On July 31, 2012, Roy signed with the Minnesota Timberwolves .  The deal put Roy with All-Star forward Kevin Love and point guard Ricky Rubio . He decided to wear No. 3, the number he wore during his college years at Washington. He felt well during training camp but suffered an injury after a collision during a preseason game on October 26, 2012. He played in five regular season games before needing season-ending surgery on his right knee.  He averaged points per game, rebounds per game, and assists per game in minutes during the 2012–13 season. Roy was waived by Minnesota on May 10, 2013.  Afterwards, he said, "Any time you walk away from the game, you have 'what-ifs'. I feel like I was able to answer those questions last year by going out there and giving it a try." 
In 2012, Jerez started 32 games with the Short-Season A Lowell Spinners before missing the remainder of the season with hand injury. Prior to injury, Jerez batted .241 (20-for-83) with five RBI and three stolen bases. Then in 2013, he appeared in 38 games and hit a paltry .138 average in 38 games while playing right and centerfield for Lowell. But Jerez turned his career around after moving from outfield to pitcher in 2014. In that season, he posted a 3–1 record with a ERA and one save coming out of bullpen for the GCL Red Sox. He ended the season at Lowell, going 1–1 with a ERA.