Perhaps Ruby's most notorious hard-luck bout at Indy came in 1969. With race leader Mario Andretti experiencing overheating problems, Ruby was in a strong position to score a victory. During a pit stop around the halfway point, a crew member motioned Ruby to pull away too soon. The refueling nozzle was still engaged in the car's left saddle tank, and as Ruby dropped the clutch, the car lurched forward. The nozzle ruptured a hole in the gas tank, ending Ruby's day.