wouldn't you know who won the pony

refers to the story told by Jim Cornette when a local wrestling promoter , faced with declining attendance , rigged a lottery to give a way a pony so his son won it , so we did not lose money on the deal . As a result anything is is obviously rigged is referred to as wouldn't you know who won the pony .

Implies that the previously stated is rigged; local wrestling promoter, as told by Jim Cornette, gave away a pony to increase ticket sales and, to avoid losing money, rigged the raffle to ensure his son would win the pony