- 1987 - The Pirates traded RHP Don Robinson to the San Francisco Giants for C Mackey Sasser. The Giants turned Robinson into a starter the next season and he became a rotation pitcher for the next three years while Sasser was flipped to the Mets in 1988, where he had a long run as a back-up catcher.
- 1993 RHP Jon Lieber was traded by the Kansas City Royals along with reliever Dan Miceli to the Bucs for closer Stan Belinda.
- 2001 - The Pirates traded the well-traveled LHP Terry Mulholland to the Dodgers for pitchers Mike Fetters and Adrian Burnside. Mulholland, from Uniontown, pitched for 11 teams in a 20 year career, and had a pair of stints with the Cubs, Phils and Giants. The FO also swapped Mike Williams to the Astros for RHP Tony McKnight. It was actually more like a lend-lease, as Williams signed with the Bucs again as a free agent after the season.
- 2002 - The Bucs sent first round bust OF Chad Hermansen to the Cubs for OF Darren Lewis, who refused to report to the Pirates and retired instead.
|Chad Hermansen 2001 Upped Deck series|
- 2003 - Pitchers Brandon Lyon, Anastacio Martinez and Jeff Suppan were traded by the Bucs to the Red Sox for LHP Mike Gonzalez, 2B Freddy Sanchez and cash. Originally, Gonzalez had gone to Boston for Lyons and Martinez a few days earlier, but Lyons had an iffy physical causing a reworking of the deal. The mulligan panned out pretty well for the Bucs.
- 2004 - GM Dave Littlefield reportedly rejected an offer to deal pitcher Kris Benson to the Phillies for a power-hitting prospect named Ryan Howard, who would eventually become a NL MVP. The Bucs thought they had a Howard clone already in their system with Brad Eldred.
- 2005 - The Cubs sent young OF Jody Gerut to Pittsburgh for vet OF Matt Lawton. The Cubs shipped Lawton to the Yankees for a minor leaguer in August. Gerut, hampered by a bum knee, barely played and was released after 2006, appearing in just four games as a Pirate.
- 2006 - Busy at the deadline: The Pirates traded pitchers Roberto Hernandez and Oliver Perez to the Mets for Xavier Nady. Pittsburgh also sent P Kip Wells to the Rangers for P Jesse Chavez, traded OF/1B Craig Wilson to the Yankees for P Shawn Chacon and acquired RHP Brian Rogers from the Detroit Tigers in exchange for 1B Sean Casey.
|Sean Casey - Pirate Promo|
- 2007- The Bucs traded OF Rajai Davis and IF Stephen McFarland to the San Francisco Giants for RHP Matt Morris, who was being paid $7.5M in 2007 and under contract to make $9.5M in 2008 with a $1M buyout for 2009. He was released on April 27th of 2008 after going 3-8 with a 7.04 ERA in 16 Pirate starts. Many believed this deal was the straw that broke the back of GM Dave Littlefield’s era in Pittsburgh.
- 2008 - Jason Bay and Josh Wilson were traded to the Boston Red Sox in a three team deal that sent Manny Ramirez to the Los Angeles Dodgers and Andy LaRoche with Bryan Morris to the Pirates from LA, with Brandon Moss and Craig Hansen coming to the Bucs from Beantown. None of the prospects panned out for Pittsburgh, and Bay’s career was hamstrung by injury. Speculation was that Tampa Bay was very much interested in dealing and offered SS Reid Brignac & P Jeff Niemann for Bay, but the Bucco FO wanted Wade Davis instead of Niemann.
- 2010 - A lot of dealing: RHP James McDonald was traded to Pittsburgh with OF Andrew Lambo by the LA Dodgers for RHP Octavio Dotel and cash. The Bucs also flipped LHP Javier Lopez to the Giants for RHP Joe Martinez and OF Joe Bowker. In a house cleaning & change of scenery deal, SS Bobby Crosby, RHP D.J. Carrasco and RF Ryan Church were sent to the Arizona Diamondbacks for cash, C Chris Snyder and SS Pedro Ciriaco.
|DJ Carrasco (photo Getty Images)|
- 2011 - OF Ryan Ludwick was sent to the Pirates by San Diego for cash. He hit .232 with two homers during the stretch run and then signed with the Reds in the off season.
- 2012 - 1B Gaby Sanchez and RHP Kyle Kaminska went from the Marlins to the Pirates for OF Gorkys Hernandez and 2013’s sandwich compensation draft pick five minutes before the deadline expired. Before that trade, the Bucs dealt 3B Casey McGehee to the Yankees for RHP Chad Qualls.