There are multiple reports that Kyle Schwarber‘s decision on where he is going to play the rest of his career is going to come sooner rather than later. At first, the date to circle was Christmas, but now word is that he would like to wrap up the process before the Winter Meetings begin on Sunday. At the latest, he wants to make it official during the meetings in Orlando.
There are a lot of suitors for his services. Some teams need him more than others and some teams just make more sense than others. One surprise team that seemed interested early on has been the Pittsburgh Pirates and they haven’t backed off of the thought of signing him or at least making a strong bid. While it would be unheard of for Pittsburgh to throw around the money Schwarber is going to get, it makes sense. Consider a couple of things: Pittsburgh has a number of good, young players either in the majors or very close to being in the majors. Paul Skenes is at the head of that class and there have already been rumors that he wants out of Pittsburgh because they can’t win. What if the Pirates were to go for it? They have the money, they have just chosen not to spend it. They also have a short right field porch that would have a huge bullseye on it every time Schwarber looked out there.
Another issue is the upcoming labor agreement. It’s very possible that the player’s association will push for a salary floor to make low spending teams like the Pirates give out more money to players. The Pirates may want to get ahead of that.
From Schwarber’s side though, it would be very risky. He would instantly make them better, but not good enough to truly contend until some of the younger players hit their stride. Don’t look for Pittsburgh to win the bidding, but losing gets old and maybe they’ll look to build on the young players coming along.
Baltimore has also been mentioned. The Orioles fell backwards last season, but they won 91 games in 2024 and still have some good players. Schwarber would have a lot of fun hitting in that park and the Orioles would pull themselves back up in the AL East standings with a bat like Schwarber’s in the lineup.
Steve Cohen doesn’t know what to do with all of his money in New York, so he just keeps shoveling it out. The Phillies and Mets rivalry gets hotter than ever before if Schwarbombs were being launched from a New York Mets uniform. Plus, if the Mets can’t re-sign Pete Alonso, they have their replacement and can move Mark Vientos to first base full-time.
Now onto the real contenders
Cincinnati is intriguing. They had a playoff team in 2025 and much of their lineup is still young and developing. Schwarber in the lineup with Elly De La Cruz is an intriguing. The Reds have one thing that the other bidders don’t have and can’t get. Schwarber is from Middletown, Ohio, a little under 40 miles outside of Cincinnati. Schwarber would be sleeping in his own bed, have a talented lineup around him, and be playing for Terry Francona, who is the ultimate player’s manager.
The Red Sox also have something to entice Schwarber; Fenway Park. Schwarber has great numbers at Fenway – 26 G, 6 HR, 15 RBI, .344/.478/.644/1.122 – and he was a fan favorite in the short time he played there late in the 2021 season.
Schwarber developed a real love for Philadelphia in his four seasons with the Phillies. The fans love him and WAWA named a drink after him; what more can a player ask for? For those outside of Philly, WAWA is a regional convenience store chain that had a drink called a Schwarbomb.
It’s been thought all along that Schwarber would re-sign with the Phillies if they were willing to give him the money and years that he wants. None of the alternatives – Pete Alonso, Kyle Tucker, Cody Bellinger – have the appeal to the Phillies that Schwarber does. Schwarber becoming a free agent may have been one of those exercises where a player goes out to see what he can get, brings the top offer back to a team and says “match this.” It’s likely that the Phillies do match it and Schwarber is back in the fold not just because of what he can do on the field, but because of what he brings to the clubhouse.
If Schwarber does sign soon, that opens up the flood gates. From a fan’s standpoint, it would be great to come prior to the Winter Meetings because the meetings have become somewhat sluggish over the past number of years. It used to be one deal after another going down, but now, the signings drag out into late winter and sometimes into the spring. Remember, it was March until Bryce Harper signed.
Not only would it open things up for other players, it would open things up for the Phillies. They would know where they stand financially and could go full speed ahead to find fits for their outfield and bullpen. We can only hope that a deal is done sooner rather than later.
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