- 1899 - Barney Dreyfuss traded a dozen players from the Louisville Colonels to Pittsburgh (Jack Chesbro, George Fox, Art Madison, John O'Brien and $25,000 went to Louisville for Fred Clarke, Bert Cunningham, Mike Kelley, Tacks Latimer, Tommy Leach, Tom Messitt, Deacon Phillippe, Claude Ritchey, Rube Waddell, Jack Wadsworth, Honus Wagner and Chief Zimmer, with Chesbro getting assigned back to Pittsburgh for the 1900 season). He then took over the Pirates after the deal, in effect transferring the core of his old team to his new one. They became one of the powerhouse clubs of the early 1900's thanks to the greatest deal ever swung by the Buccos.
- 1937 - C Jim Pagliaroni was born in Dearborn. “Pags” caught for the Bucs from 1963-67, sometimes starting and sometimes in platoon. He hit .254 during his Pittsburgh time and still has the record for most homers hit by a Pirate catcher in a season at 17, set in 1965. Injuries and reports that he wanted to be traded - he was playing in a rotation with Jerry May and Jesse Gonder - resulted in his contract being sold to Oakland in 1967.
|Jim Pagliaroni 1967 Topps|
- 1939 - RHP Bill Swift was traded, along with cash, to the Boston Bees for RHP Danny MacFayden. Swift had won 91 games for the Bucs in eight years and MacFayden 124 in his career, but both were at the end of the road and the deal ended up a wash.
- 1947 - In a what-were-they-thinking move, the Pirates traded IF Billy Cox, IF Gene Mauch and P Preacher Roe to the Brooklyn Dodgers for P Hal Gregg, P Vic Lombardi and OF Dixie Walker. None of the former Dodgers lasted past 1950 in Pittsburgh, while Cox and Roe would become mainstays in Brooklyn. The impetus for the deal was reportedly provided by Walker, who didn’t want to play with Jackie Robinson at the time, but was to later salute his talents. Dixie was the key to the deal;, but he played just one year, hitting .318, and then retired.
- 1948 - The Bucs traded IF Frankie Gustine and RHP Cal McLish to the Chicago Cubs for LHP Cliff Chambers and C Clyde McCullough. Gustine was a three-time All Star for Pittsburgh at the end of his career; he would later open an Oakland restaurant on Forbes Avenue a few steps from Forbes Field. McLish would go on to win 92 games in the next 11 years, including 19 for Cleveland in 1959. The Pirates unloaded Chambers the following year, while McCullough spent four years in Pittsburgh, batting .258.
|Clyde McCullough 1949 Bowman|
- 1977 - The Pirates were part of a Rube Goldberg four-team deal that worked out pretty well for them: The Bucs sent OF Al Oliver and SS Nelson Norman to the Texas Rangers. The Atlanta Braves sent 1B Willie Montanez to the New York Mets. The Texas Rangers sent P Tommy Boggs, P Adrian Devine and OF Eddie Miller to the Atlanta Braves, OF Ken Henderson and OF Tom Grieve to the New York Mets, and P Bert Blyleven to the Pirates. The New York Mets sent P Jon Matlack to the Texas Rangers and 1B/OF John Milner to Pittsburgh. From Pittsburgh’s standpoint, they traded Oliver and Norman for Blyleven and Milner.
- 1992 - The Barry Bonds era ended after playing seven seasons in Pittsburgh when he signed a FA contract with the San Francisco Giants worth a then-record $43.75M over six years, turning down a five year/$36M offer from the Yankees. Bonds' contract with the called for a $2.5-million signing bonus and yearly guarantees of $4 million, $4.75 million, $7.75 million, $8 million, $8.25 million and $8.5 million. His sweeteners were a hotel suite when the team was on the road, bonuses for postseason awards and $500,000 deferred from each year's salary at 9% interest, starting in 1999.
- 2003 - The Bucs declined to offer salary arbitration to a boatload of players: P Julian Tavarez, OF Reggie Sanders, OF Matt Stairs, IF Pat Meares, IF Pokey Reese and IF Jeff Reboulet. None were brought back by the team.
|Matt Stairs 2003 Topps Gold|
- 2005 - The Reds traded 1B Sean Casey to the Pirates for LHP David Williams. “The Mayor” (he picked up the title in Cincinnati, where he was so popular he could have been elected mayor) was beset by injuries, but hit .296 with three home runs and 29 RBIs in 59 games for his hometown Bucs (Casey graduated from Upper St Clair HS) before being moved to the Tigers at the deadline. Williams won five games over the next two seasons, had surgery for a herniated disk and never returned to the majors; Casey retired after the 2008 campaign.