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The first deal sent Xavier Nady and Dámaso Marte to the New York Yankees in exchange for minor leaguers José Tábata, Jeff Karstens, Ross Ohlendorf, and Dan McCutchen.
In the second deal, Huntington shipped Jason Bay to the Boston Red Sox in exchange for Brandon Moss, Andy LaRoche, Craig Hansen, and minor leaguer Bryan Morris.
Huntington made yet another move on July 22 by trading starting first baseman Adam LaRoche to the Red Sox for minor leaguers Argenis Diaz and Hunter Strickland.
Later that day, Huntington sent all-star second baseman Freddy Sanchez to the San Francisco Giants for highly regarded pitching prospect Tim Alderson.
After the season ended, Huntington acquired second baseman Akinori Iwamura from the Tampa Bay Rays in exchange for pitcher Jesse Chavez.
The 2010 season saw Pedro Alvarez, the club's top prospect and Huntington's 2008 first round draft pick, make his MLB debut, along with the emergence of other young talents, including José Tábata, Neil Walker, and Evan Meek.
On July 31, Huntington continued to reshape the Pirates roster by acquiring catcher Chris Snyder and shortstop prospect Pedro Ciriaco from the Diamondbacks in exchange for back-up veterans Ryan Church, Bobby Crosby, and reliever D. J. Carrasco.
Although the Pirates finished below .500 for another consecutive year, the team started the season strong and was in first place in the National League Central by the All-Star break.
Much of the success was attributed to good starting pitching performances by Huntington acquirees Jeff Karstens, Charlie Morton, James McDonald, and the newly signed Kevin Correia.
Grilli made a quick impression, pitching well in high leverage situations and earned manager Clint Hurdle's trust, prompting him to become the team's setup man next year.
On the same day, the Pirates acquired struggling first baseman Gaby Sánchez from the Miami Marlins for outfielder Gorkys Hernández and a compensatory 1st round pick in the 2013 MLB draft.
Martin, while providing decent offensive numbers, was considered to be a major defensive upgrade over the previous year's platoon of Rod Barajas and Michael McKenry.
On December 26, the Pirates traded established closer Joel Hanrahan and infielder Brock Holt to the Boston Red Sox for reliever Mark Melancon, and prospects Jerry Sands, Ivan Dejesus, and Stolmy Pimentel.
[15] This trade was widely viewed at the time as a negative for the Pirates,[16] and has only looked worse as Cole emerged as one of the best pitchers in baseball.
In the two seasons since the trade, Gerrit Cole accumulated 12.1 Wins Above Replacement, while the players the Pirates received have combined for 2.9 WAR[17] During the season, the Pirates made a major trade with the Tampa Bay Rays, giving up Tyler Glasnow, Austin Meadows, and Shane Baz for veteran pitcher Chris Archer.
Despite making win-now moves like the trade for Archer and Keone Kela the summer before, the Pirates had a quiet offseason in 2019, spending only $7 million on major league free agents.
[21] Despite an underwhelming rotation, the team's offense was powered by a breakout season from Josh Bell and impressive play from Bryan Reynolds, who was acquired by Huntington in the McCutchen trade of 2018.
In addition to their on-field struggles, the team suffered from problems off the field as well, including brawls,[23] fights between players in the clubhouse,[24] and the arrest of closer Felipe Vazquez.