Hook'd on Humor

Poker night with Leyland and the boys

An insider's look at Jim Leyland's poker game with a few close friends.

By HookSlide Sep 26, 2013, 1:06pm EDT

In a forgotten nook of the clubhouse, an old and spacious supply closet has been cleared out and equipped with a card table and some folding chairs. It is several hours after the most recent game, and a group of men sits around this banged up table, enveloped in a dense, blue cloud of cigarette smoke so thick it couldn't possibly have been produced by one individual - but it has.

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Jim Leyland, Dave Dombrowski, Tom Brookens, Mike Ilitch, and Don Kelly look at the cards in their hands, fiddle nervously with their poker chips, and await the outcome of this hand. Leyland mumbles, "This one's for all the marbles, boys, I'll take three," and pushes three cards face down across the table towards Brookens. Although none of the men will say so out loud, they all suspect that Brookens' unorthodox, herky-jerky style of shuffling the cards (a move they have come to label "the windmill shuffle") is a con, and has allowed him to stack the deck in his favor. This is not true. In fact, Brookens' eccentric method of card-shuffling simply stems from the fact that he gets overly excited, and can't control the flailing. More cards usually end up on the floor than in the deck.

The game is five-card draw poker. It is a game that Leyland knows well. Don Kelly is here because his quiet demeanor and relaxed attitude give Leyland comfort, and in this game of high risks and anxiety-ridden reliance on the luck of the draw, Leyland needs what Donnie Baseball's presence provides. Dave Dombrowski is here because he once lost a large amount of money (and a player to be named later) when his King-high flush was outdrawn by Leyland's incredibly lucky four-of-a-kind, runner-runner-runner hand, and Dombrowski is intent on winning his money back. It has been six years, and so far he has been unable to make good on that personal promise. It's not that Leyland is especially good. In fact, Dombrowski has a far superior grasp on the game's strategy, theory, and mathematical formulas. But Leyland has uncanny, gut-level instincts, and even though most of his plays leave Dombrowski scratching his head, when he wins (which he does just 51% of the time), he wins big.

As for the other two players at the table, Mike Ilitch is here only because it is Dombrowski's turn to watch him (the last time they left Ilitch on his own, he showed up the next day with the pelt of a Chinese ferret-badger surgically attached to his scalp), and though he understands very little of how to play the game (or even what century it is), what he lacks in skill he makes up for by buying more than his fair share of pots. The others suspect they could beat him in an actual show of cards, but no one wants to take the risk, especially when he throws $500 million in the pot and then raises the stakes even further by throwing Prince Fielder's contract on the table. As for Tom Brookens, they let him play because he's easy money, a fish, a true sucker.

Leyland gets his three draw cards from Brookens, and frowns at the results. His hand has only improved to a pair of fours, with a King-high kicker. He only stands to lose more money by not folding outright here, but he looks across the table at Don, remembers that one time it paid off to pinch-hit Kelly (The Wizard came through with a late-innings go-ahead home run), and resolves to get involved further in this pot.

Dombrowski taps the table, his cards held tightly against his vest (yes, he is wearing an actual vest, as he always does for these games), and shoots a winning smile at no one in particular. "I stand pat," he says in his most confident voice. He knows he has a losing hand, with his pair of threes and an Ace-high kicker. In fact, he knows that his hand only wins in these situations, with this many unknown opposing hands at the table, 36 percent of the time. But he is a man well-versed in the art of deception, a man entirely familiar with getting something for nothing. His confidence strikes a note of fear in the hearts of the others, with the exception of Don Kelly, whose unwavering embrace of integrity and honesty allows him to detect a falsehood in an instant, the very moment it is uttered. He alone knows that Dombrowski is not holding a "pat hand," but he also understands that Dave is just here to have some fun tonight, and he does not want to interfere.

