Born in
San Diego, California, Gentry started playing basketball at DeQuincy Highschool, in DeQuincy Louisiana earning a scholarship at
McNeese State University. He competed in the
NCAA Division I, with the
Cowboys under coach
Tic Price in his
last year as senior, averaging 10.8 points per game, as the
Cowboys lost in the Midwest Regional to the
Bulldogs. Undrafted, Gentry moved to Europe, starting his professional career in the
Portuguese League, playing one season on the Azorean team,
Lusitânia, before he moved to
Ginásio da Figueira. There, he improved his scoring ability, increasing from 13.5 points per game in 2004–05, to 16 points per game in the next season. He returned to Angola, to play another season at Petro de Luanda, but with much less success than before, he moved to
Interclube on 16 September 2009. The 33-year-old returned to Portugal on 25 August 2010, signing with
CAB Madeira, and helping them win the Portuguese Cup, while averaging 16.7 points per game in the regular season, and 15.3 on the playoffs. and became an important player for them in the following five years, winning four league titles and fourteen other cups. and left the club in 2016 to play for a second time for CAB Madeira. He is now coach at Lobos da Malveira ==Honours==