That same year, May joined the election campaign of Muriel Bowser, a Fenty protégé who was running for a seat on the District Council from Ward 4. May had first met Bowser in 2010, when they both worked on Fenty's unsuccessful campaign to win renomination as the D.C. Democratic Party's candidate for mayor. May and Bowser's relationship continued over the next three years. In January 2013, May spotted Bowser at an awards ceremony in the Congress Heights neighborhood, and offered her support. When Vision of Victory opened Roundtree Residences, a 91-unit affordable-housing community, May invited Bowser to attend to give the mayoral candidate more visibility in Ward 8. May quickly became part of a very tight inner circle of Bowser supporters. Bowser named May her Ward 8 field coordinator when Bowser ran for the Democratic Party's mayoral nomination in 2013. According to The Washington Post, May pledged to help Bowser win the Ward 8 Democratic Party straw poll. Bowser upset then-incumbent D.C. Mayor Vincent C. Gray. Gray's loss in the straw poll was a turning point in the Democratic nomination, Bowser defeated Gray in the Democratic primary on April 1, 2014, then easily won the mayoralty in the general election in November 2014.
