Did the Red Sox Plant Jacoby Ellsbury in the Yankees Organization as a Double Agent?

The Jacoby Ellsbury era in New York is over. And what a ride it was. Is this potentially the worst contract in New York Yankees history?

After the Red Sox came together after the tragic Boston Marathon attack, grew beards in solidarity together and won the World Series, Ellsbury was out of here. And honestly, I’m not going to be one of those guys that rips him for taking the LOAD of money that the Yankees threw at him like we did with Johnny Damon. Damon was a little different because he specifically said he wouldn’t be a New York Yankee. And, well, he went back on that pretty quickly.

Ellsbury just packed his bags and left after he got a ring and went to one of the most storied franchises in baseball. I’m not going to hate on him for that. But my God, would I be lying if I said seeing him create mayhem for the Yankees wasn’t pure poetry.

The contract was massive. It was a 7-year, $153 million deal that they’ll continue to pay through the 2020 season and at the time it made sense for the Red Sox to just let him go. That’s a ton of money for a guy who, let’s be honest, couldn’t stay healthy and that’s what ended up being the issue during his time in New York.

He missed most of the 2010 and 2012 seasons while he was in Boston but once he got to New York, he semi-cruised through the first four years of his new contract and was available most of the time. But man, did his stats DROP like a nuclear bomb in North Korea.

The best batting average he produced while in New York was .271. When he was a member of the Red Sox he was the runner up for the AL MVP in 2011 and overall was a damn good player when he was on the field. When he was on, he was electric. Nothing gets the juices flowing like someone stealing home and he was nuts at it.

But again, he was fragile as all hell during that span.

Once he got to New York he was good for the most part health-wise. But he hasn’t played a SINGLE game for the Yankees since the 2017 season. The injury that’s probably the most notable was the torn labrum in his hip. Look, I’m not going to pretend that I’m a doctor here or that I know what I’m talking about, but that sounds painful.

Over those last two years? He’s made a little north of $21 million in BOTH seasons. MY GOD CAN SOMEBODY ARREST THIS MAN FOR ROBBING BRIAN CASHMAN BLIND!?

It’s unbelievable that they thought this would work. Now, I get it. The guy was a solid talent in Boston. I hated that he’d end up on the disabled list–because that’s what it was called at the time, narcs–anytime he’s trip over a stray sunflower seed in center. That entire aspect of his tenure in Boston made me nuts. But he came up through the Red Sox farm system and won two World Series with the team so I’ve got a tough time trying to bury him.

This was absolutely all John Henry. He knew what he was doing. He had a meeting with Jacoby before free agency, was straight up with him, told him that the Red Sox weren’t going to pay him but probably slid him $20 and some high-end toothpaste to become a useless piece of wood in the Yankees’ organization. I don’t like to throw around the term “perfect crime” too often but it might be applicable here.

RIP to the Jacoby Ellsbury era in the MLB that died after the 2017 season. Well, unless he makes a comeback. In Boston, we’ve seen Carl Crawford and Pablo Sandoval’s contracts both want to make fans claw their eyes out. But his… his contract might have been the worst deal signed by an MLB team in the 21st century.

The only thing that would make this better would be if the Red Sox ended up signing Ellsbury back–only if they trade away Mookie Betts–and he ends up playing in 140 games while hitting over .300. That would be the bow on this insane gift.

-Nick Quaglia (@NickQuag)

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