There are always going to be movement of players in sports. Whether it be from trades or free agency, teams are going to have different rosters throughout the years. However, there have been some incredible regrets from general managers over the years seeing players that wore their jerseys now dominating somewhere else.
Because it would be interesting, all these players are currently on a MLB roster. Let’s look at each MLB team’s biggest regret from moving on from.
Arizona Diamondbacks: Paul Goldschmidt
The Diamondbacks gave away All-Star first baseman Paul Goldschmidt to the Cardinals for Luke Weaver, Carson Kelly and Andy Young. Arizona did not want to pay him as he was approaching free agency and shipped him away. He has been a dominant force in the middle of the St. Louis lineup ever since the move.
Atlanta Braves: Freddie Freeman
The Atlanta Braves have been doing extremely well at getting young players and locking them into long contracts. However, Freddie Freeman was not one of them as he left after the 2021 season. The team did replace him with Oakland’s Matt Olson, more on him later, but the loss of a developed talent definitely stung a little.
Baltimore Orioles: Manny Machado
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When the Baltimore Orioles traded away Manny Machado, they knew they were going to not be happy as he was going to be a free agent at the end of the year and not pay him to stay. They shipped him to the Dodgers and he signed the following offseason as the first piece to the San Diego Padres rebuild. He has continued to play extremely well and would’ve been a strong veteran for the young crop of Orioles to lean on.
Boston Red Sox: Mookie Betts
While the Boston Red Sox wanted to trade away the David Price contract, they attached Mookie Betts to the deal. Boston got back Jeter Downs (now with Washington), Connor Wong and Alex Verdugo. That does not seem equal in value to a potential NL MVP candidate for the next decade.
Chicago Cubs: Gleyber Torres
When the Chicago Cubs traded then-prospect Gleyber Torres to the New York Yankees for closer Aroldis Chapman, they knew it would hurt in the future. Torres was considered a star in the making and has a career .788 OPS with 121 home runs at 26 years old. The trade did help the Cubs win the World Series so it did work out at the time.
Chicago White Sox: Fernando Tatis Jr
Fernando Tatis Jr was once a prospect traded in the James Shields deal. Tatis has become a star at just 24 years old that has dominated with a .910 career OPS and 147 OPS+ for the San Diego Padres. He is going to continue dominating with a massive contract and already a pair of Silver Sluggers in his trophy case.
Cincinnati Reds: Sonny Gray
The Cincinnati Reds traded Sonny Gray to the Minnesota Twins for prospect Chase Petty. Gray was an All-Star this season and is leading the American League in ERA as of this writing with less than a month to go in the season. Having an ace like that would help this young Reds team.
Colorado Rockies: Nolan Arenado
When Nolan Arenado was traded to the St. Louis Cardinals, there was a lot of questions by fans. The Rockies decided to also pay a portion of the contract in the deal as well for their best player and in 434 games, he has a .890 OPS with two Gold Gloves, three All-Star appearances and finished third in the NL MVP voting last season. Not good to trade that talent away.
Detroit Tigers: Eugenio Suarez
In December 2014, the Detroit Tigers traded away pitcher Jonathon Crawford and third baseman Eugenio Suarez to the Cincinnati Reds for pitcher Alfredo Simon. Suarez has become a solid hitter and almost has a 20 career Baseball Reference WAR and helping the Seattle Mariners now make a push for the postseason while Detroit is trying to get any lick of offense.
Houston Astros: Gerrit Cole
While this is something we will touch upon later, losing Gerrit Cole was tough for the team. They had solid pitchers but Gerrit Cole leaving as a free agent and joining the Yankees was tough for some fans. Cole allowed six runs in 36.2 innings during their 2019 postseason run and that was a tough loss that they eventually got over.
Kansas City Royals: Whit Merrifield
During the 2022 MLB Trade Deadline, Whit Merrifield was sent to the Blue Jays for Samad Taylor and Max Castillo. Since being traded, He has been a similar hitter with an All-Star appearance in 1.5 seasons thus far. As a more experienced player leading this younger Toronto roster, this is a great role that he would’ve been with Kansas City. .
Los Angeles Angels: Kyle Bradish
One weakness for the Angels in the recent decade has been the inability to have solid pitching. However they traded away one of the better young pitchers in Kyle Braish to acquire Dylan Bundy in December 2019. That definitely did not help things for the team and now is in contention for the AL Cy Young Award less than four years later for the Orioles.
Los Angeles Dodgers: Yordan Alvarez
Yordan Alvarez with this Dodgers lineup almost happened but they traded him for reliever Josh Fields at the 2016 MLB Trade Deadline. That one has to hurt knowing another star in their system could be shining in the middle of this incredible lineup.
Miami Marlins: Miguel Cabrera
Cabrea was traded in December 2007 to the Detroit Tigers alongside Dontrelle Willis to the Detroit Tigers and that significantly hurt the franchise. Cabrera went to become Mr. Tiger since being traded and is set to retire after the 2023 season. He won two AL MVPs, a Triple Crown, four batting titles and seven Silver Sluggers.
Milwaukee Brewers: Josh Hader
Closer Josh Hader spent his first 5.5 seasons with the Milwuakee Brrewers before being traded at the 2022 Trade Deadline to the San Diego Padres. The trade made the Brew Crew drop out of contention last year and severely hurt the locker room.
