In 2009, Drew ran against incumbent mayor
Sebastian Giuliano and lost 52–47%. He ran again in 2011, defeating Giuliano 53-46%. Facing no major party opponent, Drew was re-elected in 2013 with over 80 percent of the vote. In 2015, he was elected to a four-year term as Middletown voters approved an increase in the mayor's term. In 2016, Drew made news when he donated a kidney to one of his constituents. In 2018 Drew gave a TED talk at Wesleyan University on the misconceptions surrounding kidney donation. On January 12, 2017, Drew announced he was forming an
exploratory committee to run for
Governor of Connecticut. in the 2018 election. He withdrew from the race on January 12, 2018, exactly one year after forming an exploratory committee to run, stating that, "Ultimately it became very difficult to raise the required funds to qualify for public financing." == Electoral history ==