Gentry attended the University of Arkansas – Fort Smith during his freshman and sophomore years.
He then attended the University of Arkansas, where he played college baseball for the Arkansas Razorbacks baseball team.
The Texas Rangers selected him in the 10th round (298th overall) of the 2006 MLB draft.

The Rangers promoted Gentry to the majors on September 1, 2009, but he did not see significant playing time.
He began the 2010 season with the AAA Oklahoma City RedHawks, but was called up to the majors on April 27 due to Nelson Cruz being placed on the 15-day disabled list.
On May 15, he was optioned back to Oklahoma City.

In 2011, Gentry batted .271 in 133 at-bats, with 18 steals in 18 attempts.
He hit his first MLB triple on September 11 against the Oakland Athletics.
A few days later, on September 23, he hit his first Major League home run, an inside-the-park home run against the Seattle Mariners.
At the end of the season, he was named the Rangers' Rookie of the Year.

In 2012, Gentry batted .304, a career high.
He also hit his first outside-the-park home run, a two-run homer to left in Toronto on April 30.
Gentry pitched the final inning of a 12–1 loss at the hands of the Oakland Athletics on June 4.
He allowed two runs on three hits and a walk.

In 2013, Gentry hit two home runs, stole 24 bases and had an on-base percentage of .373, all career highs.
He broke his left hand in June against the Oakland Athletics on a bunt attempt.
Gentry was named Rangers' player of the month in September after batting .354 with 10 stolen bases, 10 runs, 2 doubles, a triple and four RBI.
He also won the Rangers' Wilson Defensive Player of the Year Award.
In 102 games, he committed 2 errors, had 7 outfield assists, saved 12 runs and had the best UZR on the team.
Gentry attended the University of Arkansas – Fort Smith during his freshman and sophomore years. He then attended the University of Arkansas, where he played college baseball for the Arkansas Razorbacks baseball team. The Texas Rangers selected him in the 10th round (298th overall) of the 2006 MLB draft.
The Rangers promoted Gentry to the majors on September 1, 2009, but he did not see significant playing time. He began the 2010 season with the AAA Oklahoma City RedHawks, but was called up to the majors on April 27 due to Nelson Cruz being placed on the 15-day disabled list. On May 15, he was optioned back to Oklahoma City.
In 2011, Gentry batted .271 in 133 at-bats, with 18 steals in 18 attempts. He hit his first MLB triple on September 11 against the Oakland Athletics. A few days later, on September 23, he hit his first Major League home run, an inside-the-park home run against the Seattle Mariners. At the end of the season, he was named the Rangers' Rookie of the Year.
In 2012, Gentry batted .304, a career high. He also hit his first outside-the-park home run, a two-run homer to left in Toronto on April 30. Gentry pitched the final inning of a 12–1 loss at the hands of the Oakland Athletics on June 4. He allowed two runs on three hits and a walk.
In 2013, Gentry hit two home runs, stole 24 bases and had an on-base percentage of .373, all career highs. He broke his left hand in June against the Oakland Athletics on a bunt attempt. Gentry was named Rangers' player of the month in September after batting .354 with 10 stolen bases, 10 runs, 2 doubles, a triple and four RBI. He also won the Rangers' Wilson Defensive Player of the Year Award. In 102 games, he committed 2 errors, had 7 outfield assists, saved 12 runs and had the best UZR on the team.
Craig Gentry