12/10 From 1986: Rodriguez-Bastaro; Paulino-Jaramillo; Nicasio, Ward, Acevedo, Sveum, Pena, Redus Signed; Soriano, Oviedo Drafted; Bell Bolts; No Deals; GIBBY's; HBD Pedro

• 1986 - SS Pedro Florimon was born in La Romana, Dominican Republic. Pedro turned a good glove into a seven-year MLB career, starting for Minnesota in 2013, but his bat has relegated him to mainly a journeyman depth guy. In his two seasons with Pittsburgh (2015-16), he mostly stayed busy in AAA while getting into 42 games with the Pirates, hitting just .149 over that span. P-Flo appeared with the Phils in 2017-18, his last MLB stop. 
• 1987 - GM Syd Thrift came home from the winter meetings empty-handed after trying to pry a corner infielder loose. Third baseman Brook Jacoby of the Indians was on his radar, but that deal never gained traction. Cleveland wanted a frontline hurler, and Doug Drabek, Mike Dunne and Brain Fisher were Pirates untouchables. Syd was also looking at 1B Bill Schroeder of the Brewers, in exchange for one of Mike Bielicki/Bob Kipper and a minor leaguer, then expanding the deal to include both if Milwaukee would include a minor league outfielder (one of Greg Vaughn, Darryl Hamilton or Lavell Freeman). It was just as well; Jacoby and Schroeder never came close to matching their 1987 career years again. 
• 1990 - OF/1B Gary Redus, 34, signed a two-year contract w/an option year for $1.425M after spending 1988-90 as a Bucco role player. He hit .250 in his two guaranteed campaigns, his option wasn’t exercised and he closed out his career with two final years in Texas. 
• 1992 - The Pirates signed 32-year-old RHP Alejandro Pena to a one-year/$1.35M contract. He had a strong four-year run before tendonitis laid him low in 1992, and the Bucs were counting on him to bounce back and solidify the back end of their pen. No such luck; he ended up with elbow surgery and missed all of 1993 (although he did voluntarily restructure the guaranteed money) and didn’t have much going in ‘94, when he was released after posting a 5.02 ERA. He finished his 15-year career in 1996 after stints with Boston, Atlanta and Florida. 

Alejandro Pena - 1994 Collectors Choice

• 1999 - Dale Sveum was signed as a free agent. He played three seasons for the Pirates (1996-97, 1999/.260 BA), and also managed at Altoona from 2001-03, winning an Eastern League Manager of the Year award before landing big league skipper jobs with the Brewers and Cubs. He was Kansas City’s bench coach through 2019, then joined their scouting staff. 
• 2000 - In a day they came to rue, the Pirates signed free agent OF Derek Bell of "Operation Shutdown" fame to a two-year contract worth $9.75M. Bell left the team during camp in 2002 after hitting .173 in his first campaign and never played in the majors again. He let it be known, after being told he had to earn a starting spot, that “I'm going into 'Operation Shutdown.' Tell them exactly what I said. I haven't competed for a job since 1991.” Bell left the team on March 29th and was released on March 31st rather than compete. The Pirates paid him $4.5M to go away when they cut him; Bell just moved onto his yacht and sailed into the baseball sunset. 
• 2003 - The Bucs signed veterans OF/1B Daryle Ward and RHP Juan Acevedo to minor league deals. Ward would get $600K and Acevedo $475K if they made the MLB roster, with both having a boatload of performance bonuses. Ward played until late July before a wrist injury laid him up, hitting .249 w/15 HR, and returned for 2005. For Acevedo, it was the end of an eight-year ride in the bigs. He spent part of the year in AAA Nashville and then Juan finished his career tossing for Monterey in the Mexican League. 
• 2008 - The Pirates pulled off a swap of teetering catchers, trading Ronny Paulino to the Philadelphia Phillies for Jason Jaramillo. Paulino and manager John Russell weren’t on each other's Christmas card list after JR decided to go with Ryan Doumit as the everyday catcher, and Jaramillo had impressed Russell from his days as the Phils AAA manager. The change of scenery didn’t particularly help either player (or team). Ronny played for four more years, never sniffing 100 games/season, and hit .265 over that span while JJ caught three seasons for the Bucs with a .235 BA in 119 games, which ended up his only MLB tour of duty. 

Jason Jaramillo - 2009 Topps Gold

• 2013 - Pittsburgh took three GIBBY (Greatness In Baseball Yearly awards): RHP Mark Melancon won the set-up player of the year, LHP Francisco Liriano took home the comeback player honors, and the Pirates were selected as the storyline of the year for their playoff run. 
• 2014 - The Pirates traded minor league LHP Joely Rodriguez to the Phillies for LHP set up man Antonio Bastardo. It was a domino effect deal, with Bastardo filling a hole in the bullpen created after southpaw Justin Wilson was traded to the Yankees. Bastardo put up a 4-1-1/2.98 slash in 66 Pirate outings while Rodriguez was removed from the Phil’s 40 man roster and assigned back to the minors after a rough 2015 AAA season. The Pirates lost Antonio to free agency in 2016, but brought him back to town in a deadline deal. He went 3-0/4.13 in his second coming before the wheels came off in 2017 and he was released with the Pirates eating the remainder of his $6.625M contract. He didn’t pitch in 2018 after a 140-game PED suspension, his second slap, and hasn’t had an MLB gig since. Rodriguez returned in 2020 and has tossed for the Rangers, Yankees and Mets during the 2020-22 seasons, signing with Boston for 2023. He’s been injury-bitten and the Red Sox didn’t pick up his ‘24 option, making him a free agent. 
• 2015 - The Bucs signed free agent RHP Juan Nicasio, who spent 2015 in the LA Dodgers' bullpen (1-3-1/3.86), to a one-year/$3M contract, with an arb season remaining for 2017. After a spotty stint in the rotation (5-5/5.05), Juan returned to the pen where he was 5-2 with a 3.88 ERA. To make room on the roster, the Pirates DFA’ed former #1 pick (fourth overall) of 2009, C Tony Sanchez, who played over parts of three seasons in 51 games, hitting .259. Nicasio had a strong 2017 campaign working exclusively from the pen (2-5-2/2.85), but the Pirates lost him, with no return, by placing him on irrevocable August waivers after passing up an earlier chance to move him on revocable waivers because he had been claimed by “a direct competitor” per GM Neal Huntington. Philly picked him up and quickly flipped him to the Cards, which may or may not have been that competitor, for a prospect. He spun for three more teams in the ensuing three seasons, and 2020 was his last MLB campaign, working a couple of brutal outings with Texas. 

Juan Nicasio - 2016 image/Positively Pittsburgh

• 2020 - Pittsburgh used the first pick in the Rule 5 Draft to select RHP Jose Soriano, 22, from the Angels. He had TJ surgery in February and wasn't expected to be ready for action until at least May, 2021. The Pirates also reeled in RHP Luis Oviedo, 21, from Mets for cash or a PTBNL; New York got Oviedo from the Indians in today's lotto before flipping him. MLB Pipeline rated Oviedo as the organization’s 20th best prospect and Soria as 21st. Those two additions filled the Pirates 40-man roster. Oviedo made the team, even with injuries and big-league struggles, but was waived in 2002. Cleveland claimed him and released him at the end of this season. Soriano was returned to the Halos at the end of the year after undergoing a second elbow procedure and made his MLB debut in 2023.