Pittsburgh Pirates History: Revisiting the 2008 Trade with the Yankees

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The Pittsburgh Pirates have made quite a few trades with the Yankees over the years. Some good deals, some bad deals, and some in between.

In 2008 the Pittsburgh Pirates were in a very similar situation as they have been in the last few recent years. The team was rebuilding and in full sell mode. They looked to trade off as much veteran talent as they had and to get as much prospect talent back as possible.

This led to one of the biggest trades of the 2008 Trade Deadline. The Pittsburgh Pirates had some interesting talent on the team but they were never able to play winning baseball. The team would trade star outfielder Jason Bay in a blockbuster deal that stole the headlines for the day. Bay went to the Red Sox and Manny Ramirez was sent to the Dodgers with prospects coming back to Pittsburgh.

However, there was another pretty significant move that the Bucs made at that Trade Deadline. They would link up with the Yankees for a 6 player deal. The Bucs would send outfielder Xavier Nady and relief pitcher Damaso Marte to New York. Again, an expected deal at the time with both players having really strong years at the time and were pending free agents.

In return, the Bucs received multiple players who would stick around for a bit. Coming back in the deal were pitchers Ross Ohlendorf, Daniel McCutchen, and Jeff Karstens. Meanwhile, the primary prospect in the deal was a highly touted outfield prospect, Jose Tabata.

Yes, the player who would become known as “Neck Lips” due to his tattoo. The player who would break up Max Scherzer’s perfect game bid in 2015. However, he is also the player who would represent many of Huntington’s failed moves. Not only did he acquire him as the main piece of a deal, but he also would give him a 6-year contract extension worth north of $30 million.

All in all the trade was a bust for the Pittsburgh Pirates. Daniel McCutchen and Ross Ohlendorf did not turn into big parts of this team’s future. Karstens was serviceable, but not stellar. Tabata was basically a complete bust, never posting an OPS above .760 and missing games due to injury.

The trade was not much better for the Yankees. Nady would have a strong finish to the 2008 season and would earn a contract back with the Yankees in 2009. Unfortunately, Nady would miss most of the season due to a career-altering 2nd Tommy-John Surgery.

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The Bucs traded Marte at the right time as he posted an ERA over 5 with the Yankees down the stretch. He would stick around for a few more seasons with the Yankees but never replicate the success he had here in Pittsburgh. The deal was essentially a wash for both clubs, the Yankees would miss the playoffs in 2008 and the Bucs really did not get much out of the 4 prospects acquired.

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The Pittsburgh Pirates have made quite a few trades with the Yankees over the years. Some good deals, some bad deals, and some in between.

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