In 2008, Hawkins joined theCleveland Indians baseball team as an advance scouting intern.[2] He took a full-time role as a scout for the organization in 2009.
Hawkins was reported to be the scout that found perennial all star Jose Ramirez. On 7/1/2025, while being interviewed on 670am out of Chicago, Hawkins said that he did not discover Ramirez. Hawkins was named the team's assistant director of player development in 2010 and the director of player development in 2015.[3] He was named the Indians' assistant general manager in 2016. He was named Sports Illustrated top young up and coming baseball executive in 2015.[2]
On October 15, 2021, theChicago Cubs hired Hawkins as their general manager.[4][5]