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The best trades Brian Cashman ever made

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There have definitely been some winners in his time

Alex Rodriguez News Conference Photo by Jim McIsaac/Getty Images

Every general manager in baseball has made good trades and bad over their career. I’d like to think that Brian Cashman has mostly made good trades, but there are definitely some bad ones mixed in there. Here are what I believe to be the best of the bunch. We can go over the worst at another time.

For those that will ask, I considered the players on either side of the trade, how long the players were under team control for, and how everyone performed after the deal was made.

The Nick Swisher Trade

I don’t want to play favorites with the transactions I list here, but there’s no way the Nick Swisher trade isn’t the clear winner out of all the rest. In the offseason before the 2009 season, the Yankees didn’t have a starting first baseman. Before they even entered into the bidding for Mark Teixeira, Brian Cashman pulled a deal to acquire Nick Swisher from the White Sox, and claimed he would be the team’s starting first baseman. Obviously, no one bought it, they signed Teixeira, and the rest is history.

However, it’s important to remember just how important Nick Swisher was to the Yankees from 2009-2012. In the early part of his first season in pinstripes, Swisher was a bench player behind Xavier Nady, until the latter was lost for the year to an elbow injury. Swisher went on to play at least 148 games in every one of his seasons as the team’s starting right fielder (and occasional first baseman). At the end of his contract, he had hit .268/.367/.483 with 105 home runs and an appearance in the 2010 All-Star Game to show for it. He provided the team 14.6 WAR to blow away the collection of scrubs used to acquire him in the first place. Good job, Chicago.

For some reason, the White Sox were happy with a return of Wilson Betemit, Jeff Marquez, and Jhonny Nunez. Betemit had been acquired by the Yankees the year prior, and was no better than a utility player. He ended up playing 20 games for the White Sox before he was released. Marquez and Nunez spent several years in their system before Marquez found his way back to the Yankees for a handful of innings in 2011, and Nunez went off to play Caribbean baseball. Somehow the Yankees also received a warm body back in Kanekoa Texeira, who managed to be of no consequence whatsoever.

The Bobby Abreu Trade

By midseason in 2006, the Yankees were trailing the Red Sox by one game, and were tied with the White Sox for the Wild Card. That would obviously just not do, so Brian Cashman targeted a bat to help them bust through the competition. The target would be 32-year-old Bobby Abreu, who was hitting .277/.427/.434 with eight home runs, 20 stolen bases, and a walk rate of 20%.

The Yankees got him for a song and dance, sending C.J. Henry, pitchers Matt Smith and Carlos Monasterios, and catcher Jesus Sanchez to the Phillies in exchange for Abreu and Cory Lidle. The team’s new right fielder hit .330/.419/.507 with seven home runs, 10 stolen bases, and continued to walk. In fact, he remained with the team for the 2007 and 2008 seasons, hitting .295/.378/.465 with 43 home runs and 57 stolen bases by the time his Yankees career was all said and done. That kind of production only cost them $31 million.

While Abreu found success in New York, Henry–a 17th overall pick from the year before–was out of baseball by 2008 as he tried to pursue a career in basketball. Smith threw 12 innings for Philadelphia before he too was done with baseball by 2008. Monasterios managed to throw 88 innings for the Dodgers in 2010 before joining the Mexican League. Sanchez appears to be the only player still in baseball, but has never played in the majors. Talk about a steal.

Lidle was tragically killed in a plane crash just months after the deal was made.

The Didi Gregorius Trade

Yes, it’s still early, but I think it’s clear that when everything is said and done, this will be one of the best deals Cashman ever made. In the second three-way trade of his career, Didi Gregorius was acquired by the Yankees before the 2015 season in order to begin a new era at shortstop now that Derek Jeter was gone. Under team control for the next three seasons, this could be a defining trade of the post-Jeter era.

Known for his glove and anemic bat, Gregorius maintained a .243/.313/.366 batting line with 13 total home runs over just 724 plate appearances for two different teams across three seasons. He never really got much of a chance to play consistently, so going in, he seemed like a little bit of a project. Didi was young at just 25 years old, and he was cheap, making the league minimum. In the deal that sent him to New York, the Yankees traded Shane Greene to the Detroit Tigers. He had just come off a promising season with a 3.78 in 78 innings, making people nervous about the acquisition.

