About the Off-Season: Compounding Blunders

About the Off-Season: Compounding Blunders

By Tim Kabel

February 10, 2026

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Last year, the Yankees acquired Devin Williams from the Milwaukee Brewers. He was considered to be one of the best relief pitchers in the game, if not the best. He was also on an expiring contract and was set to become a free agent after the 2025 season. The Yankees sent Caleb Durbin, Nestor Cortes, and cash to the Brewers in exchange for Williams.

Williams did not exactly set the world on fire with the Yankees. He struggled throughout the season. There were stretches where he was very good. There were also streaks where he looked like a batting practice pitcher. He did not seem to enjoy his time in New York very much which is ironic, since he signed a contract with the Mets in the offseason. 

Nestor Cortes was ultimately traded from the Brewers to the Padres and then was injured.  He is currently recovering from elbow surgery.

Caleb Durbin, who is 25, played in 136 games for the Brewers last year. He batted.256 with 11 home runs and 53 RBI. He also stole 18 bases. He finished third in the National League Rookie of the Year voting. It could be argued very easily that the Brewers received the best player in the trade. Durbin had a much better year than Williams.

Durbin is a right-handed batter who primarily played third base for the Milwaukee Brewers in 2025. He also played games at second base and shortstop. Many people, me included, advocated for the Yankees to bring Durban to the Major Leagues in 2025. Instead, they traded him to the Brewers.

It would be fair to say that it wasn't a good trade for the Yankees. They received a relief pitcher who underperformed and then became a free agent and left. The Brewers received a pitcher they traded for other assets and a young infielder who finished third in the Rookie of the Year voting.

It gets better. The Yankees presumably wanted DJ LeMahieu to play third base. We all saw what happened with that. Then Oswaldo Cabrera was playing the position, but he suffered a terrible injury and was lost for the season. Oswald Peraza was given a shot but that didn't work out. So, the Yankees made a trade for Ryan McMahon of the Colorado Rockies. The Yankee sent Griffin Herring and Josh Grosz to the Colorado Rockies in exchange for McMahon. 

Ryan McMahon played 54 games for the Yankees. He batted .208 with 4 home runs and 18 RBI. He stole one base. McMahon is 31 years old and is under contract to the Yankees for the next two years. He will earn $16,000,000 in each 2026 and 2027. McMahon is a left-handed hitter.

So, let's recap. The Yankee sent Caleb Durbin, Nestor Cortes, and cash, which they don't like to give up, to the Brewers in exchange for Devin Williams who did not have a great year with the Yankees. Devin Williams left as a free agent. Caleb Durbin excelled with the Brewers. Not only did Durbin excel, but he also played a position where the Yankees had a significant need and wound up sending two ranked pitching prospects to the Colorado Rockies for McMahon to play that position. On the face of it, Durbin would seem to be a better fit for the Yankees than McMahon because he is younger, he hit for a significantly higher average and is a right-handed hitter. The Yankees have repeatedly said that they want more right-handed hitters.

The trade for Devin Williams could be considered a blunder based on the outcome. When you factor in that the Yankees then had to make a trade for Ryan McMahon, who is not an ideal player for the Yankees, the blunder was compounded.

It gets better.

Yesterday, the Brewers traded Caleb Durbin and fellow infielders, Andruw Monasterio, and Anthony Siegler (who is also a former Yankee) to the Red Sox in exchange for left-handed pitchers Kyle Harrison and Shane Drohan, and infielder David Hamilton. The Red Sox really did not give up a lot. Durbin will probably be the starting third baseman in Boston to replace Alex Bregman.

So, not only do the Yankees not have Caleb Durbin, but he is now playing for one of their arch-rivals. He will undoubtedly come back to haunt the Yankees during the season. The blunder has been compounded exponentially.

The Yankees want to cut salary. They want to become more right-handed in the lineup. The series of blunders involving Caleb Durbin resulted in the Yankees paying significantly more for Ryan McMahon, who is not a very good offensive player and bats left-handed, which the Yankees don't want.

If the Yankees had kept Durbin and not traded for Williams or traded someone else for Williams, they would have their answer at third base for significantly less money. That money could have been used to sign another free agent. They would also still have the two pitching prospects they sent to the Rockies for McMahon.

Many people feel the state of the Yankees is not very good right now. The series of blunders they executed in the handling of Caleb Durbin is evidence to prove that point. The bright side is that Durbin will only be with the Red Sox for five years.