Gentry was born and raised in Memphis, TN where he attended Power Center Academy (PCA) High School. Growing up in a tough part of town, Gentry credits rugby for saving his life and putting him on a different path than many of his friends.
As part of Memphis Inner City Rugby (MICR), Gentry played 8-man and was named captain and two-time MVP at PCA Rugby Club. He proved himself on the pitch and was selected to compete with the Tennessee All-Star Tri-Stars 15s team in 2013-2016, including in Las Vegas in 2015.
While with the Tri-Stars, his coach encouraged him to try out for the USA Rugby South U19 side. Gentry went on to represent the US in 2014-2016 and was named MVP of the squad. In 2016, he was named to the Junior All-American team competing for the USA U19 select side. Next, Gentry returned to Las Vegas when he was selected for the 7s Atavus side, a club based in Seattle, WA.
Before heading off to college at Arkansas State University, Gentry had another opportunity to be an ambassador for MICR. Calvin starred, alongside MICR founder Shane Young, in The Rugby Boys of Memphis, an award winning film in the Tribeca Film Festival. The film touches on the immense impact rugby had on Calvin’s life and can be found on Amazon Prime.
At Arkansas State Gentry proved himself playing 8-man, center, and wing and was named to the Collegiate All-American team. Before earning his Associates in 2019, Gentry played with Tiger Rugby 7s in Dallas in 2018. He then transferred to University of Memphis to continue his career and education and was once again named to the Collegiate All-American team in 2019.
Gentry currently competes with the Memphis Tigers Rugby Club, a collegiate club, in which he was named MVP two years ago. In 2019, Calvin travelled to London on an invite from the Harlequins Rugby Foundation to train for a day with the squad and speak at a charity event.
In October 2021, Gentry took part in the Inaugural Premier Rugby Sevens (PR7s), first ever professional 7s tournament in the US, with the Headliners.