The New York Yankees' 6 Worst Trades of Brian Cashman Era

The last time the Yankees traded away a Hall of Famer was Randy Johnson in Jan. 2007. After getting two seasons of an aging Johnson, the Yankees simply sent the "Big Unit" back to Arizona two days shy of the two-year anniversary of originally acquiring Johnson.

It's hard to classify the two transactions involving Johnson as poor trades. Johnson gave a pair of playoff teams 34 victories, and considering the fact that the 2007 Yankees saw 14 pitchers get at least one start, it's plausible to think Johnson could have been used except for the fact that injuries kept him to 10 starts in his return to Arizona.

Still, there are some bad ones in the Brian Cashman era, though mostly because the moves did work out as expected.

Josh Donaldson acquired from Minnesota Twins in 2022

When the Yankees returned for spring training following a lockout by owners, their first major move was acquiring Donaldson from the Twins to supposedly give them some kind of hard edge they felt was missing during the tedious 2021 season.

This is one of those moves that was made several years too late. The Yankees were familiar with Donaldson from his 2015 MVP season for the Blue Jays but the version they received struggled in his age-36 season, hitting .222 with 15 homers and 62 RBIs.

While the Yankees raced out to a 1998-esque start and won 99 games, Donaldson's offense was on the decline and also featured a controversy with former Chicago White Sox shortstop Tim Anderson.

To get Donaldson, the Yankees gave up Gio Urshela, who was an unlikely key contributor to the 2019 team, and Gary Sanchez. After 2021, it seemed like the Yankees had run their course with Sanchez, who was hardly the hitter who hit 20 homers in the final two months of the 2016 season.

This is a bad trade because of what Donaldson gave them, but hardly a bad trade for what the Yankees gave up, since Sanchez has bounced around into a journeyman catcher since being traded

The best part of this trade was the fact that Kiner-Falefa's versatility resulted in him appearing in six positions during the disastrous 2023 season.

Acquiring Jeff Weaver in 2002 leads to Kevin Brown in 2004

Weaver was a promising young pitcher for some struggling Detroit teams, and when the Yankees acquired him in a three-team trade with the A's on July 5, 2002, they were getting someone who was 39-51 but whose record was expected to improve on a team like the Yankees.

Weaver never worked out, going a combined 12-12 with a 5.35 ERA in 47 outings for the Yankees. The last pitch he threw for the Yankees resulted in Alex Gonzalez homering in the 12th inning to win Game 4 of the 2003 World Series for the Marlins.

About a month later, he was traded to the Dodgers for an aging Kevin Brown, who was coming off an All-Star season of 14-9 with a 2.39 ERA. Brown's age-39 season began with him winning nine of 10 decisions, but also an ERA of around 4.

After getting annoyed following an outing against the Orioles, Brown famously broke his hand punching a clubhouse wall. When he returned, the Yankees used him twice in the infamous 2004 ALCS, and "he earned a playoff share" from the Red Sox for getting bombed in Game 7 to complete the historic collapse.

As for who the Yankees gave up to get Weaver, it was Ted Lilly, who won 130 games. Lilly was one of those young starters at the time who the Yankees were unsure of and he truly did not emerge into something dependable until the A's traded him to Toronto in Nov. 2003.

Frankie Montas from the A's in 2022

The Yankees felt they needed an upgrade for the rotation, and Montas was their main target. The only problem was shortly after pitching well against the Yankees in June, Montas left a start early due to right shoulder inflammation that diminished his velocity.

It was an injury that seemingly impacted Montas going 1-3 with a 6.35 ERA in eight starts and led him to not appearing until the final week of the 2023 season.

After splitting 2024 with Cincinnati and Milwaukee, the Mets decided to sign him and are now paying him $17 million for a no-show baseball job of not pitching while rehabbing an injury.

In terms of what the Yankees gave up, JP Sears is the biggest name. He won 11 games for the A's in 2024, was sent to San Diego as part of last July's Mason Miller deal and is in Triple-A.

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Joey Gallo from the Rangers in 2001

In the middle of 2021, the criticism of the Yankees was that they were too right-handed. They attempted to rectify it by acquiring Anthony Rizzo from the Cubs, and that move mostly worked out.

They also attempted to become a little more left-handed by acquiring Gallo from the Rangers. It was not a bad move at the time since despite his .225 average, Gallo hit 25 homers for the Rangers and the Yankees figured they could accept the low average if the power exists.

Gallo gave the Yankees 13 homers in 2021 but also an unsightly .160 average along with 88 strikeouts in 228 plate appearances. In 2022, Gallo was equally as ineffective and at the deadline, the Yankees pulled the plug by sending him to the Dodgers, who also saw similar showings.

To get Gallo, the Yankees gave up five players. Of those players, Ezequiel Duran and Josh Smith contributed to the Rangers winning the World Series in 2023, though they might not have had a spot on the Yankees.

2017 Sonny Gray from the A's

Because of his massive struggles in the regular season and recent comments about never wanting to be a Yankee, it gets forgotten that Gray pitched well enough to give the Yankees a chance at winning Game 3 of the ALCS against Houston in the late innings.

The playoff outing may have been the high point of Gray's tenure in the Bronx. He was 15-16 with a 4.51 ERA in 41 appearances for the Yankees, who pulled him from the rotation after the right-hander allowed seven runs in 2 2/3 innings of a loss to the Orioles on Aug. 1, 2018.

Shortly after the Yankees were eliminated by the Red Sox in the ALDS, GM Brian Cashman openly admitted he was going to trade Gray. Gray is on his fourth team since leaving the Yankees and has a pair of All-Star appearances.

The deal did not work out but it was not catastrophic in terms of the return of Dustin Fowler, James Karprelian and Jorge Mateo. Of those players only Mateo is still active and never played for the A's.

2004 Esteban Loaiza from the White Sox

At the 2004 trade deadline, Esteban Loaiza was coming off being the AL starter for the All-Star game in 2003 as a 21-game winner. The follow up was not All-Star-esque as Loaiza was 9-5 with a 4.86 ERA for the White Sox.

At the same time, the Yankees were uncertain if Jose Contreras would ever work out. Signing Contreras led former Red Sox president Larry Luchino to refer to the Yankees as "The Evil Empire" but in his final two starts ahead of the deal, Contreras was bombed for 15 runs.

Loaiza posted an unsightly 8.50 ERA for the Yankees and contributed to the collapse in the ALCS by allowing David Ortiz's game-ending single in the 14th in Game 5.

Loaiza bounced around for the next few years after leaving the Yankees but never hit his All-Star level and then was involved in some shady things after baseball ended.

As for Contreras, he enjoyed six mostly solid seasons for the White Sox, winning 15 games the following season and three more in the postseason when the White Sox won the World Series.

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