A standout at Cy-Fair High School near Houston, Grossman was the sixth-round draft pick of the Pittsburgh Pirates in 2008. The Astros acquired Grossman at the 2012 trade deadline in the deal that sent Wandy Rodriguez to Pittsburgh. Grossman hit .240 with 11 home runs and 63 RBIs in parts of three seasons with the Astros. Early struggles in 2015 led to a demotion to AAA and Grossman was released after the season.

Undeterred, the switch-hitter has continued his big league career with the Twins and Athletics. Through 2019, he has hit .253 with 42 homers and 231 RBIs over seven seasons.