Cliff Whitlow

Cliff Whitlow was a mature man who played a game of high-stakes poker with a “he-witch,” and won.

History
On Bobby's tip, Sam and Dean had begun investigating the case of a 25 year-old man who apparently died of old age, and broadened their investigation to include missing persons cases. They met with Mrs. Whitlow whose husband, Cliff, had been missing since the previous Tuesday. She showed him the most recent photo of Cliff holding a golf trophy and sporting a USMC tattoo on his right arm. She told them her husband always worked a bit late on Tuesdays and always came straight home afterward, so she immediately knew something was wrong when he didn’t return. Dean excused himself and ducked into their office to look for clues. He rifled through the pockets of a suit jacket draped over the desk chair and discovered a receipt from Madame Liu's Golden Palace, then knowingly muttered, “Workin’ late, my ass.”

The boys went to Madame Liu’s and learned that Cliff had booked the same room every Tuesday, at an hourly rate. They approached the room and started to pick the lock, expecting to find a gooey corpse. Suddenly they heard a man begin shouting from inside. They broke the door open and found a man in bed with two women. They apologized and started to leave until Sam noticed a USMC tattoo on his forearm exactly like the one in Cliff Whitlow’s photo. When asked, the man denied ever having heard of Cliff Whitlow. Then Sam seized Cliff’s wallet from beside the bed, and Dean literally uncovered his identifying birthmark, per Mrs. Whitlow’s information. Cliff got robed and paid and dismissed his company. He then begged the boys please, for the love of God, not to tell his wife, as he wanted her to go on believing he was dead.

They asked him exactly how it was that he was so young again; he replied that he couldn’t tell them, to which Dean replied they would indeed tell his wife if he didn’t. Sufficiently afraid of that, he revealed that he was approached by a guy named Patrick at a bar who invited him to play a game of poker. Patrick gave him 25 “weirdo” poker chips, chanted some "mumbo humbo" over the them, and declared that they were years. Cliff said he thought the guy was crazy but agreed to play anyway, and won. Sam asked what he chanted, Cliff responded that he didn’t know, and he didn't seem to care, because his dodgy hip was all better, he no longer needed glasses, and he was getting extra services from Madame Liu’s, at no extra charge. He reckoned the man was a miracle worker.

When Dean asked where they might find Patrick, Cliff replied “He finds you,” and added that he’d told him he never stayed in one place too long, because liked to keep moving. Dean’s parting shot to Cliff: "stay classy."

When Patrick's companion, Lia, later presented Bobby and Dean with a reversal spell, she stated that casting it would put all surviving poker players back to normal. It was not mentioned whether or not Cliff returned home to his wife.

Appearances

 * Season 5
 * The Curious Case of Dean Winchester