The deal has so far worked out quite well, as Gregorius seemingly unlocked his offensive potential. In two seasons, the Yankees shortstop has hit .270/.311/.409 in regular playing time, jumping his power from nine home runs in 2015, to a full 20 in 2016. Meanwhile, Greene has struggled mightily in Detroit, pitching to a 6.88 ERA in 83 innings in his first year with the team before it was discovered he suffered an aneurism in his hand. He returned the next year, but could only manage a 5.82 ERA over 60 innings. Given the return for what they had to give up, I’d say this is one of the better deals Cashman has ever made.

The Curtis Granderson Trade

Since the deal originally happened, the merits behind this trade have been debated back and forth for years. No one involved in the deal is with the team they were dealt to any longer, so it’s probably a good time to look back on this trade and wonder.

It’s important to remember that the Yankees got 15 WAR in four years from Granderson, and it would have probably been more if not for all the bad luck and broken bones in 2013. Throughout his career with the Yankees, Granderson was criticized for his low batting average, but ultimately provided a very valuable .245/.335/.495, which translates to 120 OPS+. He hit 115 home runs in that time, accumulated 307 RBI, and stole 55 bases. He also made the All-Star team twice, won a Silver Slugger Award, and ranked fourth in American League MVP votes in 2011. How could the Yankees not have won this trade?

To acquire Granderson in the first place, Cashman had to give up Phil Coke, Austin Jackson, and Ian Kennedy. At the time it seemed like an awful lot, but now it would have been looked at as a joke. Coke was thought to be a solid left-handed option in the bullpen, however the Tigers had the misguided idea of making him a starting pitcher. After a few years spent with an ERA north of 4.00, he moved on before making it back to New York just this season.

Austin Jackson was easily the hardest piece to give up in this deal. He was considered to have the upside of Granderson himself, but the cheaper cost and additional years under control made the trade debatable. He played well with the Tigers, hitting .277/.342/.413 with 46 home runs, collecting double digits in triples almost every year, and nearly winning the Rookie of the Year Award. Following Granderson’s 6.8 WAR season, Jackson answered back with a 5.8 WAR in 2012, but that’s ultimately where he peaked. Over the last three seasons, Jackson has played for five different teams and been about a league-average hitter or worse. He missed most of the 2016 season to knee surgery, and it doesn’t look promising for him.

The last piece the Yankees gave up in the deal was Ian Kennedy, who turned out to have the most successful career among Joba Chamberlain, Phil Hughes, and him. After a few good years out in Arizona where it looked like he could feast on NL hitters in a bigger ballpark, he became a replacement level starting pitcher with the Padres. Thanks to some weird market valuation, the Royals decided to sign him to a lucrative four-year deal, and he didn’t turn out too bad. The Yankees could definitely use his ability to reach around 200 innings in a season, but his flyball tendencies would have made him a poor fit at Yankee Stadium. They were right to give him up when they did.

The Brandon McCarthy Trade

This was a hilarious trade the Yankees made for multiple reasons. They transformed Vidal Nuno, someone they signed out of Indy ball the year before, into one of the best pitchers in the second half of the 2014 season. Nuno seemed to be a solid young lefty who dominated the minors, but couldn’t quite cut it in the big leagues. He had some positives, but nothing close to what someone like Brandon McCarthy could bring to a team that desperately needed some quality pitching.

What made this trade weirder was finding out just how bad the Diamondbacks regime was at handling their pitchers. That year, the normally solid McCarthy struggled in his time with Arizona. He had a 5.01 ERA at the time of the deal, and it left people scratching their heads as to why the Yankees would want such a pitcher. As it turned out, Arizona had muddled with McCarthy’s arsenal of pitches, trying to turn him into an extreme ground ball pitcher. The results were obviously disastrous, but the Yankees were able to reverse the damages done, and their new pitcher pitched to a 2.89 ERA with a 3.22 FIP in 90.1 innings.

Nuno, meanwhile, has bounced around a bit since the trade. He was previously used as a swingman, but spend most of the season in the Mariners bullpen this year. Despite decent numbers, he hasn’t offered a whole lot of value. McCarthy turned his incredible turnaround into a longterm contract with the Dodgers, only to blow out his elbow in his first season with them after pitching 200 innings for the first time in 2014. McCarthy has always been injury prone, so it’s a good thing the Yankees got him healthy while they could.

Honorable Mentions:

  • Kerry Wood for Matt Cusick and Andrew Shive
  • Michael Pineda and Vicente Campos for Jesus Montero and Hector Noesi
  • Ichiro Suzuki for Danny Farquhar and D.J. Mitchell
  • Chase Headley for Yangervis Solarte and Rafael De Paula
  • Starlin Castro for Adam Warren and Brendan Ryan