- 2000 - The Bucs got SS Jack Wilson from the Cards in exchange for LHP Jason Christiansen. Wilson was the starter at short when healthy from 2001 until he was traded in 2009, and won a Gold Glove and All-Star berth in 2004.
|Jack Wilson 2002 Fleer Tradition series|
- 2001 - The Bucs sent RHP Jason Schmidt and OF John Vander Wal to the Giants for OF Armando Rios and RHP Ryan Vogelsong. Schmidt went 7-1 the rest of the year for SF and then signed a big four-year contract. Vogelsong underwent Tommy John surgery two months later.
- 2004 - The Pirates traded RHP Kris Benson and IF Jeff Keppinger to the Mets for 3B Jose Bautista (who they had lost in the 2003 Rule 5 draft), IF Ty Wiggington and RHP Matt Peterson. Bautista became the tenth major leaguer to play for four teams in a season, having been on the rosters of Baltimore, Tampa Bay and Kansas City. In fact, he was actually on five teams, as he was acquired by the Mets from the Royals but sent to Pittsburgh the same day.
|Joey Bats 2002 Topps rookie card|
- 2009 - The Pirates shipped lefties Tom Gorzelanny and John Grabow to the Cubs in exchange for IF Josh Harrison and RHPs Kevin Hart & Jose Ascanio.
- 2011 - The Pirates traded minor league 1B Aaron Baker to the Orioles for 1B Derrek Lee, the first time that Pittsburgh was a buyer at the trade deadline since dealing for SS Shawon Dunston in 1997 to bolster the “Freak Show” lineup.
- 2012 - In a trade of 2006 first rounders, Pittsburgh sent RHP Brad Lincoln to Toronto for OF Travis Snider. Lincoln is back in the organization while Snider was traded to Baltimore in 2015 for a pair of prospects.
- 2015 - The Pirates acquired veteran RHP Joe Blanton, 34, from the Royals for cash after he had been DFA’ed. Blanton posted a 3.89 ERA in 15 games (4 starts) with KC in 2015.