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The five worst trades Brian Cashman ever made

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Bad mistakes, he’s made a few

MLB: New York Yankees at New York Mets Brad Penner-USA TODAY Sports

Brian Cashman has made many great trades, but he’s also made a few mistakes over the course of his career as Yankees general manager. None of them were incredibly costly to the future of the organization, but I bet there are some he’d like to have back if he could.

The Mike Lowell Trade

Without a doubt the most misguided trade in the Brian Cashman era of the franchise. I guess we’ll chalk this one up to him being young, inexperienced, and maybe drunk, but it still looks bad in retrospect. Mike Lowell made his major league debut in 1998 as a 24-year-old kid. Unfortunately for him, Scott Brosius was the Yankees’ third baseman, and would be there for the next four years, so Lowell had no place to play.

Now, I understand trading someone who is blocked, but the return was nearly non-existent. Ed Yarnell was a young arm who was traded away just a year later. Mark Johnson was taken away in the Rule 5 Draft, and Todd Noel was out of baseball by 2000. Considering Lowell had hit 26 home runs in Triple-A that year with an OPS just shy of .900, I have to wonder how they could not find a place for him on the team somewhere. If you look at his number career numbers, it’s hard to see how Brosius is the guy to drive a young prospect away, but when you hit .300/.371/.472 on the season, I guess there’s no way anyone is touching your job.

Lowell, of course, went on to have a great career, hitting .272/.339/.462 with 143 home runs as a Marlin. In that time, he was an All-Star three times, won the Silver Slugger and Gold Glove, received some MVP votes in 2003, and won the World Series. He ended up doing even better for the Red Sox, hitting .290/.346/.468 with 80 home runs to finish out the remainder of his career. In 2007, he was an All-Star, a World Series champion, and finished fifth in that year’s MVP voting.

While Lowell was off having himself a pretty nice career, Brosius was never as good as he was in 1998 (duh). He retired after the 2001 season and was replaced by Robin Ventura, who was an All-Star in 2002. He was shipped out during the following year and the era of Aaron Boone began, which led to Alex Rodriguez, which made everything ok again. Still, trading Lowell like that was a terrible deal to make.

The Tyler Clippard Trade

Back in 2007, the Yankee Clippard was a 22-year-old starting pitcher making his major league debut. He wasn’t very good, so despite the nickname, he was pretty expendable. After the season, he was shipped out to the Washington Nationals for a reliever by the name of Jonathan Albaladejo. It seemed like a forgettable trade filled with mostly forgettable people, except that no one had the idea to try Tyler Clippard out as a reliever yet. The Yankees had yet to perfect that art.

Life went on in 2008, Clippard struggled as a starting pitcher and New York’s new reliever threw a few quality innings. Then Washington had the bright idea to put him in the bullpen, and it actually worked. He became an underrated weapon with a 2.68 ERA and 3.46 FIP over seven years in DC. He was a two-time All-Star and had a stint as the team’s closer in 2012. Meanwhile, Albaledejo proved to be underwhelming for the Yankees, and they released him after the 2010 season. It’s not that the Yankees were lost without him, but the team’s bullpen sure could have used his help.

The Lance Berkman Trade

The Lance Berkman trade should have worked, but it managed to do absolutely nothing for the Yankees but release a quality reliever out into the world. In 2010, the Yankees were in the playoff hunt and they needed some extra firepower. Mark Melancon was a promising relief pitcher who had made his major league debut the year before, but never really got much of a chance the following year.

The Yankees must have felt they had enough relievers because they traded six years of Melancon, along with outfielder Jimmy Paredes, for half a season of Berkman so he could hit dingers and power the team through the playoffs. Unfortunately, it turned out that Berkman was incredibly uncomfortable playing in New York (he eventually admitted how scary it was) and never managed to hit much with a .255/.358/.349 batting line and one home run. Despite coming up with a key double in the ALDS, he didn’t hit in the playoffs, and in the end the whole trade looked like a waste of time.

