By Ryan Nelke

Header Credit: Reflections on Baseball

Thumbnail Credit: The New York Times

Once again, Yankees fans go into the offseason without a championship for the 13th straight year.  This does not fit the theme of a franchise defined by constant success, as they hold the record for the most World Series titles–27– in MLB history.  There is plenty of blame to go around, but when the dust settles, it all comes down to who assembled the team.

“I don’t think the Yankees are headed in the right direction,” Mike Francesa, a former sports talk show host for WFAN said.  “There comes a time that you need a new voice and you need a new direction.  Moving on would be the smartest thing they could do now, because this team needs wholesale changes.”

In the past five years, Yankees general manager Brian Cashman has made some head-scratching moves that have disappointed many fans and impacted their ability to get that elusive next championship.  Now, as Yankee faithful are currently left with the sour taste in their mouths of the ALCS sweep, it seems like an appropriate time to look back on Cashman’s top five worst moves over the past five years.

#5: 2022; Yankees Trade for Josh Donaldson and Isiah Kiner-Falefa

Going into the 2021 offseason, the Yankees had a glaring problem at catcher.  His name was Gary Sanchez.  Sanchez had put up abysmal numbers at the plate during the season, and to go along with that, he was a liability behind the plate.  The Yanks also were looking to improve the left side of their infield, so Cashman swung a deal with the Minnesota Twins to acquire third baseman Josh Donaldson, utility infielder Isiah Kiner-Falefa, and catcher Ben Rortvedt for third baseman Gio Urshela and catcher Gary Sanchez.  However, the 2022 season would prove that this move did not do anything to improve the left side of the infield.

“That is going to go down as one of the worst trades that [Brian] Cahsman’s ever made because you accepted $50 million in Josh Donaldson’s contract, Michael Kay, the Yankees TV announcer said.  “That deal is going to haunt them for a long time, a long time.”

While Donaldson provided solid defense at the hot corner, his bat just could not come to par with acceptable numbers.  He hit .222 with 15 home runs and 62 RBIs, along with his on-base percentage and slugging percentage being the lowest of his career since he became an everyday player back in 2013.  In contrast, former third baseman Urshela (who was $19 million cheaper than Donaldson) posted an exceptional .285 average with 13 home runs and 64 RBIs.  In addition, “IKF,” as Yankees fans called him, was not much better.  His defense was below average for a shortstop and his numbers at bat were nothing to write home about, as he hit .261 with 4 home runs and 48 RBIs.  For a shortstop who does not have great defense and does not hit for a high average, you would hope they hit for power and knock runs in.  IKF proved his inability to do so.

#4: 2022; Yankees Trade for Frankie Montas

In an attempt to bolster the pitching staff as the Yankees inched closer to the postseason, Cashman made a trade deadline acquisition, as New York brought in starting pitcher Frankie Montas and reliever Lou Trivino for four prospects, which included starting pitchers JP Sears, Ken Waldichuk, and Luis Medina, as well as second baseman Cooper Bowman.  

“The righty was supposed to come in and be the No. 2 arm in the rotation, but instead he committed three cardinal sins–he was bad, with a 6.35 ERA as a Yankee, he worked extremely slow, and he got hurt,” Joshu Diemert, a writer for Pinstripe Alley said.

In his eight outings, Montas went 1-3 with a 6.35 ERA and failed to record even one quality start (when a pitcher throws six innings and allows three runs or fewer).  Most of his starts did not even come anywhere near being considered anything but just downright awful.  What made this worse was the Yanks gave up two budding prospects to get him.  The Bronx Bombers had recently called up Sears and he was putting up solid numbers.  Additionally, this trade meant that New York had to part with their #5 prospect Waldichuk and #10 prospect Medina.  This trade did not just symbolically represent a minor vehicle accident…it represented a car flying off a cliff.

#3: 2017; Yankees Trade for Sonny Gray

At the 2017 trade deadline, Cashman acquired starting pitcher Sonny Gray for three prospects, being starting pitcher James Kaprelian, shortstop Jorge Mateo, and outfielder Dustin Fowler.  From the beginning, Sonny Gray showed he could not handle the New York atmosphere.  

“At the time, it was viewed as a moderate package, but the necessary price you’d pay for a potential ace,” Adam Weinrib, a writer for Fansided said.  “Now? It looks like two tweeners and a sad story.”

In his season and a half in pinstripes, Gray posted a 15-16 record with a 4.51 ERA, and not before long, he would be sent off to Cincinnati.  During his short stay in New York, it was filled with upset fans and a constant theme of disappointment.  While the prospects the Yankees sent away so far have not turned out to be stars, it takes a spot on this list as it remains shocking that New York had to give up anything for an extremely ineffective pitcher.

#2: 2019; Yankees Re-Sign Aaron Hicks

If it was not for Joey Gallo, Aaron Hicks would have earned the #1 spot on this list.  During the 2019 offseason, Cashman chose to extend outfielder Aaron Hicks, by awarding him a 7 year, $70 million contract, which would keep him under contract through the 2025 season.  However, between poor play and a mounting injury history, nothing at all has gone right for Hicks.

“From back spasms to Tommy John surgery…his medical file reads longer than Peter Griffin’s bar tab,” Josh Benjamin, a writer for Elite Sports NY said.

In the four seasons following his extension, Hicks has failed to hit better than .235, has failed to hit more than 12 home runs, and has failed to rack up more than 40 RBIs.  In addition, Hicks’ defense had become so unbearable that he was removed from a game due to an unforgivable blunder.  For a guy paid $10 million a year for a mind-boggling seven years, these numbers are just unacceptable.  His endless injury history is the icing on the cake, cementing his spot at #2 on Cashman’s worst blunders.

#1: 2021; Yankees Trade for Joey Gallo

Even with how bad the Hicks extension was, the Gallo deal makes that look like a small slip-up.  At the 2021 trade deadline, Cashman acquired outfielder Joey Gallo and reliever Joely Rodriguez from the Texas Rangers for four minor league prospects, including starting pitcher Glenn Otto, second baseman Ezequiel Duran, shortstop Josh Smith, and utility man Trevor Hauver.

“They did not go out of their way to boo a guy who was actually doing a decent job…this guy earned the boos,” Michael Kay, the voice of the Yankees said.  “He was a failure here in New York.”

Even labeling Gallo a failure may have been an understatement.  In 140 games with the Bombers, he produced a putrid .159 batting average and by the time of his second season in pinstripes, he struggled to hit the ball out of one of the most hitter-friendly parks in the MLB.  Gallo’s time as a Yankee will always be remembered as a parody for how bad a professional baseball player could be and is arguably the worst Yankee to ever don the pinstripes, making him an easy choice for the #1 slot on this list.

What Does the Future Hold?

From the Donaldson and IKF deal all the way down to Gallo, it proves to be an indictment on the recent tenure of Cashman, the general manager of, historically, the most successful franchise in MLB history.  

“At some point, the Yankees need to take a long look in the mirror and understand that the philosophy is broken and a new voice is needed,” Stephen Leonardi, a writer for Bronx Pinstripes said.