Jenkins formally entered county politics in 2007 when he succeeded
Andrea Stewart-Cousins on the
Westchester County Board of Legislators, representing the 16th district which includes much of western Yonkers. He had previously run unsuccessfully for Yonkers City Council president in 1997. Jenkins was elected as Chairman of the Board of Legislators in 2010 and served in the post until 2013. In 2016, Jenkins announced he would challenge incumbent Westchester County Executive
Rob Astorino in the next year's election. He had previously attempted to win the Democratic nomination for county executive in 2013, but failed to garner enough support at the party convention and lost the
nomination to New Rochelle Mayor
Noam Bramson. Jenkins and Astorino had clashed multiple times during the former's tenure as Board of Legislators chairman in lawsuits including ones challenging Astorino's capital projects, county transportation and his authority to oversee the management of
Playland Amusement Park. However, Jenkins lost his primary bid for county executive to then-State Senator Latimer, who also went on to unseat Astorino. However, after taking office Latimer appointed Jenkins as deputy county executive. While serving as deputy county executive, Jenkins also held a number of other positions including Chair of the New York State Independent Redistricting Commission and Treasurer of the New York State Democratic Committee. Latimer resigned as Westchester County Executive on January 2, 2025 after being
elected to Congress to represent New York's 16th congressional seat. Latimer was briefly succeeded by County Emergency Services Commissioner Richard G. Wishnie, but county legislators unanimously voted for Jenkins to serve as executive until a special election could be held on February 11, 2025. Jenkins had previously announced he would run in that special election after Latimer won his congressional race. Jenkins won a February 12, 2025 special election for county executive, beating Republican Party candidate Christine Sculti with over 60 percent of the vote. Later that November, Jenkins won his first full term as County Executive in the general election. ==Electoral results==