New York Yankees Exec Brian Cashman Made a Mistake Signing Randy Winn

Last offseason, the Yankees were in the market for an outfielder that could hit lefties. The tricky thing was that Johnny Damon was a free agent.

The Yankees didn’t want Damon, though. They didn’t want to deal with the hassle of dealing with his agent Scott Boras and certainly didn’t want to give in to his multi-year contract demands.

The Yankees had long-term plans that Damon’s multi-year deal would have interfered with. They also had a young outfielder named Brett Gardner , who has had such flashy defense that they felt compelled to give him a shot.

The Yankees tried to make it clear that they weren’t interested in Damon, despite the fact that nobody believed them, myself included.

At the same time, they were looking for a bat that they could platoon against lefties. In their pursuit of this bat, they established very publicly that they were only looking to spend $2 million tops.

Their net was not cast wide enough for Damon, but it turned out that it was wide enough to catch Randy Winn . Winn is somebody that Brian Cashman has liked for years. He’s been trying to trade for him since his days with Seattle.

Winn had just come off a year where he was getting paid $8.25 million while Cashman had been dealing with a stubborn player all offseason. My guess is that he couldn’t believe that Winn, with all of his experience, was so willing to take what was obviously a low-ball offer.

The Yankees said all offseason that they were searching for an outfielder who could hit lefties and signed Winn instead.

Winn had been good throughout his career against lefties, but in recent years he has become over-matched by them. He was 0-for-11 against southpaws as a Yankee. Winn’s contract was loaded with incentives for plate appearances against lefties ,and in the end, he faced them 11 times.

Luckily for the Yankees, they were able to nab Marcus Thames on a Minor League contract, and he’s worked out pretty well. But it does say a lot that the Yankees cut Winn before it’s even June. It signals that they realize they made a mistake.

Keeping Kevin Russo around, a guy who until this season had never played a single game in the outfield, in Winn’s place is another sign that they realize they’ve made a mistake.

Another related note, with Russo on the roster and the Yankees in the market for an outfield bat (ESPN’s Jayson Stark reported this yesterday ) Ramiro Pena should be very worried about his spot on the roster. If Russo keeps playing well and the Yankees do trade for a bat then it could be the end for Pena.

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