On his birthday he went to the racetrack and was astounded to see that in the fifth race (scheduled for five o'clock) a horse called Pentagram was running, with the odds of 55 to 1.
Rushing off to the bank, the man was astonished to find he had $5,555.55 in his bank account.
He withdrew the whole amount, dashed back to the races and bet all of it on Pentagram to win.
Pentagram, obviously,
Spoiler: