He entered politics early out of law school in 2000, when then-state representative Dorothy Bendross-Mindingall hired him as a legislative aide. He then worked as deputy of policy for former US attorney general Janet Reno's gubernatorial campaign. A couple years later, after working first as a prosecutor and then in private practice, he vied for the mayoralty of the newly incorporated City of Miami Gardens in 2003 where he lost. He was appointed to the Miami Gardens council in 2008 and 4 years later was elected mayor, the second African-American to hold the position. Miami Gardens is Florida's largest city with a majority African American population and the 3rd largest city in Miami-Dade County.
When running for Miami-Dade County Commission he faced Sybrina Fulton, the mother of Trayvon Martin, who was killed by George Zimmerman in 2013. There were notable as people like Hillary Clinton, Cory Booker, Elizabeth Warren and other high ranking figures in the Democratic Party who endorsed Fulton. However, Gilbert won a close race in August winning 50.5%, as such a runoff was not needed.
Following the retirement of incumbent Rep. Frederica Wilson, Gilbert announced his candidacy for the United States Congress in June 2026. He was endorsed for the seat by Wilson, Mayor Daniella Levine Cava, and Mayor Eileen Higgins. In the primary election for the Democratic nomination, Gilbert faced progressive state Sen. Shevrin Jones, Kendrick Meek Jr.—son of Kendrick Meek—and four others. During the campaign, Gilbert received criticism from the local press for attacking Jones for voting in-favor of renaming Palm Beach International Airport to "President Donald J. Trump International Airport" after Gilbert approved of renaming a street after Donald Trump in 2024. In August 2026, mass text messages were sent to residents of the district claiming Jones was HIV-positive; the text were sent from a group impersonating Equality Florida in "violation of federal law." An Equality Florida spokesperson criticized Gilbert and other candidates for their "unwillingness to denounce this smear tactic." Gilbert later released a statement, saying: "It's a lie. It's evil, hurtful, and it needs to stop." On August 18, 2026, Gilbert narrowly won the Democratic nomination, receiving 34.4% of the vote to Jones' 32%. In the general election, Gilbert is facing Republican nominee Mayonna Te Brown; however, winning the Democratic primary in the 24th district is considered "tantamount to election."
Personal life
Gilbert is known for his love of bowties and frequently wears them. He is a brother in Omega Psi Phi fraternity.
