Two years later, he recurred during the first season of the comedy television series Sirens,[1] after which he was promoted to a series regular during its second season.[12] Segarra then began a recurring role on the NBC police procedural drama Chicago P.D.[13] He also appeared in the 2015 comedy film Trainwreck.[14] Segarra originated the role of Emilio Estefan in the musical On Your Feet!, which opened at the Marquis Theater on Broadway on November 5, 2015.[15] His final performance took place on July 10, 2016.[16][17] Following his final appearance on Chicago P.D. in May 2016, Segarra was cast as a series regular on the CW superhero television series Arrow for its fifth season.[18] He portrayed the series' adaptation of the comic book character Adrian Chase.[9] He then returned in a guest starring capacity during the series' sixth and eighth seasons.[19]