- 1961 - The Pirates shipped minor league OF/1B Tom Burgess to the Los Angeles 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 for the Angelinos in 1962-’63. Sadly, he didn’t bat his way above the Mendoza Line either season and hung ‘em up after a final year in the minors.
- 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 C/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. Harper was a late bloomer, but did break out in 1988 with the Twins. In his six years with Minnesota, he hit .306 with 111 homers and won a Fall Classic in 1991. “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 Virdon (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 dugout brain trust.
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| Jimmy in the news - 1988 Topps |
- 1991 - Jim Leyland and Bobby Bonilla got into a verbal spat when the skipper said he didn’t believe Bo, who went to the New York Mets, was ever planning to re-sign with the Pirates. That prompted an exchange of “cheap shot” charges between the pair, with Bobby Bo’s defense being that the Pirates front office never negotiated in good faith. A little bit me, a little bit you...
- 1992 - UT Jose Osuna was born in Trujillo, Venezuela. He made his MLB debut with the Buccos in 2017, and in his four years 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.
- 1997 - RHP Yerry De Los Santos was born in Samana, Dominican Republic. A Pirates Latino signee who started out in 2015 in the Dominican Summer League, the reliever steadily climbed the Pittsburgh minor league ladder. He had a strong 2021 campaign (3-2-2/1.52, AAA + AA) in the upper levels, then continued to be impressive (2-0/1.72) during the opening weeks of 2022 at Indy, getting his call to the show in mid-May. He slashed 0-3-3-/4.91, wearing down at the end - he gave up just seven runs in his first 22 outings, but seven more in his final four appearances, leading to a season-ending trip to the IL with a shoulder sprain. He pitched a split season in ‘23 between the Bucs and Indy, was removed from the 40-man roster at the end of the year despite a 1-1/3.33 slash in 22 outings and was signed by the New York Yankees as a free agent.
- 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.
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| Benny Santiago - 2005 Pirates promo card |
- 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 through the spring and into the campaign; 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.
- 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 radio/TV 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.
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| Casey McGehee - 2012 Topps Update |
- 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 only All-Star outing. The wheels fell off next season and he was flipped to the Angels at the deadline. His four-year Bucco line was 3-11-47/3.01 with 44 holds and 222 punch outs in 161-2/3 innings.
- 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. He agreed to an NRI with the Blue Jays in 2021, was released and opted for free agency but couldn’t find any other offers and sat out the campaign.
- 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. Philly reclaimed him, but let him go in 2017.
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