Meanwhile, Melancon began to flourish with the Astros over the next two seasons. He was traded to the Red Sox and had a disastrous year in Boston before making his way to the Pirates where he became a big part of their bullpen. Over the four years he spent in Pittsburgh, Melancon held a 1.80 ERA and 2.27 FIP while collecting 130 saves as a three-time All-Star. He would have been another nice arm to have in the Yankees bullpen, but alas.

Both Javier Vazquez Trades

We’ll have two trades for this entry because Cashman had the bright idea to trade for Javier Vazquez on two separate occasions. The first time was in 2004, when they sent Nick Johnson, Randy Choate, and Juan Rivera to the Montreal Expos. This trade makes the list, not because of who they gave up, but because of the grief it gave the Yankees and their fans after just one season in the Bronx.

The Yankees signed him to a four-year extension when he came to New York at the beginning of the season because Cashman felt pretty confident. Vazquez was actually a very good pitcher, but something about pitching in the Bronx made him turn into sludge. That year he compiled a disappointing 4.91 ERA and 4.78 FIP in 198 innings. To make it worse, he allowed five runs in five innings against the Minnesota Twins in the ALDS, and then surrendered seven runs in 6.1 innings of relief against the Red Sox on their way to their improbable comeback. He blew Game 7, allowing two home runs to Johnny Damon, and by the offseason it was already time to move on. He was sent to Arizona in the trade that brought Randy Johnson to New York.

It seemed like the Yankees should have been done with him after that, but fate had other plans. Cashman was looking for pitching in 2010, and decided to give Vazquez another try, sending Melky Cabrera, Mike Dunn, and Arodys Vizcaino to the Braves for the 33-year-old and Boone Logan. Just a few months into the deal, we were calling this the Boone Logan trade because everyone else in it was terrible. Vazquez once again struggled in pinstripes and pitched to a 5.32 ERA with a 5.56 FIP in 157.1 innings, eventually losing his spot in the rotation toward the end of the season.

Thankfully, Vazquez retired after the 2011 season, preventing Brian Cashman from trying one more. Luckily, the Yankees never gave up anyone very valuable, as Johnson was too fragile to make much of his abilities, and Cabrera was one of the worst players in baseball until he got a little help from his pharmacist. It’s just too bad that Vazquez was kind of the worst.

The Jeff Weaver Trade

Another bad deal that ended in a lot of grief, the Jeff Weaver era for the Yankees was a bad one. Cashman thought he was getting a young pitcher on the verge of breaking out, but instead he became a disappointing mess. They sent Ted Lilly, John-Ford Griffin, and Jason Arnold out in a three-team trade in July 2002, hoping they had the arm that could put them over the top. He didn’t do too poorly during his first season in pinstripes, pitching to a 4.04 ERA, which was actually above average for the time period. He made two appearances in the 2002 ALDS, but allowed two runs in 2.2 innings as the Yankees were quickly booted from the playoffs.

The 2003 campaign was a complete disaster, however, as Weaver put up a 5.99 ERA and 4.26 FIP in 159.1 innings. By the end of August he was pushed into the bullpen. He didn’t pitch in the playoffs until Game 4 of the World Series. In a move much like Buck Showalter and Zach Britton this October, the game went into the 12th inning, and instead of ever going to Mariano Rivera in a tie game on the road, Joe Torre opted to give Weaver a chance for some reason. He allowed the walk-off home run to Alex Gonzalez that likely turned the series around in favor of the Marlins.

Weaver was sent packing in the offseason, but the damage had already been done. It’s debatable over how good of a career Ted Lilly might have had in the Bronx, but the lefty went on to have a successful career as a two-time All-Star while eating up innings and pitching at an above average rate. With his home run problem, maybe it never happens like that, but we’ll never know.

Honorable Mention:

Kevin Brown for Jeff Weaver, Brandon Weeden, and Yhency Brazoban.

Humberto Sanchez, Anthony Claggett, and Kevin Whelan for Gary Sheffield.

Austin Kearns for Zach McAllister.

Chris Stewart for George Kontos.

Vernon Wells for Exicardo Cayones and Kramer Sneed.