The Boston Red Sox’s offseason just took a brutal turn, and a franchise legend is done mincing words.

After coming agonizingly close to retaining Alex Bregman—only to watch him sign a five-year, $175 million deal with the Chicago Cubs—former closer Jonathan Papelbon unloaded on the front office, delivering a scorching warning that the team’s reluctance to spend could doom them to the basement of the AL East.

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Papelbon, a four-time All-Star who anchored Boston’s bullpen from 2005 to 2011, didn’t hold back during an appearance on Foul Territory.

“The front office has got to be prepared to spend,” Papelbon said. “I don’t understand their motive behind not wanting to spend money right now because everyone else—especially Toronto and New York—who are in your division, are spending money. To me, it’s going to be fighting between Tampa Bay and the Red Sox for last place in the division.”

The Bregman miss stings even more coming just months after the Red Sox traded Rafael Devers—their highest-paid player—to the San Francisco Giants, with fans expecting that payroll relief to fuel an aggressive push in free agency. Instead, Boston’s final offer to Bregman reportedly came in at $165 million over five years, loaded with deferrals—$10 million short of what the Cubs put on the table without heavy back-loading.

The gap has reignited frustration over the organization’s spending philosophy, with many feeling the club is back at square one despite clearing Devers’ contract.

But Papelbon didn’t just criticize—he offered a clear path forward.

“Now, who are you going to go after? What are you going to do next?” he asked. “To me, they’ve got to get in on the Bo Bichette deal.”

Pursuing Toronto’s star shortstop would be a bold statement. Bichette, expected to command an even larger contract than Bregman’s, would instantly inject elite offense into the Red Sox infield and prove the front office is finally ready to match the financial firepower of division rivals.

For a fanbase already on edge, Papelbon’s message was unmistakable: spend big, or get left behind. The jig is up—Boston’s front office can no longer hide behind deferred money and near-misses. The clock is ticking.