- 1980 – In the final Free Agent Re-Entry Draft, the Bucs John Milner opted out of contract to test the waters, but the Pirates managed to ink him to a new deal (they kept a retainer on his rights). The Bucs claimed bidding rights on a dozen players including Dave Winfield and Don Sutton, and signed none. But they did eventually get 1B/OF Willie Montanez, who they had on their list as a potential replacement if they had lost Milner. Willie signed with the Expos, but joined the Pirates in August when they traded The Hammer to Montreal.
- 1988 – Charlie Muse publicly announced his retirement from the Pirates in a Pittsburgh Press piece written by Bob Hertzel. Muse, 71, had worked for the Bucs since 1950 as a scout, ticket-office boss, Director of Operations for Three Rivers Stadium (1974-76) and finally as Travelling Secretary. Before that, he had managed Duquesne University’s nine, skippered in the minors, served in the Army twice, and was a driving force in the final design and more importantly, the players’ acceptance of the batting helmet.
|Doug Drabek – 1990 Poster|
- 1990 - RHP Doug Drabek, who posted a 22-6 record and a 2.76 ERA, was named the NL Cy Young winner and became the first Pirate since Vern Law in 1960 to take home the award. He received 23 of 24 first-place votes and 118 of a possible 120 points in balloting by the Baseball Writers Association of America. Left in the dust were Ramon Martinez of the Los Angeles Dodgers, who was second with the other first-place vote and 70 points, and Frank Viola of the New York Mets was third with 19 points. No other Bucco hurler has won the honor since.
- 1990 - After his walk year, OF RJ Reynolds was seeking a three-year/$4M deal to re-sign with Pittsburgh; the Pirates countered with a two-year/$1.5M offer. The situation was resolved by a third option: RJ signed a $1.3M contract with Yokohama of the Japanese League. It worked out OK for Reynolds; he got his three seasons, albeit in Japan, then spent his final campaign in Mexico before retiring at age 35.
- 1991 - 3B Steve Buechele, coming off a season hitting .262 w/22 HR & 85 RBI, rejected the Pirates contract offer for four-years/$10M after earning $775K during the ‘91 campaign. It was a career year for him, although most of his numbers were put up at Texas, as he hit .246 in 31 games as a Bucco after a deadline deal. But it worked out relatively well for him – he eventually signed for four-years/$11M. It didn’t prolong his Pittsburgh stay by much, though – he batted .249 in 80 games in 1992 and was shipped to the Cubs for LHP Danny Jackson in July.
- 1996 - The Pirates sent 2B Carlos Garcia, 1B/OF Orlando Merced and P Dan Plesac to the Toronto Blue Jays for P Jose Silva, IF Abraham Nunez, and OF Craig Wilson plus prospects SS Brandon Cromer, P Jose Pett and P Mike Halperin. Merced had four good seasons remaining, Plesac played through 2003 and Garcia, who was the Jays main target, ended up as a bench guy in the AL and lasted three more years in the show. Silva spent five years in Pittsburgh, but his ERA during that span was 5.44 (he was 24-28-4 for the Pirates), Wilson and Nunez were in and out of the lineup and the other players were minor league material.
|AJ Burnett – 2014 Topps|
- 2014 - RHP AJ Burnett returned to the Pirate flock, signing a one-year contract valued at $8.5M after a dismal season (8-18/4.59) in Philadelphia. He told the media that “This is where I want to finish my career, playing for this team and for this city. I want to win a ring, and I want to do it in Pittsburgh.” Burnett left $4.25M on the table for the reunion by turning down a player option worth $12.75M with Philadelphia to become a FA, and had his agent negotiate solely with the Pirates. AJ had pitched in 2012-13 for the Bucs, winning 26 games with a 3.41 ERA before moving across the state. He finished his swan song with another solid season, going 9-7/3.18 though slowed down by a late year injury. AJ also was named to his first All-Star team after 17 seasons in the show.
- 2018 - The Pirates sent OF Jordan Luplow and IF Max Moroff to the Cleveland Indians for IF Erik González and RHP’s Tahnaj Thomas and Dante Mendoza. Luplow, 25, a third-round pick in 2014 and Minor League PoY in 2017, had a chance to break camp with the Bucs in 2019 with Gregory Polanco injured while Moroff, also 25 & a 16th-round high school pick in 2012, had been bypassed on the Pirates depth chart. Both had auditioned with the big club. J-Lo hit .194 in 64 games in 2017-18 while Maxie batted .193 in 84 games played from 2016-18. Gonzalez (.263 lifetime BA) was out of options and expected to stick as a utility man who had played six positions for the Tribe, while the two pitchers were 19-year-old lotto tickets. Gonzalez had a solid September in a year mostly lost to injury and became a semi-regular SS/3B in 2020, but a subpar 2021 saw him sent to Indy and declaring free agency. Luplow proved to be a strong platoon guy while Moroff remained mainly in the minors as depth. Throw-in RHP Tahnaj Thomas had a promising year in rookie ball, spent 2020 in the Instructional League and was beaten up pretty well in Hi-A in ‘21 while Mendoza has yet to escape the Rookie League.
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