In Major League Baseball, players move on to other teams all the time. It is the business of baseball. Some are traded. Some leave via free agency. Some are traded for a bag of baseballs. Some are traded for a bunch of prospects who cannot throw or hit baseballs. Some are generational talents and are traded away for no logical reason, most notably a player with the initials MB. The Boston Red Sox are an organization that makes trades, executes moves in free agency, and let a player with the initials MB go elsewhere to continue his baseball journeys. It just stings a little more when the Red Sox trades, free agencies, and non-signings don’t actually pan out in their favor. And worse, when their transactions make another MLB organization infinitely stronger.

Since it is MLB Playoff time, I thought it would be fun to construct a fantasy roster of former Boston Red Sox players who are now helping other franchises in this year’s postseason. I wanted to note that the Boston Red Sox did not make the postseason in 2024, but let’s put those emotions aside for this fun exercise. Okay, this list of former Red Sox players will range in emotions from who cares to me needing a box of Kleenex to wipe my tears. Here is my starting roster of position players:

• 1st Base – Kyle Schwarber, an epic and short stint with Boston produced some of the funniest defensive woes and triumphs for “Kyle from Waltham.” Schwarber is now the best DH in the game of baseball after that LAD guy with 50 steals/50 home runs. Boston fans, let’s all say it loud and proud – You are welcome at 1st Base anytime, Kyle!
• 2nd Base – Jose Iglesias, a defensive star with Boston and every single team since he was traded to Detroit for Jake Peavy in 2013. Iglesias has been playing outstanding 2nd base for the Mets this postseason and has held his own at the plate.
• Shortstop – Xander Bogaerts, wow how much time do you have. Bogaerts was a staple in the Red Sox lineup for over a decade. His talents have shifted to the San Diego Padres, who are in a big time battle with the LA Dodgers this postseason. For my money, the X Man should have stayed a Red Sox for life!
• 3rd Base – Kiki Hernandez, a multi positional talent who was equally impressive as a CF as he was at short. Kiki was a dynamic player for Boston before heading back to Los Angeles, where he won a WS in 2020. Kiki is playing significant innings for LAD this postseason in the infield.
• Left Field – Alex Verdugo, this was a sort of shocking trade when Verdugo went to the rival NYY last off season. Verdugo was an up and down player who never really hit his full stride with Boston. Good player, plays just about every day now for the NY Yankees in left field.
• Center Field – Mookie Betts, a generational talent who was let go for the aforementioned Alex Verdugo, Jeter Downs, and Connor Wong in one of the most lopsided trades in MLB history, in my opinion. No offense to the three Boston got, but LAD pulled off a monumental trade without giving up even 1/10000 of Betts value. Betts is my favorite player in MLB right now. He is so talented, offensively, stealing bases, playing multiple positions, wow he is a star player.
• Right Field – Tommie Pham, I always appreciate quality veteran leadership. Veterans that take quality at bats so others can see breaking pitches. Veterans who know how to bunt a runner over. Veterans who play solid defense and don’t make silly throws to the wrong base. Pham’s visit to Boston was short but he was always ready when called upon. Now Pham is helping the KC Royals trying to upset the NY Yankees, so I am a huge Pham fan right now.
• DH – JD Martinez, a crafty hitter with power and a right field gap hitter like few of his peers. JD spend several seasons in Boston as their primary DH and performed at a very high level for most of them. Professional hitters like JD are very much sought after and he is now hitting homers and singles for the NY Mets as they take on their nearly cross state rivals, the PHI Phillies. JD was well liked in Boston, nothing bad to say here.
• Starting P – Chris Sale, even though he was hurt and did not pitch in the postseason for Atlanta, he is still my starter. Sale had a bounce back year, winning the NL Pitching Triple Crown (wins, era, K’s) and will be the odds on favorite for the NL Cy Young Award. His huge Boston salary and lack of time on the mound became a huge splinter in every Sox fan’s side. He had to go, everyone knew it. I’m glad he is healthy and doing well. I just wish we could have had a few more years of this Sale on the Sox, as opposed to the constant DL Sale we got used to.
• Manager – None better than Terry Francona. I like current Manager Alex Cora, but there was something about a Terry Francona team that just made you stand up and cheer. He seemed to get more out of average players and get legendary moments out of great players. His run in Boston was legendary as a manager, culminated by the 2004 run to the World Series and eventual title. Tito, as he is commonly referred to as, will be taking his talents to Cincinnati next season to try and rebuild the woeful Reds.

All these former Boston Red Sox players know the drill. Free agency, trades, DFA’s, unconditional releases – it is all part of the business of baseball. Still, it would have been awesome for the Red Sox to have kept players like Betts and Bogaerts, maybe JD and Sale. The others, I’m okay with them going elsewhere to continue their baseball journeys.

Also, I want to say RIP to Luis Tiant, whose pitching windup and charisma were second to none for generations of baseball fans. My condolences to his family and the millions of baseball fans who enjoyed his character on and off the field for so many baseball seasons.