Regrading 10 of the Biggest MLB Trades From Last Year

Deadline deals in Major League Baseball season are coming in hot before the buzzer Monday night. 

Let's pause to review 10 of the biggest trades from a year ago and see how they grade out right now for both sides.

1. RHP Mason Miller and LHP JP Sears (Athletics) for SS Leo De Vries, RHP Braden Nett, RHP Henry Baez and RHP Eduarniel Nuñez (Padres)

MLB enthusiasts will be talking about this one for a long time. Miller has been the best reliever in the league, and only one other prospect currently ranks higher overall than De Vries, who isn't even 20 years old yet.

Padres president A.J. Preller gambled that dealing De Vries for Miller would help his team win the World Series. It hasn't happened yet and might not ever, but the Padres did make the playoffs in '25 and are close to a postseason spot again. Miller isn’t a free agent until 2030, and he still could be a starting pitcher someday, throwing 102 mph. There’s also a chance the Padres trade him, though finding the right kind of return will be tricky.

With De Vries in Class AA, the A's are in fine shape to bring him up next season and possibly contend in an open AL West.

Grades

Padres: B. Athletics: A.

2. RHP Jhoan Duran (Twins) for C Eduardo Tait and RHP Mick Abel (Phillies)

Duran has been nails for the Phillies, and is a key part of them contending for the World Series. He won't be a free agent until 2028.

Analysts differ in their rankings on Tait, but as a 19-year-old catcher with a .440-something slugging percentage in High-A, the Twins will be patient the next two years while he develops. Abel has shown flashes with the Twins in the majors but was shut down after arthroscopic surgery on his elbow.

Grades

Phillies: A. Twins: B-.

3. RHP David Bednar (Pirates) for C Rafael Flores, C Edgleen Perez and OF Brian Sanchez (Yankees)

Bednar has been terrific at the back end of the Yankees bullpen, perhaps one of the 10-12 best relievers in the league. He'll be a free agent this winter. The Bucs, now fringe contenders for the postseason, could use a pitcher like him at the end of games. Oh, the irony.

Perez showed a lot of improvement at the plate in the low minors, and Flores is getting back-up time in the majors right now. Sanchez could jump into the Pirates' top 30 prospects next season.

Grades

Yankees: A. Pirates: B-.

4. 1B Josh Naylor (Diamondbacks) for LHP Brandyn Garcia and RHP Ashton Izzi.

Naylor was a key part of Seattle's postseason run in 2025, and they re-signed him in free agency over the winter. He's been banged up and less effective this season, and the M's are barely hanging onto their playoff hopes.

Garcia has been a terrific addition to Arizona's bullpen and has a chance to pitch in the postseason. Izzi just got promoted to Triple-A.

Grades

Mariners: A. D-backs: A

5. SS Carlos Correa and cash (Twins) for LHP Matt Mikulski (Astros)

Moving to third base, Correa hit well for the Astros at the end of '25 but they failed to make the playoffs. He again hit well at the start of '26 but sustained a significant ankle injury in May that has sidelined him ever since. The Astros still have a chance to make the playoffs without him.

The Twins will have sent $33 million to the Astros by the end of 2028 to help pay Correa's salary. They released Mikulski in October.

Grades

Twins: D. Astros: B.

6. RHP Shane Bieber (Guardians) for RHP Khal Stephen (Blue Jays)

Bieber pitched well in seven starts to help the Blue Jays reach the World Series in ‘25. He's only made seven starts this season after recovering from injuries, and only two of his appearances have been effective.

Stephen pitched well in Double-A at age 23, but he just had Tommy John surgery in July.

Grades

Blue Jays: A. Guardians: C.

7. RHP Griffin Jax (Twins) for RHP Taj Bradley (Rays)

This deal didn't really form up until this season, after the Rays converted Jax back into a starting pitcher, and Bradley started to shove for the Twins. Some of the superficial numbers are close by comparison, but Bradley looks like the better long-term starter. He’s also about five years younger, and is not a free agent until 2030.

Grades

Rays: B-. Twins: A-.

8. SS José Caballero (Rays) for OF Everson Pereira (Yankees)

Caballero's offense has regressed to the mean (about 15% below league average) this season, but he's also been one of the better defensive players in the league at a premium position. The Rays traded Pereira in November for RHP Yoendrys Gomez, whose contract they later sold to the Twins.

Grades

Rays: D. Yankees: B.

9. RHP Louis Varland and 1B Ty France (Twins) for OF Alan Roden and LHP Kendry Rojas (Blue Jays).

Varland helped the Jays reach the World Series in '25. He transformed this season into perhaps the best reliever in the league after Mason Miller. He's not a free agent until 2031.

Roden has been injured most of this season and hasn't performed well in 17 games. Rojas, who turns 24 in November, has looked like a great prospect in five appearances.

Grades

Jays: A. Twins: C.

10. RHP Dustin May (Dodgers) for OF James Tibbs III and Zach Ehrhard (Red Sox)

May didn't help Boston's playoff push much and was sidelined with elbow soreness for the AL Wild Card series. He signed a one-year contract with the Cardinals in free agency, and has had a strong 21 starts, setting up another possible deadline move to a better contender.

Tibbs (24 years old in November) and Ehrhard (24 in January) continued to develop as strong-hitting outfielders at Triple-A, and help to give the Dodgers unrivaled organizational depth.

Grades

Red Sox: D. Dodgers: A.