[1] Holmes became a community activist in the mid-1990s after being mentored by Chicago alderman (city councilman) Terry Peterson, who he worked as an aide to.

He has also often acted as a liaison between community members in gun violence-stricken neighborhoods in the Chicago area and the police, as he is regarded as having earned the trust of many residents.

[1] In 2015, Holmes faced personal tragedy with gun violence when his 32-year-old daughter, Tamara Sword, was fatally shot at a gas station in Indianapolis.

[4][7] Holmes worked for Illinois State Representative Milton Patterson, who tasked him with focusing on the needs of senior citizens in his district.

Holmes began working with local police to solve cases involving elder victimization.

[1] In late-2021, Holmes helped the Chicago Police Department apprehend his own brother for committing package theft.

[10] Dolton's elections tend to be more competitive than those in most other municipalities in the Chicago area's "southland" region, often seeing many candidates run.

[12] Holmes ran in a four-person Democratic primary election against incumbent mayor Riley Rogers, fellow village trustee Tiffany Henyard, and Robert Shaw (a politician who was the brother of the deceased past Dolton mayor William Shaw).

[2][15] In September 2021, Holmes was the only village trustee to vote in support of Henyard's request to hire a media consultant at a pay rate of $3,000 per month.

[20] In the same election cycle, Holmes filed a challenge with the Cook County Clerk's Office against former mayor Rogers' nominating papers to run for an additional term on the Thornton Township Trustees of Schools Board.

[25] In April 2024, a lawsuit was filed which alleges that Holmes sexually assaulted a Dolton village employee while on a May 2023 Dolton-related business trip to Las Vegas.