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The five worst one-year deals of Brian Cashman’s career

Some of these deals were ugly

Cleveland Indians v New York Yankees

One of the only free agent signings the Yankees made this offseason was a one-year deal. Brian Cashman signed outfielder Matt Holliday to a $13 million contract as he enters his age-37. We don’t know how that deal will end up, but Cashman has certainly made some bad signings in his career. Instead of looking at every multi-year contract—because that’s an article for another time—I focused on one-year contracts and came up with his five worst.

Kevin Youkilis (2013)

The 2013 season was a weird year for a lot of different reasons, but it was primarily terrible because everyone got hurt. Derek Jeter, Mark Teixeira, Curtis Granderson, and Travis Hafner were limited by injury, and Alex Rodriguez missed the first half of the season. It was also the year that new third baseman Kevin Youkilis got hurt too.

Before the season, the Yankees sought a replacement at third base while A-Rod underwent surgery on his hip. Youkilis had struggled during the 2012 season while Red Sox manager Bobby Valentine publicly ran him out of town on a rail. He looked old, his numbers were down, and his back wasn’t holding up. They traded him to the White Sox in June and things got better. He hit .236/.346/.425 with 15 home runs in 80 games with Chicago, reestablishing his eye at the plate and rediscovering his power stroke.

The White Sox explored bringing him back, but Brian Cashman—using their offer as a show of confidence in his abilities—felt comfortable enough to offer Youkilis a $12 million one-year contract. The expectation was that he would have regular playing time at third while A-Rod was out and could also provide depth at first base behind Mark Teixeira.

Things did not work out that way. wYoukilis made it as far as April before injuring his back. He missed most of May, returned for half of June, and was out for the rest of the season after aggravating the injury and undergoing surgery to fix a herniated disc. Not only did the Yankees get only 28 games out of their offseason signing, he wasn’t all that productive when he was on the field. Youkilis hit .219/.305/.343 and was worth -0.5 WAR over just 118 plate appearances. It felt like everyone but the Yankees saw this coming.

David Cone (2000)

Right-handed pitcher David Cone was a big part of the team’s success in the 1990s. The Yankees GM Bob Watson acquired him in 1995 before signing him to a three-year deal. Brian Cashman took over in 1998 and brought him back on a one-year deal for the 1999 season. To this point, Cone had been very successful in the Bronx. He maintained a sub-3.00 ERA in his first two seasons and then averaged around a 3.50 ERA the following two seasons. It seemed like a good idea to keep it going.

Cashman brought Cone back on another one-year deal for the 2000 season, and everything went wrong. That year, he pitched to an ugly 6.91 ERA with a 5.44 FIP over 155 innings. He proved to be extremely hittable and was responsible for 14 of the team’s losses all by himself.

As good as Cone had been, it turned out that the Yankees brought him back one season too many. It’s no surprise that they let him go elsewhere that offseason, and his career was nearly over by then.

Freddy Garcia (2012)

The Yankees had struck gold by signing elder statesmen Bartolo Colon and Freddy Garcia for the 2011 season. Both did fairly well, with Garcia pitching to a 3.62 ERA with a 4.12 FIP in 146.2 innings. It was a far better season than anyone ever thought Garcia was capable of at the time. Despite his success, most fans thought one season was enough and the Yankees should look elsewhere for a rotation upgrade.

For some reason, Brian Cashman felt that it was a good idea to not only bring him back, but also sign him to a $4 million deal in December of the offseason. It was as if the Yankees were adding a piece off the scrap heap before they even had time to look for someone better. Things obviously didn’t go too well for him because he finished with a 5.20 ERA, gave up even more home runs than he did the previous year, and eventually lost his spot in the rotation.

What made this signing so bad was the fact that the Yankees chose the wrong old guy to re-sign as Colon went on to have a solid career resurgence. They also chose Garcia over someone like Mark Buehrle, who would have been perfect at the time, and international players Yu Darvish and Hisashi Iwakuma.

Nick Johnson (2010)

This probably ends up being Brian Cashman’s dumbest decision as general manager of the Yankees. Gifted with a great eye but an injury-prone body, Cashman moved him in the (first) Javier Vazquez trade. Johnson went on to find some success in between his stints on the disabled list.

In 2010, the Yankees needed a new DH after they decided to move on from Hideki Matsui. Brian Cashman thought it was a good idea to re-sign Johnson to a $5.5 million deal with a team option. The thought must have been that if he could just stay out of the field for a full season, his body would hold up and the production would be there. While this was sound in theory, Cashman had to know that Johnson would never stay healthy for very long.

As it turned out, he could still walk but wasn’t able to hit much at all. He hurt his wrist just 24 games into the season and was never seen again. He underwent surgery on his wrist in August and the Yankees decline their option on him. The Yankees clearly thought they had their long-term option at DH, but it proved to be a big mistake.

Stephen Drew (2015)

The Yankees struck a deal with the Red Sox during the 2014 season, sending over Kelly Johnson to acquire Stephen Drew. It was a small way to improve the team and give them a chance to evaluate what he could do for them in the future. Somehow a 150/.219/.271 performance proved to them that Drew was worth a $5 million deal in 2015.

That year, the team’s new second baseman hit .201/.271/.381 for the Yankees while still somehow managing to hit 17 home runs on the year. He proved to be a complete non-factor for the team and this deal became a ugly representation of the post-Robinson Cano Yankees.

Honorable mentions: Roger Clemens (2007), Andruw Jones (2012), Travis Hafner (2013), Brian Roberts (2014)