- 1975 - Houston sent veteran IF Tommy Helms to the Pirates for a PTBNL (IF Art Howe). Helms was at the end of his days here, while Howe went on to have a solid career with the Astros and Cards, playing for 11 years with a .260 career BA.
- 1984 - The Bucs traded LHP John Tudor and OF Brian Harper to the St. Louis Cardinals for UT Steve Barnard and OF George Hendricks. Tudor won 21 games with the Cards while tossing ten shutouts the next season and won two World Series games. Hendricks hit .230 and lasted until August, when he was sent to the California Angels. Barnard never made it out of A ball.
|Grabow made the cut - 2009 Upper Deck|
- 2006 - The Pirates had a class of eight arb-eligible players and tendered them all. They were IF’s Freddy Sanchez & Jose Castillo, OF’s Xavier Nady & Jody Gerut, and hurlers Mike Gonzalez, John Grabow & Shawn Chacon along with C Humberto Cota. Six stuck with the team; Gonzalez was traded in January and Gerut was cut during camp.
- 2008 - The Pirates signed IF Ramon Vazquez, the only player with major league experience added to the roster during the winter meetings, to a two-year deal worth $4M. He hit .230 in 2009, then was released the following April, ending his nine-year MLB career with the Pirates eating $2M in salary.
- 2009 - The Bucs non-tendered RHP Matt Capps, allowing the closer to walk as an uncompensated free agent. He signed a one-year deal with Washington for $3.5M and became an All-Star. Capps then went to the Twins and closed, but shoulder inflammation derailed him there in 2012, and a year later he had surgery. He hasn’t pitched in MLB since that time.
|Frankie gets his - 2014 Bowman Silver Ice|
- 2014 - The Pirates officially announced Francisco Liriano’s three-year, $39M contract, the biggest FA contract in franchise history, after Frankie passed his physical. The financial terms of the deal were: $2M signing bonus, $11M in '15, $13M in '16, $13M in '17 plus sundry bonuses. The free agent had been 2014’s opening-day pitcher for the Bucs, winning 23 games in 2013-14 for the Bucs. He went 41-36, 3.67, during his four campaigns with Pittsburgh with 659 K in 623+ IP before being moved to Toronto.
- 2015 - Pittsburgh sent RHP Charlie Morton to the Phils for minor league RHP David Whitehead. Charlie was one of the league’s better ground ball pitchers (55.3% in his career), earning him the nickname “Ground Chuck,” but was often hurt and underperformed as a Bucco, though he possessed some great stuff. In seven seasons with Pittsburgh, he went 41-62/4.39 and never made 30 starts in any single campaign. The move was made to free up some money for the 2016 season; Morton was due $8M in 2016.