- 1959 – Vern Law became the first Bucco to sign a 1960 contract, agreeing to a deal that jumped his salary from $22,000 to an estimated $30K. Law had a breakout campaign in 1959, slashing 18-9/2.98 in 33 starts, going on to post 20 victories in 1960 while collecting the Cy Young Award and an All-Star spot.
- 1961 - The Pirates shipped minor league OF/1B Tom Burgess to the Angels for C Don Leppert. Leppert spent two seasons as a backup in Pittsburgh, while the persistent Burgess, whose only prior MLB action was in 1954 with the Cards (he signed with them as an 18-year-old in 1946), got to swing it off the bench with Los Angeles. Sadly, he didn’t get past the Mendoza Line either season and hung ‘em up after a final year in the minors.
|Don Leppert – 1962 Topps|
- 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. Afterward, Art scouted, coached and managed the Astros (1989–93), Oakland Athletics (1996–2002), and New York Mets (2003–04).
- 1984 – The Bucs traded LHP John Tudor and OF Brian Harper to the St. Louis Cardinals for UT Steve Barnard and OF George Hendrick. Tudor won 21 games with the Cards while tossing 10 shutouts the next season and won two World Series games. “Jogging George” hit .230 and lasted until August, when he was sent to the California Angels. Barnard never made it out of A ball.
- 1985 – Jim Leyland completed his staff with the hires of Bill Vidon (hitting coach), Mick Kelleher (1B coach) and Rich Donnelly (bullpen coach). They joined Gene Lamont (3B coach) and Ron Schueler (pitching coach) as members of Leyland’s first Pirates brain trust.
- 1991 – Jim Leyland and Bobby Bonilla got into a verbal spat when the skipper said he didn’t believe Bo, who went to the Mets, was ever planning to re-sign with the Pirates, prompting an exchange of “cheap shot” charges between the pair, with Bobby Bo countering with the charge that Pirates never negotiated in good faith.
|Jose Osuna – 2018 Topps Black|
- 1992 – UT Jose Osuna was born in Trujillo, Venezuela. He made his MLB debut with the Buccos in 2017, and in four years of bouncing around, he hit .241 w/24 HR in 660 ABs. The Pirates worked third base and the corner outfield into his resume while he hit .264 w/10 HR in 2019. He faded off the bench in 2020 and moved on to Japan. After a solid ‘21 campaign, Joey O signed a guaranteed three-year deal with Japanese League champs, the Tokyo Yakult Swallows.
- 2004 – Pittsburgh was on the verge of a deal with Colorado for C Charles Johnson, but it fell through when Johnson wanted an extra year added to his contract. The Bucs shifted gears and four days later, they traded for Benito Santiago instead. He caught six games before he was released, not that Johnson would have been much of an upgrade – 2005 was his last MLB season, too. He lasted just 19 games with Tampa Bay, hitting .196. The club ended up using Humberto Cota, Ryan Doumit and David Ross during the campaign with Ronny Paulino on the horizon.
- 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; Gonzo was traded in January and Gerut was cut during camp.
- 2008 - The Pirates signed 32-year-old IF Ramon Vazquez during the winter meetings to a two-year deal worth $4M after he had hit .290 for the Rangers. Alas, he batted .230 in 2009, then was released the following April, ending his nine-year MLB career while the Pirates ate $2M in salary.
|Matt Capps – 2006 Fleer Tradition Rookie Card|
- 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, ending his career. He’s now a part-time broadcaster for AT&T SportsNet.
- 2011 – The Milwaukee Brewers traded 3B Casey McGehee to Pittsburgh for RHP Jose Veras with the dominoes falling after the Brew Crew signed FA Aramis Ramirez. Veras put together a workmanlike campaign for Milwaukee while McGehee hit .230 and was swapped to the NYY for RHP Chad Qualls at the deadline. Casey went on to trip the light fantastic afterward, playing ball in the bigs, AAA and Japan in 2017, returning to the Nippon League in 2018 to end his career.
- 2012 - The Pirates signed free agent reliever Jason Grilli to a two-year/$6.75M contract. Grilli, who found a home in Pittsburgh after being taken from AAA Lehigh in 2011, was supposed to have turned down a larger deal with the Jays to remain a Bucco. Good move; he became the closer in 2013 after Joel Hanrahan was dealt, saved 33 games and made his first and only All-Star game. The wheels fell off next season and he was flipped to the Angels at the deadline.
- 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. He tossed in the playoffs for the Jays and then worked the postseason in 2017 with the Astros, taking home a WS ring, before moving to Detroit in 2018 and returning to the Buccos the following campaign. Frankie then signed with Philly, but ended up opting out of the 2020 season.
|Charlie Morton – 2014 Topps|
- 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. It worked out for Charlie, too – in 2017, he went 14-7 for Houston and beat the Yankees in the ALCS and the Dodgers in the WS, and followed with strong campaigns in 2018 & ‘19 (w/Tampa Bay) before moving on to Atlanta. Whitehead tossed to a 7.52 ERA at Altoona and Bristol, and the Bucs released him; he hasn’t worked pro ball since.
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