Boston landed Bregman on a three-year deal with opt-outs last winter. They juiced the average annual value to $40MM, albeit with significant deferrals that dropped the actual value closer to $30MM annually. Bregman is no longer attached to a qualifying offer and coming off a better season on a rate basis than he had in 2024. He's also entering his age-32 season, so he may be more incentivized to secure the longest deal and maximum guarantee.
The Blue Jays have completely upgraded their pitching staff from what they had as a starting point last season to what they will have on Opening Day in 2026. Getting Dylan Cease and Cody Ponce were moves that were highly touted, as well as having Shane Bieber exercise his 2026 option. Meantime, the addition of Tyler Rogers to the bullpen address their need to have pitchers who are better at limiting home runs and walks in high leverage situations.
According to a report from Yahoo Japan, infielder Kazuma Okamoto is in the US to meet with teams as he nears the end of his 45-day posting window. He's got less than a week left before his decision is due, so it's safe to assume the pool of suitors is relatively small. The Angels, Blue Jays, Padres, Pirates, and Red Sox have all been strongly connected to Okamoto, with the Cubs and Diamondbacks also being mentioned as possibilities.
With Christmas in the rear view mirror and start of a new week here, it could make sense for some more free agents to find new homes in the coming days. While still in the midst of the holiday season, recent years have shown activity can still be fast and furious. Perhaps the Braves can end 2025 and enter 2026 with their off-season basically complete if they can find a move for a starting pitcher they like this week.
Much of what is reported about specific player connections is done so because either a team or player rep wants to create leverage, and that's never more true than during the Winter Meetings. Whether it's a smoke screen to obscure other pursuits or a way to spur increased offers from interested parties, there's almost always an angle to the information that goes public.