Andrew McCutchen Reveals Most Important Moment with Pirates
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PITTSBURGH —Andrew McCutchen has had one of the better careers in Pittsburgh Pirates' history and many incredible moments.
McCutchen was a five-time All-Star (2011-15), four-time Silver Slugger Award winner (2012-15), 2012 Gold Glove Award winner and 2013 National League MVP in his first stint with the Pirates, marking one of the best tenures for the historic franchise.
The Pirates great is currently with MLB Network as a guest host, helping them out with their postseason coverage, and studio host Greg Amsinger named his nine favorite moments of McCutchen's career.
McCutchen looked through the list, but noted that him winning the Roberto Clemente in 2015 was his favorite memory.
Roberto Clemente Award's Importance to Clemente
The Roberto Clemente Award recognizes the player who "best represents the game of Baseball through extraordinary character, community involvement, philanthropy and positive contributions, both on and off the field."
It was originally the Commissioner's Award, but MLB renamed it to the Roberto Clemente Award in 1973, following the Pirates' Hall of Famer's death in 1972.
Clemente was bringing humanitarian aid to earthquake-stricken Nicaragua on Dec. 31, 1972, when his plane, carrying too much cargo, crashed into the ocean off the coast of Isla Verde, Puerto Rico, near his hometown of Carolina.
Every team nominates a player for the award, but only two Pirates players have won it, Clemente's teammate and fellow Hall of Famer Willie Stargell in 1974 and Clemente in 2015.
"Winning that award for me in 2015 that was more important than the MVP, the All-Stars, all of it. Just because of what it represents, understanding I was doing that in a Pirates uniform, representing Roberto Clemente himself and his family. It was a special moment for me, special moment for his family as well."
With @TheCUTCH22 in Studio 42, Greg HAD to rank his top career moments! ⬇️ pic.twitter.com/ryIWUfqC5R
— MLB Network (@MLBNetwork) October 5, 2026
Other Great Moments in McCutchen's Career With Pirates
McCutchen had an incredible career with the Pirates, spanning two tenures, 2009-17 and then 2023-25.
His rookie season in 2009 was impressive, with a three-home run game against the New York Mets at PNC Park on Aug. 1 and then a walk-off home run against the reigning World Series Champions Philadelphia Phillies on Aug. 25.
The moment most Pirates fans remember is McCutchen's two-run walk-off home run against the St. Louis Cardinals at PNC Park on July 11, 2015.
Pittsburgh trailed St. Louis 5-4 in the 14th inning, before McCutchen gave them a big 6-5 win, in a series they won three out of four against their divisional foe, closing the gap to 2.5 games at the All-Star break.
He also participated in the 2012 Home Run Derby and hit a home run in the 2015 All-Star game.
McCutchen's peak came with the best period for the Pirates in the 21st century, as they ended their record 20 consecutive losing seasons from 1993-2012, and made the playoffs three straight times, 2013-15.
One of the best moments of his second tenure was passing Clemente on the Pirates' all-time home runs list to move into third place in 2025, ending with 248.
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Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.