It’s not very often that selling looks like an option for the Yankees at the trade deadline.
But the 2023 Yankees are not like most of The Bronx Bombers — the last-place team is 55-50 and barely keeping its head above water in a brutal AL East gauntlet.
Last season, the Yankees made a series of deals at the deadline, acquiring Harrison Bader, whose postseason heroics made the trade worth it, as well as dealing for Frankie Montas, Scott Effross, Andrew Benintendi and Lou Trivino, which brought uneven success.
As the Yankees look out on a trade deadline of uncertainty, it’s a perfect time to consider all the things they shouldn’t do.
Here are the worst Yankees trades of all time:
A Footnote Becomes a Regret: Willie McGee
During Game 2 of the 1981 World Series against the Dodgers, the Yankees completed a trade that seemed awfully insignificant at the time.
The Yankees sent minor-league outfielder Willie McGee to the Cardinals for pitcher Bob Sykes, who had mostly transitioned to a reliever at that stage of his career.
The deal was an instant catastrophe.
After the Yankees lost the 1981 Fall Classic, McGee helped lead the Cardinals to the next season’s World Series as a rookie, hitting .296 with 24 stolen bases his first year in the big leagues.
McGee then added two home runs and a game-saving catch in Game 3 of the 1982 World Series, as the Cardinals went on to win the championship in seven games.
The righty-hitting outfielder then authored a remarkable career, reaching four All-Star games and winning the MVP in 1985 after he won the batting title with a .353 average and swiped 56 bags.
Sykes, on the other hand, was sent to the minor leagues with shoulder issues, never to play for the Yankees.
Rookie Mistake: Fred McGriff to the Blue Jays
It’s always hard to tell if your prospects are going to pan out — especially if they’re just 18 years old.
On Dec. 9, 1982, the Yankees traded a teenager named Fred McGriff, who had just completed his second season in rookie ball, for reliever Dale Murray and designated hitting prospect Tom Dodd.
Clearly, the Yankees didn’t know what McGriff, who had just posted an. 870 OPS in rookie ball, was going to become.
The lefty-hitting first baseman put together a legendary Hall-of-Fame career, playing 19 years and enjoying his best years with the Padres and Braves as he slugged 30 home runs 10 times.
He totaled 493 home runs and amassed 56.3 WAR, per Fangraphs, and was inducted into Cooperstown in 2023.
Murray, meanwhile, was a mediocre reliever in New York while Dodd never got an at-bat with the Yankees and only spent one year in the big leagues.
From Prospect to Sworn Postseason Foe
The 1998 Yankees are often thought of as an untouchable, immortal team.
But they did make one grave mistake: trading Mike Lowell to the Marlins after the season ended.
In Feb. 1999, the Yankees traded Lowell, a fast-rising third base prospect, for pitchers Ed Yarnall, Todd Noel and Mark Johnson, feeling comfortable with their future at the position because of Scott Brosius’ stalwart 1998 season.
But Brosius never quite matched his 1998 performance again and Lowell became a star, piecing together a 13-year big-league career in which he smacked 223 home runs with an .805 OPS and made four All-Star teams.
What really turned the knife in the Yankees’ chest, though, was Lowell’s postseason play.
The third baseman helped the Marlins defeat the Yankees in the 2003 World Series, then joined the Red Sox and aided the Yankees’ most bitter rival in their 2007 championship, which ended the 86-year Curse of the Bambino.
Yarnall, Noel and Johnson completely busted, as only Yarnall made a big league appearance for the Yanks and that showing was bad — a 5.40 ERA in 20 innings.
Brian Cashman later said that it was the one deal over his 25-year tenure that stands out when he thinks about getting a re-do.
“What the hell did you trade Jay Buhner for?”
Perhaps no trade looms larger in Yankees’ infamy than this one, thanks to one Frank Costanza.
On July 21, 1988, the Bombers traded 23-year-old outfielder Jay Buhner for 33-year-old first baseman/designated hitter Ken Phelps.
Over the course of the rest of the season, the trade didn’t look so bad: Buhner had a .778 OPS for the Mariners and Phelps compiled a .890 OPS in New York.
The outlook would get much, much worse, though.
Buhner went on to star for the Mariners for 14 years, hitting 307 homers with an .857 OPS as he racked up All-Star nods and MVP consideration.
The trade prompted an all-time “Seinfeld” clip in which Costanza grills the show’s George Steinbrenner about trading Buhner away.
“What the hell did you trade Jay Buhner for?!” an agitated Costanza asks the Yankee owner. “He had 30 home runs and over 100 RBIs last year. He’s got a rocket for an arm… You don’t know what the hell you’re doing!”
The fictional Steinbrenner retorts that his baseball people really liked Phelps.
So much for Phelps’ longevity, though, because he only played one more half-season in pinstripes after 1988 and was out of the league by 1991.
The Joey Gallo Debacle
An outfielder with a sweet-swinging, lefty power stroke and a cannon for an arm?
If that sounds perfect for the 2020s Yankees, think again.
When the Yankees acquired longtime target Joey Gallo in a 2021 deal, bolstering an offense in great need of another bat, it seemed like a triumph for the Bronx Bombers.
It was most certainly not.
Gallo, a two-time All-Star and Gold Glover with the Rangers known for towering home runs and a penchant for striking out and walking — a king of the three true outcomes — tumbled to historic lows with the Yankees.
The lefty outfielder hit .159/.291/.368 with 23 home runs over two years with the Yanks, striking out 38% of the time as fans in the Bronx relentlessly booed his dismal performance.
Meanwhile, the return for the Rangers has helped jumpstart the team’s rapid rise to contention: Texas acquired Ezequiel Duran, Josh Smith, Glenn Otto and Trevor Hauver.
Duran appears to be the lodestar of the deal, as the 24-year-old infielder has been brilliant for the first-place Rangers this year, hitting for a .820 OPS and 13 home runs while playing solid defense across the diamond.
The Yankees did recoup some value on Gallo by passing him off to the Dodgers in 2022, acquiring minor-league starting pitcher Clayton Beeter for him, who had a 2.08 ERA in 60 Double-A innings this year.
The Ace That Got Away: Doug Drabek
Just when you thought the trades couldn’t get any worse for the 1980s Yankees, they did.
In 1986, the Bombers traded 23-year-old Doug Drabek along with Logan Easley and Brian Fisher to the Pittsburgh Pirates for Pat Clements, Cecilio Guante, and Rick Rhoden — one of the many blunders that would set their 80s squads back.
After Drabek tossed a respectable rookie season in The Bronx, earning a league-average 4.10 ERA in 131.2 innings, he exploded onto the scene in Pittsburgh, winning a Cy Young over six years as one of the team’s aces.
Drabek finished a stellar career after 13 seasons with stints in Houston, Chicago and Baltimore, amassing 29.2 WAR, per Baseball Reference.
Easley and Fisher also found homes in the Pirates’ pitching staff, serving as a reliever and a starter, respectively, for a few seasons.
Meanwhile, the Yankees’ return aside from Rhoden didn’t serve them very well — neither Clements nor Guante was successful in the Bombers’ rotation, while Rhoden turned in two serviceable years at the twilight of his career.
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