He is also an actor who co-starred on the television series Brad Meltzer's Decoded that was aired on the History Channel with 23 episodes spanning two seasons.

Rolle was mobilized and deployed to Afghanistan from October 2018 through April 2019 serving as the USFOR-A Chief Investigator for Gross Violations of Human Rights (Leahy Law).

[1] Rolle has served as an adjunct professor of Criminal Law at Mount Saint Mary's University and Frederick Community College.

The firm handled Criminal Defense cases, personal injury/auto accidents, domestic relations, business law, and wills and estates.

[citation needed] Rolle also won full acquittals on three courts-martial he handled while on active duty in the US Army, and also on five recent civilian trials including a felony drug case, first-degree assault, and domestic violence.

[6] It is the first time ever that a "sitting" judge appointed by Governor Martin O'Malley (Danny O'Connor in 2014) lost the general election.

[9] He has been awarded the Governor’s Citation for his work in the area of forfeiture of drug dealer assets and as chief narcotics prosecutor.

[1] Rolle joined the United States Army Reserve in September 2001, receiving a direct commission in the Judge Advocate General's Corps.

In January 2008, he was called to active duty and mobilized for a thirteen-month tour[11] at Fort Meade, Maryland, and was responsible for most cases arising from the Walter Reed Army Medical Center in Washington, DC.

Rolle was again called to active duty in late 2009 early 2010 to act as Operations Officer for the H1N1 Regional Joint Task Force Alpha.

During his active duty tours, Rolle tried 3 full panel courts-martial, representing soldiers charged with numerous offenses.

From October 2018 to May 2019, LTC Rolle was mobilized and deployed to Afghanistan as the Chief Investigator for Human Rights Violations in support of the NATO mission.

In July 2010, he joined the cast of Brad Meltzer's Decoded, which premiered December 2, 2010, on the History Channel as an investigator and legal expert who looks into alleged conspiracies and unsolved mysteries around the world.