On 14 April 1942, he took command of Torpedo Squadron Three (VT-3) aboard , then based at Kaneohe Naval Air Station. On 27 May 1942, VT-3 was transferred to following the Battle of the Coral Sea, replacing that ship's own Torpedo Squadron 5 (VT-5). "Yorktown" sailed with VT-3 for Midway Island and entered battle on 4 June 1942. During this crucial encounter, Massey was killed while leading his squadron in a low-level attack against the Japanese aircraft carrier Hiryū. He was last seen Escorted by only six F4F Wildcat fighters, led by Lieutenant Commander John Thach, ten out of VT-3's twelve TBD's were lost. For his heroism in pursuing the attack on "Hiryu", Massey was posthumously awarded the Navy Cross.