- 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.
- 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 resulted in his contract being sold to Oakland.
- 1947 - In a what-were-they-thinking deal, 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; he played one more 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. 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.
1943 Play Ball Series; image from Baseball Almanac
- 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, the traded Oliver and Norman for Blyleven and Milner.
- 1992 - The Barry Bonds era ended when he signed a FA contract with the San Francisco Giants worth a then-record $43.75M over six years after playing seven seasons in Pittsburgh.
- 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.
- 2005 - The Reds traded 1B Sean Casey to the Pirates for LHP David Williams.