Minnesota Twins: Yennier Cano
Having a dominant reliever really helps put a team in contention and that happened when the Twins traded away Yennier Cano to the Baltimore Orioles. He had a 9.22 ERA in 10 games with the Twins but made the All-Star team and has a 2.66 ERA and has been incredible for the Orioles.
New York Mets: Marcus Stroman
While not being in the Big Apple for long, it was apparent Marcus Stroman wanted to pitch in his home state. After being told he was going to the Yankees, the Mets swooped in and traded for him during the 2019 Trade Deadline from the Toronto Blue Jays. He would pitch two seasons as he sat out the 2020 COVID year before becoming a free agent and signing with the Chicago Cubs. He was an All-Star in 2023 and considered for the NL Cy Young before being injured. The pitching woes in the Mets would have been helped with Stroman on the bump.
New York Yankees: Jordan Montgomery
While the problem with the Yankees in 2023 has not been their pitching, it still hurts to see him in a different uniform. Montgomery has not been dominant but when he was traded at the 2022 MLB Trade Deadline for an injured Harrison Bader, questions arose. It made no sense then and now with Harrison Bader off the team and now with Cincinnati as a waiver claim, this move still hurts as Montgomery would have help an injury-ravished Yankees rotation.
Oakland Athletics: Matt Olson
While some may argue that Matt Chapman should be here, the Athletics had a solid first baseman in Matt Olson. He established himself as a solid first baseman made a pair of All-Star teams in the AL but was traded to the Atlanta Braves before the 2022 season. Oakland received Shea Langeliers, Cristian Pache, Ryan Cusick and Joey Estes, which are not the talent that Olson has shown to be.
Philadelphia Phillies: Zach Eflin
Zach Eflin pitched the first seven years of his big league career with the Philadelphia Phillies before becoming a free agent in the 2022 offseason. He was 36-45 with a 4.49 ERA in the City of Brotherly Love but signed with the Tampa Bay Rays. He currently s 13-8 with a 3.40 ERA in 26 starts and is approaching his most innings in a season while leading baseball with a 1.022 WHIP. That one stings a little bit.
Pittsburgh Pirates: Gerrit Cole
The Pittsburgh Pirates knew they had a star in Gerrit Cole when they drafted him first overall in the 2011 MLB draft. However, they moved him during the offseason before the 2018 season to the reigning champion Houston Astros. Pittsburgh received Colin Moran, Jason Martin, Joe Musgrove and Michael Feliz. That is not what Gerrit Cole should net a franchise.
San Diego Padres: Corey Kluber
At the 2010 Trade Deadline, the Padres had a three-team deal in place with the Cardinals and then-Indians where they traded away essentially a non-prospect Corey Kluber to Cleveland to get some offensive help. What happened is that Kluber would become a two-time Cy Young winner and dominant on the mound.
San Francisco Giants: Kevin Gausman
In a season where they have not had many starting pitchers, Kevin Gausman would have been a help to eat innings at worst. In his two seasons since leaving the Giants and being with the Blue Jaus, he is 22-18 with a 3.33 ERA and an 11.1 strikeouts per walk in 330 innings. He was ninth in the 2022 AL Cy Young voting and a 2023 All-Star.
Seattle Mariners: Edwin Diaz
The Edwin Diaz trade during the 2018 offseason was something very interesting for the Mariners. They traded away their closer who led baseball with 57 saves and had AL MVP votes. The full trade was Edwin Diaz, Robinson Cano and $20 million for Jay Bruce, Anthony Swarzak, Jarred Kelenic, Justin Dunn and Gerson Bautista. Dunn is now with the Cincinnati Reds while Kelenic has a 0.1 Baseball Reference WAR and an 84 OPS+. Diaz had an electric 2022 season with a 1.31 ERA and 32 saves and should return to dominance next season.
St. Louis Cardinals: Sandy Alcantara
Prospect trades are tough but the St. Louis Cardinals were getting All-Star outfielder Marcell Ozuna and had to get rid of some prospects. One of them was Zac Gallen and the other is Sandy Alcantara. Alcantara pitched eight gams in 2017 for the team and had a 4.32 ERA out of the bullpen but now is a perennial Cy Young Award candidate who won the award in 2022.
Tampa Bay Rays: Evan Longoria
The franchise star and captain Evan Longoria was traded away in the 2017 offseason to the San Francisco Giants for a bunch of middling players. While the Rays did not get much back that is still on the team, this one definitely hurt.
Texas Rangers: Yu Darvish
Yu Darvish signed with the Rangers out of Japan in 2012 and pitched well but was traded to the Los Angeles Dodgers during the 2017 season. SInce the 2018 season, Darvish has a 3.77 ERA and has been doing extremely well as he was top-10 in Cy Young votes in two years. That pitching would help Texas now.
Toronto Blue Jays: Rowdy Tellez
Rowdy Tellez has been a good hitter in his MLB career and played for the team from 2019 until bing traded during the 2021 season to Milwaukee. The trade involved Trevor Richards and Bowden Francis to Toronto but that does not help the team compared to Tellez’s ability to rake. That hurts but the Blue Jays were able to rebound off that happening.
Washington Nationals: Juan Soto
It is hard to establish which star to put here as it was between Soto and Bryce Harper. Soto has been doing well in San Diego since being moved at the 2022 MLB Trade Deadline and has done everything incredibly well. Expect the Nationals to look at this trade as something they would want to have back as the years go on.
