If these two All-Stars are going to wait for the Red Sox to step up and give them both the contracts they deserve, they may be waiting a while.
On Monday, ESPN’s Jeff Passan took to his account on Threads to post a thread (no pun intended) of things he’s keeping an eye on as the calendar turns to December.
Here’s how Passan began the thread:
“The calendar turns from November to December in a few hours, and baseball’s hot stove is primed to heat up. As the Winter Meetings start in Orlando a week from today, here are 10 things I’m keeping an eye on.”
Hidden within that thread of 10 items were multiple nuggets about the hot stove season for the Boston Red Sox. Let’s focus on item No. 4:
“Alex Bregman and Pete Alonso: Both were free agents last winter. Both produced well. Both opted out of deals that didn’t reach expectations. And now both are faced with trying to get contracts that better align with their numbers. With the number of teams seeking a middle-of-the-order bat, the chances are good, though both are waiting for a team to step to the forefront.”
Projected contracts for Alonso vary, with reported ranges for a long-term deal going between $150 million and $210 million over five to seven years. Projections range from a five-year, $150 million deal to a seven-year, $210 million contract, with some sources seeing him get closer to $110 million over four years.
Projected contracts for Bregman vary as well, but most reports expect a deal in the range of five to six years and $150 million to $180 million. Specific projections include a five-year, $160 million deal from ESPN, a six-year, $171 million projection from The Athletic, and a six-year, $180 million projection from Baseball America. The final terms will depend on Bregman's preference for length versus average annual value, which is ultimately why the two-time World Series champion opted out of his three-year deal with the Red Sox earlier this offseason.
Both Alonso and Bregman have been linked to Boston since the moment the Red Sox stopped playing baseball this season. Alonso's connection arises from the team's clear need for a power bat in the middle of their order. Bregman's link, meanwhile, is based on what he contributed to the Red Sox during the 2025 season, both on the field and in the clubhouse.
And while the expectations of both fans and media previously were that Boston would be looking to sign a couple of big pieces to bolster their offense, reporting over the last 24 hours may have just changed that tune for Red Sox Nation.
MassLive’s Sean McAdam reported Sunday that ownership is concerned about exceeding the $244 million Competitive Balance Tax threshold in 2026, as this could trigger financial penalties and other operational restrictions.
According to the report, team officials believe crossing that line would result in a “moderate financial loss.” Because MLB teams do not share their financial records, it’s impossible to verify whether that claim reflects actual revenue projections or an internal preference for maintaining a certain level of spending discipline.
Anyone with a brain can tell you that it’s almost certainly the latter.
What can be evaluated, however, is where the Red Sox currently stand.
MLB Trade Rumors’ Nick Deeds projects Boston’s luxury-tax payroll at around $223 million. This puts the Red Sox about $22 million below the first Competitive Balance Tax (CBT) threshold and $41 million below the second.
If ownership limits payroll below the CBT threshold, Boston’s $22 million cushion effectively sets its offseason spending limit, emphasizing that financial restraint will drive decisions.
And that’s where the situation tightens.
Fans hoping for the Red Sox to sign two marquee hitters like Bregman and Alonso should adjust their expectations.
With both players projected to command well above $20 million annually, Boston will likely find it very difficult to land both and still stay within the spending boundaries described in McAdam’s report.
So if both players are waiting for a team to step up, they may be waiting quite a while for Boston to be the ones to do so.
Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.