Red Sox insider’s offseason contract prediction will test John Henry’s limits

The Boston Red Sox organization has caught heat from fans, reporters and former players for its lack of effort in recent offseasons.

Boston's payroll has plummeted since 2018 and it's shown in the product on the field. The Sox have missed the playoffs in five of the last six seasons after securing four championships in 14 years. The sudden change in budget has Red Sox fans wondering when things will be back the way they were from 2004-18. Team owner John Henry has admitted to being afraid of mega-deals, but he has plenty of money to give one — or more — out this offseason.

Boston fans may be in luck this winter. In a recent Q&A session on Reddit, The Boston Globe's Red Sox reporter Alex Speier answered what he thinks could be the largest contract the front office may dish out this offseason.

"The team's urgency is such that I'd expect there to be a $100M+ deal this winter," Speier replied.

Red Sox reporter Alex Speier predicts the front office will offer a '$100 million-plus' contract this offseason

The "urgency" Speier referenced was palpable at the team's end-of-season press conference and soon afterward. Alex Cora, Sam Kennedy and Craig Breslow each used stronger language to describe the aggressiveness of their impending offseason pursuits than last year's promises. Fans are growing restless due to the constant middling records and playoff misses, so they had better deliver.

A $100 million-plus deal could put the Red Sox in play for a few critical pieces to lift them from a .500 record into playoff contention. Boston needs more righty bats, bullpen reinforcements and a true ace to lead its relatively inexperienced pitching staff. The Red Sox also have plenty of talent in their farm system they could trade to meet any of those needs, which would be a nice supplement to a large contract for an ace.

A $100 million-plus contract will be on the low end for some of the winter's most coveted players. Juan Soto's deal is all but certain to be more than $500 million and Corbin Burnes and Max Fried will both be offered significantly more than $100 million by the league's wealthiest owners.

Speier's confidence could be comforting to Sox fans, though. The Red Sox organization started to see the consequences of its neglect of the team when Fenway Park wasn't packed every day and was loaded with away fans. The team's 81-81 record proved they're close to contention, and not spending this offseason would be a waste of their productive 2024.

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