[1] Prior to entering law enforcement, Tompkins was the director of marketing and public affairs at Dimock Community Health Center.

[5] He also received attention as one of several prominent Black officials, along with District Attorney Rachael Rollins and Police Commissioner William G. Gross, in major criminal legal system roles in Boston when their terms overlapped starting in 2019.

According to the suit, Johnson lay dying on the floor of a booking cell for nearly two hours without assistance from any staff while awaiting transportation for court-ordered alcohol use treatment.

[17] In 2021, Tompkins proposed forced treatment of substance use disorders in Suffolk county facilities for unhoused people in Boston, especially those living in the Mass and Cass neighborhood.

[19][20][21] In October 2021 Acting Mayor Kim Janey implemented many elements of this plan through an executive order with actual evictions starting in early November.

[25][26] Though he paid the fine, Tompkins stated his niece was qualified for the role in the External Affairs Office as she was a marketing professional and that the employees assisting with childcare were doing him a favor.