart in free agency. The native of Aruba signed an 11-year, $280 million deal with the San Diego Padres.

The Red Sox attempted to compensate by locking up home-grown, heavy-hitting third baseman Rafael Devers to an 11-year, $331 million contract extension. Their only major outside acquisition that year was former Colorado Rockies shortstop Trevor Story. Under previous head of baseball operations Chaim Bloom, the Red Sox handed Story a six-year, $140 million deal.

But halfway through that contract, Story has played only 163 games for the team due to a series of injuries and a Tommy John surgery.

The offseason prior to the 2024 season, under new Chief of Baseball Operations Craig Breslow, produced no significant signings or trades and saw the Red Sox payroll drop to $176.4 million, ranking 12th of the 30 MLB teams.

By comparison, the world champion, 108-game winning 2018 team had the highest payroll in the game at $235.6 million, the equivalent of a $299 million payroll in 2024, adjusting for inflation.

2024 Sparking Fears of More Squandered Opportunity

The Red Sox have already lost out on the top free agent on the market, Juan Soto, and one of the top pitchers, Max Fried who signed with the arch-rival New York Yankees. As of Tuesday they were reported to be “readying an offer” for the other top free agent pitcher, Corbin Burnes. But by Wednesday, they reportedly had pivoted downward to a possible reunion with their own free agent, Nick Pivetta.

So what happens if the Red Sox fail to sign Burnes? According to longtime super-fan, podcast host and Red Sox television personality Jared Carrabis, in a view apparently shared by a large segment of fans, nothing good — especially after the front office pledged that this offseason would be different.

“After all the hype this winter, the backlash will be monumental and perhaps unforgivable,” Carrabis wrote on his social media accounts. “Last straw kinda stuff with a fraction of the fan base and I don’t think I could blame them.”