Considered a top prospect for the 2016 Major League Baseball draft,[8][9] the Cincinnati Reds selected Trammell with the 35th overall pick.[10] He signed with the Reds and was assigned to the Billings Mustangs of the Rookie-level Pioneer League, posting a .303 batting average with two home runs, 34 RBIs, six triples and 24 stolen bases in 61 games.[11] In 2017, he played for the Dayton Dragons of the Single–A Midwest League, where he slashed .281/.368/.450 along with 13 home runs, 77 RBIs and 41 stolen bases in 129 games,[11] and in 2018 he played for the Daytona Tortugas of the High–A Florida State League, batting .277 with eight home runs, 41 RBIs and 25 stolen bases in 110 games.[11] He represented the Reds in the All-Star Futures Game and was named the MVP of the game after hitting a go-ahead home run along with a triple.[12] The Reds invited Trammell to spring training in 2019 as a non-roster player[13] and he began 2019 with the Chattanooga Lookouts of the Double–A Southern League,[14] and again appeared in the All-Star Futures Game.[15]
On July 30, 2019, the Reds traded Trammell to the San Diego Padres in a three-team trade, where the Reds acquired Trevor Bauer and the Indians acquired Yasiel Puig, Scott Moss, Franmil Reyes, Logan Allen, and Victor Nova.[16] The Padres assigned Trammell to the Amarillo Sod Poodles of the Double–A Texas League[17] where he hit .229 in 32 games with four homers and 32 RBI.[11]
On August 30, 2020, the Padres traded Trammell, Ty France, Andrés Muñoz, and Luis Torrens to the Seattle Mariners in exchange for Austin Nola, Dan Altavilla, and Austin Adams.[18] On November 20, Trammell was added to the 40-man roster.[19]
Trammell made his MLB debut for the Mariners on April 1, 2021, playing center field against the San Francisco Giants. In his debut he was walked twice, including drawing a bases loaded walk in the bottom of the eighth inning for his first major league RBI.[20] Trammell collected his first hit on April 3, an RBI double (off Logan Webb) that scored Evan White, in the bottom of the fourth inning.[21] He hit his first MLB home run off Michael Pineda of the Minnesota Twins on April 10[22] and appeared in 51 games for Seattle in his rookie campaign, slashing .160/.256/.359 with eight home runs and 18 RBI.[23] In 2022, he played in 43 games for the big league club, but again struggled to a .196/.284/.402 slash with four home runs and 10 RBI.[23]
Before the 2023 season, Trammell underwent surgery to repair a broken hamate bone in his right hand that he suffered after being struck in the hand in a late offseason workout.[24] He was activated off the injured list on April 30[25] and in his return, hit a grand slam off Chris Bassitt of the Toronto Blue Jays.[26] In 22 games for Seattle, he batted .130/.286/.326 with three home runs and 11 RBI.[23] On March 28, 2024, Trammell was designated for assignment after failing to make Seattle's Opening Day roster.[27]
On April 2, 2024, Trammell was claimed off waivers by the Los Angeles Dodgers.[28] He had six at-bats in five games for the Dodgers with three strikeouts[23] and was designated for assignment on April 16.[29]
On April 18, 2024, Trammell was claimed off waivers by the New York Yankees.[30] In five games for the Yankees, he was used primarily as a defensive replacement, and singled in his only at–bat. Trammell was designated for assignment by New York on May 4.[31] He cleared waivers and was sent outright to the Triple–A Scranton/Wilkes-Barre RailRiders on May 7.[32] As he appeared for both the Yankees and Dodgers in the 2024 season, he was guaranteed a World Series ring from the 2024 World Series regardless of who won.[33] After the season ended, the Yankees re-added Trammell to their 40-man roster.[34]
On November 4, 2024, the Yankees traded Trammell to the Houston Astros in exchange for cash considerations.[35] He made 52 appearances for the Astros in 2025, batting .197/.296/.333 with three home runs, 12 RBI, and three stolen bases. On December 5, 2025, Trammell was removed from the 40-man roster and sent outright to the Triple-A Sugar Land Space Cowboys.[36]
Trammell began the 2026 season with Triple-A Sugar Land. On April 10, 2026, the Astros selected Trammell's contract, adding him to their active roster.[37]