I have one decent-sized trade to show off here and it is a very random group of players. Some all-time greats, current players, random players from the past, and some failed prospects. But, that's what I like.
1. Milt Bolling. Bolling was with the Red Sox from 1952 through 1957 and was the team's primary shortstop in 1953 and 1954. He wasn't too bad, but was the standard shortstop for the time period, meaning he was much better defensively than at the plate. For the two seasons, he hit .255/.329/.361 with eleven homers and 63 RBIs. Not great, but not terrible. His defensive numbers were pretty decent though. He was eventually traded to the Senators in a deal for Dean Stone.
2. Donnie Sadler. Sadler was supposed to be the Red Sox starting second-baseman in the late 1990's, pairing with Nomar Garciaparra. He was very fast but he just didn't show enough at the plate to guarantee any kind of regular role in the lineup. He was eventually traded to the Reds in the deal for Chris Stynes.
3. Michael Coleman. Coleman was a top prospect at the same time as Sadler and was even included in the same trade to the Reds. He had a 30 homer season in the minors and was apparently nicknamed "Prime Time", much like Deion Sanders. His attitude cost him a career unfortunately. He was never really given much of a shot in the Majors with 39 plate appearances being his career high. He did not impress in those shots, but still, given his minor league numbers, he should have been given a bigger shot.
4. Tim Wakefield. Wakefield is third all-time in wins in Red Sox history, behind just the tie between Cy Young and Roger Clemens. He had 186 wins for the Red Sox, which has more to do with the length of time he pitched for the Red Sox, his career high was 17 wins (which he accomplished twice). Wakefield holds the team record in games started (430) and innings pitched (3,006). He also holds the team record in several less complimentary stats such as hits allowed, HBPs, earned runs, and losses, none of which is terribly surprising given his lengthy stint with Boston.
5. Hideki Okajima. Okajima is still the only Red Sox middle reliever to make the All Star team. He accomplished that feat in his rookie season of 2007 when he had a 2.22 ERA in 69 innings pitched with 63 strikeouts and 17 walks.
6. Adrian Gonzalez. It's sort of forgotten now, but A-Gon's only full season with the Red Sox was an absolutely amazing season. He hit .338/.410/.548 with 27 homers and 117 RBIs. He was an All Star and won both the Silver Slugger and Gold Glove while finishing seventh in the MVP race. He led the league in hits (213) and also had 45 doubles. It was simply a monster season.
7. Andrew Benintendi. Benintendi has settled into more of an average career, which is sort of disappointing given the start to his career. He finished a distant second in the Rookie of the Year vote to Aaron Judge in 2017. That year, he hit .271/.352/.424 and had a 20/20 season with 90 RBIs.
8. Michael Chavis. Chavis had big-time power, but the strikeouts just killed his career. His best season was still his rookie season in 2019 when he hit .254/.322/.444 with 18 homers and 58 RBIs. But even that year he struck out 127 times in 382 plate appearances.
9. Alex Verdugo. He is just 30 years old, but Verdugo's career appears to be over. He did not appear in a single Major League game in 2026, last appearing with the Braves in 2025. He hit .281/.338/.424 with 43 homers and 206 RBIs in four seasons, including the shortened COVID season. Not bad numbers really, but a far cry from what was hoped for from the main piece acquired for Mookie Betts.
10. Nathan Eovaldi. Eovaldi has had a weird career. For a pitcher who is often considered one of the best in the game, his 15-year career has only yielded a record of 113-94 and 26.4 bWAR. Much of the issue has been due to injuries, he has only twice pitched in 30 or more games and never broken 200 innings pitched.
11. Alex Verdugo.
12. Connor Seabold. Seabold was supposed to be the big get in the trade of Brandon Workman and Heath Hembree to the Phillies in 2020. But Nick Pivetta was significantly better. Seabold only pitched five games in Boston over two seasons, and has since made appearances for the Rays, Braves, Tigers, Blue Jays and Royals.
13. Alex Verdugo.
14. Connor Seabold.
15. J.D. Martinez. It's a shame it took so long for Martinez to get going and that his decline happened so fast. He was an incredible hitter for several seasons. From 2014-2021, he averaged .298/.365/.561 with 30 home runs and 89 RBIs, good for a 144 OPS+. Those are Hall of Fame numbers. Unfortunately, he didn't do as much in the rest of his career and finished with 1,741 hits, 331 homers and 1,071 RBIs. Very good numbers, but not enough for the Hall.
16. Kyle Teel. Boston has been trading first-round picks a LOT lately. Teel, the 2023 first-rounder, was moved to the White Sox, along with 2024 first rounder Braden Montgomery for Garrett Crochet. Nick Yorke (2020), Marcelo Mayer (2021) and Kyson Witherspoon (2025) have also all been traded in the last few years. Former first-rounders still in the Red Sox system include Tanner Houck (2017), Triston Casas (2018), Mikey Romero (2022), Marcus Phillips (2025) and Jake Schaffner (2026).
17. Masataka Yoshida. Yoshida's OPS+ of 109 during his four seasons in Boston is not really that bad, it just isn't quite what the team hoped for, and the fact that he has missed significant amounts of time in the last three seasons due to injuries is a big part of the reason why his time in Boston is likely coming to an end. The team needs to improve at the designated hitter position, and I could see his release coming. It's unfortunate. When he's on, he can really hit.
18. Jim Rice. Rice was Boston's first first-rounder to make the Hall of Fame. He was selected in the 1971 draft 15th overall.
19. Rafael Devers. I am still extremely disappointed we will not see Devers's entire career with the Red Sox as we were supposed to. I believe he is on a Hall of Fame trajectory, though that is complicated by his move to first base. Still, he has 272 career home runs and is just now 30. He has an outside shot at 500.
20. Nick Sogard. Sogard turned into a dependable second-baseman, if not a flashy one. He is a decent player, but probably not a starter on a contending team. There's not a ton of upside in his game, but he is a very good bench player.
21. Alex Bregman. After a slow start to his first season with the Cubs, Bregman turned his season around and turned in the kind of season the Red Sox had hoped he would have for them. But he dealt with a lot of injuries in his only year in Boston. An interesting note is that Bregman was actually originally drafted by the Red Sox in the 29th round in 2012, but did not sign at the time.











