- December 16, 1938 - The Boston Bees traded catcher Ray Mueller to the Pirates for C Al Todd and OF Johnny Dickshot. Todd had a couple of good seasons left, while Dickshot wouldn’t hit his prime until his last two seasons in 1944-45 during the war for the White Sox. Iron Man Mueller was 38, and played a year in Pittsburgh as a reserve catcher, hitting .269.
- December 16, 1956 - Coach Rick Sofield was born in Cheyenne, Wyoming. He was an outfielder for the Twins, worked in the minors (he was the Pirates' minor league field coordinator in 2002) and managed in college. Sofield was brought on staff by long-time bud Clint Hurdle in 2011.
- December 16, 1960 - The Bucs sent UT Harry Bright, 1B RC Stevens and RHP Bennie Daniels to the expansion Washington Senators (now the Texas Rangers) for veteran RHP Bobby Shantz. Daniels was a useful starter in DC for several seasons, while Shantz lasted a year in Pittsburgh before being lost to the Houston Colt .45s in the 1961 expansion draft. He went 6-3-2/3.22 in 43 games with the Pirates, and pitched fairly effectively afterward, his career lasting until the end of the 1964 season.
Topps series 1961
- December 16, 2004 - The Pirates acquired C Benito Santiago and cash from the Royals for RHP Leo Nunez (Juan Oviedo). The 30 year old Oviedo served a 2012 suspension after pitching for seven seasons because of name fraud; he went by Nunez to gain a later birthdate. Santiago got in six games before his release and never played in the majors again.
- December 17, 1883 - CF Ennis “Rebel” Oakes was born in Lisbon, Louisiana. He played five years for the Reds and Cards, then jumped to the Federal League when it was established in 1914. After two seasons as the player-manager for the Pittsburgh Rebels, named in his honor, the league folded and Rebel never returned to MLB despite his .295 BA as a Rebel.
- December 17, 2010 - RHP Kevin Correia signed as a FA with Pittsburgh, agreeing to a two year, $8M deal. In those two seasons, he would post a line of 24-22/4.49 before moving on to Minnesota.