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25 Smartest Moves of the Past 25 Years: Yankees trade for Bobby Abreu

The Yankees committed highway robbery when they acquired Abreu in 2006.

Toronto Blue Jays v New York Yankees Photo by Chris McGrath/Getty Images

The 2006 Yankees lineup was quite deep. Of the seven players who made at least 500 plate appearances, only one had an OPS+ below the league average 100. They had the reigning AL MVP in Álex Rodríguez, and a guy who came very close to winning MVP (and arguably should’ve) that season in Derek Jeter.

That’s not to say there weren’t holes, however. Due to injuries and a lack of production in general, one of those holes was in right field. As it just so happened, a pretty good right fielder was available, and would end up helping the Yankees to a ninth straight AL East crown.

Trade Details: Bobby Abreu, Cory Lidle to Yankees; C.J. Henry, Jesus Sanchez, Carlos Monasterios, and Matt Smith to Phillies

Transaction Date: July 30, 2006

Career NYY Stats (2006-08): 372 games, 1,631 PA, .295/.378/.465, 43 HR, 243 RBI, 6.7 fWAR

Going into the 2006 season, Gary Sheffield was set as the right fielder in the final year of the three-year deal he had signed ahead of the 2004 season. He started off the ‘06 season in excellent form, hitting .341/.390/.517 through April 29th. However on that day, he collided with Shea Hillenbrand at first base, injuring his wrist. He attempted to play through it over the course of May, but it eventually became clear that Sheffield would need to undergo surgery, keeping him out for a couple months.

In his absence, the Yankees tried a couple different players in right, including Bernie Williams in what would be the final season of his career. While Williams ended up putting up only slightly below league average numbers, there really wasn’t anyone lighting things up out in right. That’s why when an opportunity arose right near the trade deadline, the Yankees took it.

Meanwhile in Philadelphia, the Phillies had gotten off to a slow start in 2006. Despite a July 29th win over the Marlins, the Phillies sat at just 47-54, 14 games back of first in the NL East. After that start, GM Pat Gillick decided to tear things down a bit, and apparently decided that right fielder Bobby Abreu was one of the expendable pieces.

At 33, Abreu was a bit older than the Phillies’ up-and-coming core that included the likes of Chase Utley, Jimmy Rollins, and eventual ‘06 NL MVP Ryan Howard. However, in 2002, Abreu had also signed a five-year, $64 million dollar contract extension that included a full no-trade clause. He reportedly would only waive said clause for a few teams: the Yankees, Mets, Red Sox, and Angels.

With the Yankees in need of a right fielder and arguably at the height of the late George Steinbrenner free-spending era, the Yankees agreed to take on the majority of the rest of Abreu’s contract. The outfielder agreed to waive his contract, and Abreu became a Yankee on July 30, 2006.

In exchange, the Yankees sent prospects C.J. Henry, Jesus Sanchez, Carlos Monasterios, and Matt Smith to the Phillies. Smith had seen time with the Yankees earlier that season, throwing 12 innings out of the bullpen. However, the seemingly big prize for the Phillies in the deal was Henry, then the Yankees’ No. 4 prospect according to Baseball America. The Phillies had reportedly wished to acquire top prospect Phil Hughes in the deal, but the Yankees balked at that before the teams eventually settled on the deal. The trade was bemoaned in Philadelphia, with one columnist calling “The Great Gillick Giveaway.”

In addition to Abreu, the Yankees also got pitcher Cory Lidle in the deal, looking to bolster the back end of a rotation that had Chien-Ming Wang, Mike Mussina, and not much else.

In Abreu’s first game as a Yankee, he drew a walk in a 5-1 win. The plate discipline would be a recurring theme. Over his the rest of his ‘06 as a Yankee, Abreu drew 33 walks in 58 games. Add that to the 91 he had drawn earlier in the season as a Phillie, and he finished with an MLB-leading 124 for the season. In general, Abreu showed remarkable discipline at the plate. In his 248 plate appearances that season, he saw over 4.4 pitches per plate appearance. His .419 on-base percentage fit in perfectly in the #3 spot in the lineup, where he was used most.

After the final game the Yankees played without Abreu, the team was 61-41, and a half-game back of the Red Sox in the AL East. Over the rest of the season, the went 36-24 and finished with a comfortable 10 game cushion. They did infamously lose in the ALDS to the Tigers, but Abreu acquitted himself well in postseason play for the first time, putting up an .812 OPS.

Following 2006, Abreu spent another two seasons with the Yankees and continued putting up good numbers, getting on base, and seeing a lot of pitches. He got down-ballot MVP votes in 2007 as the Yankees surged late to win a Wild Card spot, and was the last ever person to record a stolen base at the old Yankee Stadium in 2008. However, the Yankees fell short in both seasons, getting eliminated by Cleveland in four games in the ‘07 ALDS before missing the playoffs entirely in ‘08. With the Yankees focusing their free agent pursuits elsewhere, Abreu signed with the Angels in 2009, ending his Yankee career.

As for the Yankees’ prospect cost, it ended up being not much. Henry, the key piece of the deal, was out of baseball within a couple years, and ended up playing college basketball at Kansas. Smith threw just 12.2 innings for the Phillies. Monasterios didn’t make the majors until 2010 with the Dodgers, while Sanchez didn’t make it at all.

When you look at the greatest trade swindles off all time, the Bobby Abreu to the Yankees trade is a pretty strong nominee.