The Boston Red Sox are staring down another self-inflicted wound as Opening Day approaches, and the front office’s missteps have placed an impossible burden on Roman Anthony.

Although they added Willson Contreras, the Red Sox lost out on major players like Alex Bregman, who were a significant part of the 2025 lineup. Ken Rosenthal recently talked about how the Red Sox lost significant names, didn’t add a lot of firepower, and have put a lot of pressure on Roman Anthony to produce a record season.

“Alex Bregman would have made a Beltré-like contribution… if the Red Sox re-signed him.”

Rosenthal continued, “But this team appears at least one hitter short even if… Roman Anthony turns into David Ortiz, which seems to be the Sox’s expectation.”

The Boston Red Sox last won the World Series in 2018, convincingly at home. Since then, contract negotiations have repeatedly created tension between players and executives inside Fenway Park.

Several stars departed despite strong production, leaving visible gaps across the roster. Front office decisions increasingly prioritized caution instead of matching elite market expectations.

Fans remember celebrating 108 wins, then watching stability slowly disappear in the following seasons. Everything truly changed when Boston traded Mookie Betts to the Los Angeles Dodgers in 2020.

Betts delivered immediately, winning the 2020 World Series during the shortened pandemic season. He even helped the Dodgers win back-to-back championships in 2024 and 2025, proving Boston’s painful miscalculation again.

Meanwhile, Boston received Alex Verdugo, Connor Wong, and Jeter Downs in the exchange package. Only Wong remains today, while Betts accumulated MVP votes and postseason dominance.

Years later, Boston repeated similar mistakes during tense Alex Bregman contract negotiations in the offseason.

Bregman reportedly warned Boston about stronger offers from multiple competing franchises. Boston issued a take-it-or-leave-it proposal, believing Scott Boras lacked serious alternative leverage.

Bregman then signed with the Chicago Cubs, ending Boston’s offseason strategy. His departure removed the leadership in the clubhouse for which Bregman was credited by young players like Roman Anthony and Ceddanne Rafaela.

That leadership mattered most for rookie Roman Anthony during the breakthrough 2025 season.

Anthony posted 140 wRC+, ranking among baseball’s best hitters with 300 plate appearances. He recorded 2.7 WAR across 71 games, just like David Ortiz did in his first season with the Red Sox. During the July Philadelphia series, Bregman personally helped Anthony adjust his hand positioning. Anthony responded, hitting .323 with .945 OPS over the next 34-game stretch before injury.

Anthony’s rise continued after Team USA selected him following Corbin Carroll’s injury news.

Carroll fractured the hamate bone, forcing a roster change weeks before the WBC. Reportedly, Alex Bregman was a strong advocate for selecting Roman Anthony to fill in for Carroll.

But Alex Bregman will not share clubhouse mentorship during Anthony’s crucial development phase.

That absence quietly increases pressure on Anthony entering a demanding 2026 season.

Projections still expect Anthony to produce between 115 and 124 wRC+ during sophomore campaign. They predict improved contact, reducing his 27.7% strikeout rate slightly in the 2026 season.

Meanwhile, this spring training is also going to add a lot of pressure on Anthony to perform, especially with him batting in the leadoff spot. But it looks like Roman Anthony is ready for the challenge.

Roman Anthony reacts to batting in the leadoff position for the Boston Red Sox

Manager Alex Cora plans to use Roman Anthony as Boston’s primary leadoff hitter in 2026. Anthony posted a .396 on-base percentage, proving elite table-setting ability during his rookie season. His .292 average showed consistent contact, helping Boston create early scoring opportunities.

This decision ensures more plate appearances, maximizing production from Boston’s emerging young offensive catalyst star. Anthony’s OBP ranked among Boston’s best after his promotion from Worcester earlier in the 2025 season.

Roman Anthony has himself addressed Cora’s decision: “If that’s what AC says gives us the best chance, I’m all in.”

That response showed acceptance of responsibility usually reserved for experienced clubhouse tone-setters and leaders. And his willingness matters because leadoff hitters influence momentum during opening innings in every game.

Boston struggled to score early during the postseason sweep loss against the Yankees in the Wild Card round. Anthony, having a high OBP, directly improves Boston’s chances of scoring runs this season. Fans now watch eagerly, believing Anthony can spark victories from the first pitch again.