Red Sox Whiff, Dodgers Lose Edwin Díaz, Plus 2 More Moves Aging Poorly

There were a handful of decisions made this past offseason that haven't aged well.

May 15, 2026; Chicago, Illinois, USA; Chicago Cubs third baseman Alex Bregman (3) scores against the Chicago White Sox during the seventh inning at Rate Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

We're now about two months into the 2026 Major League Baseball season. This is a big enough sample size to really judge some of the moves made this past offseason.

Naturally, there were plenty of good moves made. The Toronto Blue Jays went out and signed Dylan Cease to a seven-year, $210 million deal and he has responded with potentially the best season of his career so far. Cease has a 2.98 ERA so far this season in 10 starts to go along with an 84-to-25 strikeout-to-walk ratio in 57 1/3 innings pitched.

Another good move that was made was the Philadelphia Phillies re-signing of Kyle Schwarber to a five-year, $150 million deal. He's leading the league with 20 homers right now and has also driven in 36 runs in 47 games played. There has been a lot of good. But a few moves have backfired.

Boston Red Sox Acquiring Caleb Durbin/Letting Alex Bregman Go

May 14, 2026; Boston, Massachusetts, USA; Boston Red Sox third baseman Caleb Durbin (5) makes a catch for an out against the Philadelphia Phillies during the third inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

A double-whammy right off the bat. The Red Sox whiffed at third base. Boston let Alex Bregman walk in free agency after publicly calling him the club's priority. Things didn't work out in negotiations, though. Now, Bregman is a member of the Chicago Cubs. Durbin has struggled mightily offensively and to make matters worse, the guy the Red Sox gave up — Kyle Harrison — looks like a legit Cy Young Award contender.

Dodgers Signing Edwin Díaz

Mar 27, 2026; Los Angeles, California, USA; Los Angeles Dodgers pitcher Edwin Diaz (3) delivers to the plate as he earns a save in the ninth inning against the Arizona Diamondbacks at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | Jayne Kamin-Oncea-Imagn Images

This deal certainly could take a turn for the better, but so far things haven't been good. Díaz made seven appearances and had a 10.50 ERA before landing on the Injured List and undergoing elbow surgery. There has also been a bit of controversy around him this season.

Orioles Signing Pete Alonso

May 20, 2026; St. Petersburg, Florida, USA; Baltimore Orioles first baseman Pete Alonso (25) hits a home run against the Tampa Bay Rays in the sixth inning at Tropicana Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

Another deal that could turn around for the better, but hasn't been good to start. Alonso has just nine homers in 50 games so far for the Baltimore Orioles and is slashing .228/.310/.434 with a .744 OPS. Last year, he played in 162 games with the New York Mets and hit 38 homers, drove in 126 runs and slashed .272/.347/.524 with an .871 OPS. He certainly hasn't played at that level yet in an Orioles uniform.

Astros Signing Tatsuya Imai

May 18, 2026; Minneapolis, Minnesota, USA; Houston Astros starting pitcher Tatsuya Imai (45) delivers a pitch against the Minnesota Twins in the first inning at Target Field. Mandatory Credit: Jesse Johnson-Imagn Images | Jesse Johnson-Imagn Images

Tatsuya Imai's big league career has gotten off to a rocky start. He has made just five starts and has an 8.31 ERA in 17 1/3 innings pitched. That certainly wasn't the expectation coming in for him or Houston.