Several days later, on Nov. 22, Hasselgard left New York in June Eckstine's car. By then, June and Hasselgard were romantically involved. June was reportedly heading to Chicago to have her husband sign divorce papers. Billy was appearing in Chicago at the time. Also in the car, according to Billboard in 1948, were Milt Ebbins, Hasselgard's mananger, and Bob Redcross, Billy Eckstine's driver and road manager. Unclear is whether Hasselgard actually planned to fly down to Mexico City from Chicago or whether he and June were going to drive on to Nevada to marry or if he was planning to travel to Los Angeles with Ebbins to sign his Capitol deal. What is known is that in the early morning hours of Nov. 23, June was behind the wheel just outside of Hammond, Ill., Hasselgard was in the passenger seat, and Redcross and Ebbins were in the back sleeping. Why the car wound up more than three hours south of Chicago instead of heading north after reaching Indianapolis is unclear. At some point, the car skidded—either because June hit ice, fell asleep or, as Billboard reported, a trailer truck forced the car onto the shoulder, causing the car to flip over. A combination of the three is possible as well. When the car flipped, Hasselgard and Eckstine were thrown from the vehicle. Hasselgard, 26, was killed instantly and Eckstine suffered a broken arm and lacerations, Redcross broke a toe and Ebbins was apparently unharmed. Whatever action June was supposedly due to take against her husband in Chicago was put off. According to Jet magazine in 1953, Billy rushed to her side at the hospital after the accident. She held off filing for divorce until 1952 and in 1953, she wound up with a $23,750 alimony payment (about $215,000 in today's dollars).