He has previously played in MLB for the San Francisco Giants, New York Yankees, Philadelphia Phillies, and Milwaukee Brewers.

He lived with his mother while his father attended Carson–Newman University in Jefferson City, Tennessee, where Lorenzo played running back on the football team.

Lorenzo gave up his dream of making the National Football League (NFL) to be close to his son and returned to Fort Meade in 1989.

[4] McCutchen was one of the top football recruits in the state of Florida, with his high school position being wide receiver, but opted for a baseball career.

[8] He played again for Altoona, as well as for the Triple-A Indianapolis Indians, and hit a combined .265/.329/.388 with 11 home runs and 21 stolen bases in 513 at bats.

[8] In 2007 he also played for the Phoenix Desert Dogs, he was on the Arizona Fall League All-Prospect Team and named a Rising Star.

[10][11] He played the entire season with Indianapolis, and batted .283/.372 (10th in the IL)/.398 with 12 home runs, 68 walks (3rd in the league), 34 stolen bases (7th), and 145 hits (9th), in 512 at-bats.

[8] On June 3, 2009, after the Pittsburgh Pirates traded starting center fielder Nate McLouth to the Atlanta Braves, McCutchen was called up to MLB for the first time.

[20] McCutchen finished fourth in the voting for the National League Rookie of the Year Award, behind Chris Coghlan, J.

"[24] McCutchen finished the month of May with career-best numbers, hitting .327 with a .901 OPS, which drew comparisons with Tampa Bay Rays All-Star Carl Crawford.

[28] On August 30, 2011, McCutchen hit a ninth-inning homer against the Houston Astros to become the eighth Pirates player to record at least 20 home runs and 20 stolen bases in one season.

[20] McCutchen finished third in the NL Most Valuable Player Award voting, behind San Francisco's Buster Posey and Milwaukee's Ryan Braun.

[20] His efforts helped lead Pittsburgh to a winning record and the postseason for the first time since the 1992 Pirates team, led by Barry Bonds.

McCutchen won the National League MVP over Arizona's Paul Goldschmidt and St. Louis' Yadier Molina, becoming the first Pirate to win the award since Bonds in 1992.

[20] On April 26, 2016, for the second time in his career, McCutchen hit three home runs in a single game against the Colorado Rockies, ending a 3-for-23 slump.

[20] During the 2016 Winter Meetings, Pirates' general manager Neal Huntington reportedly came close to trading McCutchen to the Washington Nationals.

[72] As of 2018, McCutchen was 2nd of all Pirates players in career power-speed number (185.6; behind Barry Bonds), 4th in home runs (203; behind Hall of Famers Willie Stargell, Ralph Kiner, and Roberto Clemente), 7th in walks (685), extra base hits (539), and sacrifice flies (47), 9th in doubles (292) and intentional walks (63), and 10th in total bases (2,452) and hit by pitch (61).

[73][74] On January 15, 2018, the Pirates traded McCutchen to the San Francisco Giants, along with cash considerations, in exchange for Kyle Crick, Bryan Reynolds, and $500,000 of international bonus slot money.

[76] On May 11, the Giants traveled to PNC Park in Pittsburgh, and McCutchen received a standing ovation from Pirates fans.

On August 31, 2018, the Giants traded McCutchen to the New York Yankees in exchange for infielder Abiatal Avelino and pitcher Juan De Paula.

[87] McCutchen made his Brewers debut on April 7, and recorded a double to the right field corner off Chicago Cubs starter Kyle Hendricks in his first at-bat.

[89] On September 23, McCutchen notched his 1,000th career RBI, scoring Rowdy Tellez on a fielder's choice off of Cincinnati Reds starter Luis Cessa.

[93] He made his return to PNC Park at the Pirates' home opener on April 7, 2023, where he received a standing ovation that lasted over a minute prior to his first at bat.

[95] On September 6, the Pirates placed McCutchen on the 10–day injured list after suffering a season–ending partial left Achilles tendon tear.

[98] On April 14, 2024, McCutchen hit his 300th home run, a two-run shot off of Philadelphia Phillies reliever Ricardo Pinto.

[38] On March 25, 2015, McCutchen cut his dreadlocks, which were sold through MLB's website via auction, with all proceeds benefiting Pirates Charities.

McCutchen appeared as Uncle Larry during a May 2020 episode of MLB Network's Intentional Talk, sporting sunglasses, a wig, and a half-unbuttoned jersey.

[105][106] The Uncle Larry gig spawned a rash of merchandise, including t-shirts, a bobblehead, and a trading card in 2021 Topps Allen & Ginter.

[107] McCutchen proposed to his longtime girlfriend Maria Hanslovan on the December 11, 2013, episode of The Ellen DeGeneres Show.

[112] In May 2021, McCutchen provided voice acting for an episode of the Disney Junior television show Puppy Dog Pals.