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The most disappointing trade deadline acquisitions of the Brian Cashman era

Andrew Heaney has not been what the Yankees expected, but he’s not the first disappointment to be reeled in at the deadline.

MLB: New York Yankees at Los Angeles Angels Gary A. Vasquez-USA TODAY Sports

When the Yankees acquired Andrew Heaney at the trade deadline this past July, they clearly hoped that the veteran lefty would at least be able to eat some innings at the back of the rotation, and they hoped that Matt Blake and the coaching staff might be able to unlock some untapped potential on the mound and turn him into a weapon down the stretch. Instead, Heaney turned out to be a massive disappointment — he was relegated to the bullpen after just five starts, and had not pitched in 10 days when he was opted to the Florida Complex League on Wednesday afternoon.

Heaney, unfortunately, is not the only trade deadline acquisition to fail to perform poorly upon donning the pinstripes. Let’s take a look at some of the biggest disappointments of the Brian Cashman era (1998—present). For the purposes of this article, only the performance of the year the trade occurred will be considered. As such, players such as Jeff Weaver, who was absolutely atrocious for the Yankees in 2003, is not on the list, as he was a serviceable starter — albeit not as good as hoped for — during the latter half of 2002.

Stephen Drew, 2014

When the Yankees acquired Stephen Drew from the Red Sox in a rare cross-rivalry trade, nobody really expected him to be a major threat at the plate. Sure, he had posted a 111 OPS+ the year prior, but he had posted a 62 OPS+ in 39 games in 2014, and had Statcast existed at the time, I’m sure it would have agreed that his performance was not a fluke, either. But with the Yankees trotting out the corpse of Brian Roberts on a daily basis, they hoped that Drew would rediscover the offensive spark he had found in 2013 and reinforce a lineup that was desperate for competence.

Somehow, Drew was even worse on the Yankees in 2014, slashing a less-than-pedestrian .150/.219/.271 — worse than pitchers Madison Bumgarner, Travis Wood, Zack Greinke, Shelby Miller, and Mike Leake!

Iván Rodríguez, 2008

With Jorge Posada out for the season after requiring surgery on his right shoulder, the Yankees sent Kyle Farnsworth to the Detroit Tigers for Iván Rodríguez, and although the deal weakened the Yankees bullpen, it gave them one of the best catchers in the league, at least on paper. It had been a few seasons since the Hall of Famer had been a truly potent bat in the middle of a lineup — after eight straight seasons with an OPS+ of 114 or above, he had posted just a 92 OPS+ from 2005 to 2007 — but he still got on base at a high clip (.338 OBP in 82 games with Detroit) and played above-average defense.

As a member of the Yankees, however, “Pudge” struggled at the plate, slashing just .219/.257/.323. He wound up splitting time with backup catcher José Molina (Chad Moeller and Francisco Cervelli also got a few starts down the stretch as well), playing only 33 of the final 54 games. The fact that he may have accidentally caused pitching phenom Joba Chamberlain to hurt his shoulder didn’t help, either.

Lance Berkman, 2010

The 2010 Yankees had big bats up and down the lineup, but thanks to Nick Johnson requiring surgery on his wrist, they lacked a regular designated hitter for much of the first half. With Marcus Thames, Mark Teixeira, Posada, and an assortment of others cycling through the DH slot, Cashman decided to reel in five-time All-Star Lance Berkman from the only team he had ever played for, the Houston Astros. Although he had not quite been hitting up to his career standards, he still had a 120 OPS+, and as a switch-hitting power hitter in Yankee Stadium, there was every reason to think that Berkman would have a bit of a renaissance in pinstripes.

That ultimately turned out not to be the case. Berkman hit only one home run in pinstripes, and although his ability to work walks allowed him to have a .358 OBP that propped up his OPS+ to an even 90, it was a far cry from what the Yankees were looking for.

Denny Neagle, 2000

Although they would go on to win their third straight World Series, the 2000 Yankees were by no means a juggernaut. In desperate need of competent starting pitching by somebody not named Roger Clemens, Andy Pettitte, or Orlando “El Duque” Hernández, they sent Drew Henson, Jackson Melián, and Ed Yarnall to the Cincinnati Reds for Denny Neagle, a two-time All-Star with playoff experience and a 3.52 ERA (a 135 ERA+) in 18 starts for the Reds.

What nobody knew at the time, however, was that all of Neagle’s quality baseball was in the rearview mirror. In 16 games (15 starts) in pinstripes, he went 7-7 with a 5.81 ERA (5.23 FIP), a 1.423 WHIP, and a 1.87 K/BB.

Esteban Loaiza, 2004

To say the Yankees’ rotation in 2004 was suspect would be an understatement. They replaced Clemens, Pettitte, and David Wells with Javier Vázquez, Kevin Brown, and Jon Lieber. In hindsight, this was one of the first times that Brian Cashman tried to build a rotation by trading for a young, cost-controllable pitcher with a lot of potential (Vázquez), an older ace that could break down at any moment (Brown), and a player returning from a major injury (Lieber). For those of you who remember the 2004 season, as I do, you remember that this plan, perhaps unsurprisingly, backfired (though Lieber did his part).

Although they tried to pry Randy Johnson from the Diamondbacks to reinforce the rotation, the Yankees turned to the 2003 Cy Young runner-up, sending José Contreras to the Chicago White Sox for the 32-year-old righty. Despite returning closer to his previous career norms, Loaiza was expected to be a consistent innings-eater for the pitching-starved Yankees, who were overtaxing their bullpen at an alarming rate (gee, doesn’t that sound familiar?).

Alas, to call Loaiza’s performance as a Yankee “garbage” would be an insult to the food that raccoons eat. After just five starts, he collected 20 earned runs in just 24 innings (a 7.30 ERA), and opposing batters had a .976 OPS against him. Not surprisingly, that got him yanked from the rotation, and he would make only five appearances in the final month of the year, including giving up three runs to close out a 22-0 loss to Cleveland on August 31st.