Softly, Kelly asks for two cards, and draws lucky - he's made his three-of-a-kind Jacks hand. In fact, he often makes these kinds of hands, and yet he has won the least amount of money in these games of anyone at the table. It's not that he enjoys losing, it's that he is far more uncomfortable winning what he believes is more than his fair share. He derives no pleasure from fleecing his friends, although it is well within his power to do so, if he wanted. And so he carefully keeps track of his bankroll, how much he has won, how much he has lost, and he never goes home with 10 percent more or less than $107. If he wins this pot, he will be over his self-imposed limit, so he puts on his most convincing "good sport frown" and says, "Aw, rats. I fold." He is no less convincing than Dombrowski, and indeed the two men are very similar in their skill sets, but where Dombrowski seeks personal gain, Donnie Baseball seeks the good of others. He will one day be General Manager of this team, and few are unaware of this fact.

It is now Ilitch's turn to draw, and the others wait in silence for an uncomfortably long time. They all know that Ilitch has actually been asleep for the past 18 hands, but no one wants to risk committing a major social faux pas by skipping his turn when, in fact, he was awake and they didn't realize it. Finally, Dombrowski furrows his brow, frowns, and nods at Kelly, who carefully removes the cards from Ilitch's hand and hands them to Brookens. "I think he said he folds," he says, and they all agree.

Brookens is the last to play because he dealt the hand. He is two cards away from a seven-high straight, but those two cards are a Queen and an Ace, and he is smelling a glorious gut-shot draw that he is sure will give him "the absolute nuts." He can let go of the high cards and attempt a runner-runner draw, or he can let go of everything but the high cards, and attempt a runner-runner-runner draw that could give him a major win here, the likes of which would be talked about for years to come. And so, as usual, he holds the runners he should have let go, and lets go of the runners he should have held. He draws nothing but garbage, of course, but this does not bother him one bit. Once he's committed to an idea, even after he knows he should have held those runners, he plays it out to the bitter end with every ounce of sincerity and excitement he can muster. Holding a lousy Ace-high hand, he begins to make the windmill motion with his arm, screaming, "Yeah-woooo-weeeee! I'm all in! I'm all in!"

In the commotion, Kelly's discarded hand falls to the floor and scatters, and as Leyland bends down to pick up the fallen cards, he drops his own as well. Donnie Baseball helps his skipper clean up the mess, and notices that his own three Jacks are now in Leyland's hand, giving him a Jacks-full-of-fours Full House. Leyland himself does not notice, because the light is dim near the floor, and he can hardly see. A beat, a breath, a quick moral decision, and Donnie decides to let the Skipper keep this one. It wasn't his fault he grabbed the wrong cards, and it's been a while since the old man has won a decent hand - he deserves to "run into one" tonight, Kelly reasons. Everything evens out in the end.

Leyland, who still believes he is playing out his pair of fours, but fiercely loyal to his hand, calls Brookens' bet and goes all in. Dombrowski breaks a sweat. He had hoped everyone would just fold when he announced his "pat hand," but the Brookens Factor has come back to bite him again. How can he fold now, after he's projected such strength? Brookens is probably holding garbage, he speculates, but Leyland is a harder read. Did he go all in against Brookens out of sheer stubbornness, or does he really have a winning hand? All eyes are on the GM, and so he continues to project strength, if only for their sakes. They need a strong leader in this organization, and he intends to be that leader, no matter what.

"I'm all in, too," says Dombrowski, and all the players still in the hand turn over their cards. Leyland lets out a stream of joyful expletives that momentarily rouses Ilitch from his sleep, and proceeds to leap up from the table and do his "moonwalk" around the room. Donnie Baseball laughs and claps his hands for his Skipper, while Brookens stares at the table in disbelief, quietly vowing to make that exact same play next time, and the next time, and the next, for as many times as it takes to prove that he does have winner's instincts. Dombrowski shakes his head, momentarily annoyed, but easily shrugging it off. He knows he took a risk on that final deal, and he knew it probably wouldn't work, so it doesn't bother him too much that it didn't actually work. He also knows that his risks usually pay off more times than they cost him, so this game is just one of many that will ultimately lead him to finally winning his money back from Leyland.

The only thing that bothers Dombrowski is that his bankroll is dipping dangerously low. He may not have enough to sustain his play through the swings of the next week. No matter. He knows that when he's down to his last resources, he can always hit up "Mr. I" for a quick shot of cash. Money may not be able to buy you happiness, he reflects, as he watches Leyland continue to moonwalk while trying to light another cigarette, but at least it can keep you in the game.