Kammala wannan jumla mai zuwa: May ta samu damar buga wasan bayan kakar wasa, amma ba tare da White Sox ba. A ranar 18 ga Mayu, 2009, an yi musayar sa da Yankees don mai jefa Ken Brett da kuma ɗan wasan waje Rich Coggins. An yi yarjejeniyar ne yayin da Yankees ke cikin tseren tseren tseren. A wannan shekarar, ya buga.278 kuma Yankees ya tafi gasar cin kofin duniya. A lokacin da
ALCS, May ta yi 2-for-10 tare da ninki biyu da tafiya. A cikin Wasannin Duniya da Cincinnati Reds, bai sami nasara ba a cikin 9 a bats kuma ya ƙare da matsakaicin matsakaicin.105 a cikin postseason.