- 1976 - The Pirates traded OF Richie Zisk and RHP Silvio Martinez to the Chicago White Sox for pitchers Goose Gossage and Terry Forster. Except for minor-leaguer Martinez, the players were a year away from free agency, and all three took advantage to find new teams in 1978. But the big name rentals had a payoff: Zisk hit .290 with 30 homers and 101 RBI, and Gossage collected 11 wins, 26 saves and posted a 1.62 ERA with 10.2 K per nine innings. Both were named All-Stars.
|Bobby Bo 1987 Fleer|
- 1985 - Bobby Bonilla, who the Bucs signed out of high school in 1981, was taken by the Chicago White Sox in the Rule 5 draft. The Pirates got Bobby Bo back in July of the following year, but it cost them RHP Jose DeLeon. Syd Thrift had signed him as a scout and reeled him back in as GM. It was worth it - from 1986 to 1991, Bonilla had a .284 BA with 114 home runs and 500 RBI's. He also made the All-Star team four years in a row before leaving town.
- 1999 - Dale Sveum was signed as a free agent. He played three seasons for the Pirates (1996-97, 1999/.260 BA), and also managed at Altoona from 2001-03, winning an Eastern League Manager of the Year award before landing big league skipper jobs with the Brewers and Cubs.
- 2000 - In a day they came to rue, the Pirates signed free agent OF Derek Bell of "Operation Shutdown" fame to a two-year contract worth $9.75M. Bell left the team during camp in 2002 after hitting .173 in his first campaign and never played in the majors again. The Pirates paid him $4.5M to go away when they cut him; Bell just moved onto his yacht and sailed into the sunset.
|Ronny Paulino 2008 Topps Heritage|
- 2008 - The Pirates, in a swap of catchers, traded Ronny Paulino to the Philadelphia Phillies for Jason Jaramillo. The change of scenery didn’t particularly help either player (or team).
- 2009 - The Pirates signed FA IF Bobby Crosby to a $1M deal with another $500K possible in bonus money. He hit .224, was traded to Arizona and was out of baseball after 2010. He left the majors with a whimper, but entered baseball with a bang, having won the AL Rookie of the Year Award with Oakland in 2005.
- 2013 - Pittsburgh took three GIBBY (Greatness In Baseball Yearly awards): RHP Mark Melancon won the set-up player of the year, LHP Francisco Liriano took home the comeback player honors, and the Pirates were selected as the storyline of the year for their October run.
|Antonio Bastardo (photo Dave Arrigo/Pirates)|
- 2014 - The Pirates traded minor league LHP Joely Rodriguez to the Phillies for LHP setup man Antonio Bastardo. It was a dominoes effect deal, with Bastardo filling a hole in the bullpen caused when southpaw Justin Wilson was traded to the Yankees. Bastardo put up a 4-1-1/2.98 slash in 66 Pirate outings while Rodriguez was removed from the Phil’s 40 man roster and assigned back to the minors after a rough 2015 AAA season. The Pirates lost Antonio to free agency in 2016, but brought him back to town in a deadline deal. He went 3-0, 4.13 in his second coming.
- 2015 - The Bucs signed free agent RHP Juan Nicasio, who spent 2015 in the LA Dodgers' bullpen, to a one-year/$3M contract with an arb season remaining for 2017. After a spotty stint in the rotation (5-5, 5.05), Juan returned to the pen where he was 5-2 with a 3.88 ERA. To make room on the roster, the Pirates DFA’ed former #1 pick (fourth overall) of 2009, C Tony Sanchez, who played over parts of three seasons in 51 games, hitting .259.