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.