5 worst Brian Cashman Yankees signings ranked after Marcus Stroman release

The New York Yankees officially ended the Marcus Stroman era on Friday, releasing the veteran starting pitcher after two frustrating seasons in pinstripes.

Stroman went 13-11 with a 4.69 ERA in nearly 200 innings as a Yankee, and his departure caught some off guard, given the club’s various rotation issues. His release came less than 24 hours after allowing four runs in five innings against the Rays, though he at least earned the win.

Stroman is the latest failed Yankees signing under Brian Cashman, but is he the worst? Between his stats and his attitude, he certainly has an argument to rank among the top contenders.

In creating this list, we had two specific requirements: the first being that players must have been external additions, and those on one-year contracts were ineligible. That means that Alex Rodríguez’s 10-year, $275 million deal doesn’t qualify because Rodríguez had opted out of his previous deal.

Here are who we believe are the Yankees’ five worst free agent signings in the Brian Cashman era.

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5) Marcus Stroman, SP (Two years, $37 million)

Any remaining Stroman defenders might question why he ranks fifth ahead of the likes of Jaret Wright, AJ Burnett, or even Brian McCann. The Stroman contract lands on this list mainly because of how he carried himself, especially in spring training earlier this year. Stroman briefly held out and publicly declared that he wouldn’t pitch out of the bullpen. Although then-Boston Red Sox third baseman Rafael Devers took a similar stance about playing first base or DHing, at least Devers was a perennial MVP candidate.

Stroman, on the other hand, was so mediocre in 2024 that the Yankees removed him from the rotation in September. If not for injuries to Gerrit Cole and Luis Gil, Stroman likely would have started the season as a long reliever — assuming, of course, that the Yankees wouldn’t have just cut or traded him then.

In hindsight, Stroman was never a good fit for the Yankees, and we have a feeling he’ll never be invited to Old Timers’ Day.

4) Pedro Feliciano, RP (Two years, $8 million)

The worst part about the Pedro Feliciano contract is that he never pitched for the Yankees. Feliciano missed the entire 2011 and 2012 seasons with severe left shoulder injuries, specifically a torn anterior capsule and rotator cuff.

The Yankees, naturally, blamed Feliciano’s issues on the rival Mets overusing him, and they’re not wrong. Mets managers Willie Randolph and Jerry Manuel pitched Feliciano a staggering 266 times from 2008-10, with him appearing in 92 games during that final season. We’re not sure that “MLB: The Show” would even let you use a reliever that often without consequences. 

Younger baseball fans might be unfamiliar with a LOOGY (or a Lefty One-Out GuY) a role that the three-batter minimum has effectively erased. Feliciano only threw 175 1/3 innings across those 266 games because he’d typically face one or two batters. Looking back, it’s incredible that Feliciano didn’t get hurt earlier, and it’s too bad that the injuries ruined his career. 

3) Jacoby Ellsbury, OF (Seven years, $153 million)

Much of the Yankees fanbase would likely contest Ellsbury’s place here and suggest that he’s the worst signing in team history. And, in fairness, they’re not wrong in thinking so, not after Ellsbury hit .264 with 39 homers, 102 stolen bases, and a .716 OPS from 2014-17. 

Of course, the problems arose during the back half of Ellsbury’s contract. The former Red Sox star missed all of 2018 and 2019 following various injuries, including a hip problem and a severe foot ailment. The Yankees then didn’t want to pay Ellsbury after alleging he sought unauthorized medical care, the situation went to court, and he eventually received the money owed.  

At least Ellsbury played, though. Considering how things ended, it's easy to forget that Ellsbury stole 39 bases in 2014 and averaged 2.4 bWAR over his four Yankees seasons. By no means is that what the Yankees paid for, but it’s certainly a better output than the next two players.

2) Carl Pavano, SP (Four years, $39.95 million)

It’s bad enough that Pavano went 9-8 with a 5.00 ERA across 145 2/3 innings and 26 starts in four seasons. Various injuries, including Tommy John surgery and not telling the Yankees about breaking two ribs in a car accident, kept Pavano sidelined for much of his tenure in the Bronx.

Things were so bad that teammate Mike Mussina publicly called Pavano out in 2007, questioning why Pavano couldn’t play through injuries and even admitting that the veteran starter needed to regain his teammates’ respect.

“He needs to show a lot of people that he wants to go out there and pitch for us,” Mussina told reporters. “If he shows us that, I think everything is going to be fine.”

Mussina even noted that every time Pavano was supposed to come off the injured list or make a rehab start, another injury popped up.

“From a player’s and a teammate’s standpoint, it didn’t look good,” Mussina argued. “Was everything just [a] coincidence over and over again? I don’t know.”

Pavano had a legitimate case to top this list, and we came so close to ranking him No. 1. However, there’s one more player that we’d like you to meet.

1) Kei Igawa, SP (Five years, $20 million, plus a $26 million posting fee)

The 2006-07 offseason featured numerous Japanese pitchers making their way stateside, with Daisuke Matsuzaka and Hideki Okajima joining the Red Sox. Yankees fans got a late Christmas gift on Dec. 27, 2006, when Hanshin Tigers star Kei Igawa inked a five-year deal to bolster the starting rotation.

Igawa didn’t last long, moving to the Yankees’ bullpen after only a month in the majors. The Yankees demoted Igawa to Single-A in early May, and he never regained his rotation spot. Things got worse in 2008, when Igawa made two appearances and allowed six runs in four innings.

What gives Igawa the top spot, though, is how his time with the Yankees ended. Igawa spent all of 2009-11 in the minors, mostly at Triple-A, despite the Yankees telling him he’d never pitch for the big-league club again.

“It was a disaster,” Cashman said. “We failed.”

That, right there, is how you earn the top spot on a list like this.