On March 29, 2011, McKenry was traded to the Boston Red Sox for minor league RHP Daniel Turpen. On June 13, 2011, he was traded to the Pittsburgh Pirates for cash or a player to be named later.
Pittsburgh Pirates
On June 13, 2011, he was traded to the Pittsburgh Pirates for cash or a player to be named later. McKenry made his debut for the Pirates on June 13 and recorded his first major league hit, a single off of Houston Astros starter J. A. Happ, two days later. He hit his first major league home run on July 8, 2011 against the Chicago Cubs. On July 26, McKenry was involved in a controversial play against the Atlanta Braves in the bottom of the 19th inning. With runners on the corners, Scott Proctor hit a ground ball to Pedro Alvarez, who threw to McKenry, who appeared to tag Julio Lugo out at home. However, home plate umpireJerry Meals called him safe, allowing Lugo to score the walk-off run. McKenry has been given the nickname "Fort McKenry" or simply "The Fort" by fans and media in Pittsburgh due to his defensive skills behind the plate as the Pirates' catcher and the similarity of his name to Fort McHenry, the famous fort in Baltimore known for its role in the War of 1812. On April 14, 2013 McKenry posted his first multi-homer game in the major leagues as he hit 2 home runs, rallying the Pirates to a 10-7 win over the Cincinnati Reds. On July 30, 2013, McKenry underwent knee surgery to repair a torn meniscus and was ruled out for the rest of the 2013 season. On December 2, 2013, the Pirates acquired Chris Stewart from the New York Yankees, and designated McKenry for assignment. He was non-tendered by the Pirates later that day, becoming a free agent.
Second stint with Rockies
McKenry signed a minor league deal with the Colorado Rockies on January 16, 2014.
McKenry signed a minor league deal with the Texas Rangers in December 2015. He was released on May 25, 2016.
St. Louis Cardinals
On May 27, 2016, McKenry signed a minor league contract with the St. Louis Cardinals. The Cardinals called him up on July 7; he made two plate appearances, and was designated for assignment on July 19.
Atlanta Braves
On July 22, McKenry signed a minor league contract with the Atlanta Braves.
On December 16, 2016, McKenry signed a minor league contract with the Tampa Bay Rays. He elected free agency on November 6, 2017.
Retirement
On February 2, 2018, McKenry announced his retirement to join MTSU as the director of player development. On February 9, 2018, the Pittsburgh Pirates announced that he would serve as a studio analyst on the team's pregame and postgame shows.
Personal life
McKenry is the son of Cliff and Shelia McKenry. He married his wife, Jaclyn, in 2008, the same year Jaclyn's father died.