Exactly two years ago, before I joined the hallowed ranks of The Action Network, I sat in a drab office building. It was a beautiful Milwaukee Monday. Things were slow. But even before I stepped into the building that morning, I knew I wouldn’t be shackled to a cubicle all day.
Like a lot of America’s gamblers, my boring white-collar appearance belied my constant search for a nice midday sweat. And true to form, early that morning I’d made an unusually large bet on an afternoon baseball game, one big enough to deserve my full attention.
Emails? Expense reports? Small talk about Randy’s fishing trip? These would have to wait.
The Little League World Series was calling my name.
The Long Con
I immediately started laying the groundwork to leave early without arousing suspicion. By 9:30 a.m. I subtly complained of clammy hands and other vague ailments noted huckster Ferris Bueller once called “good, nonspecific symptoms.”
Looking the part was just as important. When I’d pass an empty conference room, I’d slip in and knock out some pushups to keep my skin flushed with an unsavory sheen. Not one, but two co-workers asked me if I was feeling all right, so I knew it was time.
There was a bowl of fruit in the office’s lunch area and — with this being Wisconsin — that fruit went largely untouched. I took an orange, peeled it and coyly slid the segments into my pockets.
I casually strolled to the bathroom. No one else was in there, so I ducked into a stall. I removed the orange slices from my trousers and crouched over the toilet, waiting for a co-worker to enter. And as soon as that door opened, I threw those slices to their watery grave as hard as I could and attempted the most convincing faux vomit I could muster.
Panting like a werewolf, I flushed the evidence and emerged, barely making eye contact with my co-worker on my way out the door. I didn’t make a habit of this kind of chicanery. It’s nothing if not distasteful. But seasoned gamblers know the importance of priorities — and they know themselves. Plus, I knew if I stayed at work, there was a better chance I would spend the afternoon hyperventilating under my desk instead of doing actual work.
I limped into my boss’ office to explain the situation. She was a real stickler, but a Monday afternoon in the middle of August is a strange time for anyone to fake sick. Plus, I had a corroborating witness.
She played right into my citrus-scented hands; I was a free man.
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There was a divey sportsbar nearby. It was the perfect spot to catch a game incognito. I’m sure the bartender saw my “GO BILLS” license plates pull up and knew a born loser was about to walk in. That’s probably why he seemed unsurprised when I asked him to change the channel on the TV.
Me: You guys don’t even have ESPN on? The New York game’s on. What kind of sports bar is this?
Bartender: It’s 2 o’clock, champ. Yanks are off today, Mets don’t play for seven hours. There’s nothing on. And why are you so sweaty?
Me: Listen, it’s the Little League World Series. Opening round. … [leaning in] I got a lot riding on these kids. And I’ll take two Buds.
He gave me a look that mixed disbelief and pity in equal amounts, like Jim Mora being asked about the playoffs. But it arrived with a couple beers and a channel flip to ESPN just the same.
Now, I’m aware the Little League World Series isn’t typically a hotbed for aggressive action. Some of you were probably unaware you could even bet on it. Even more of you might find it distasteful. But perfectly legitimate offshore books such as 5Dimes have been taking bets on it for years.
A Hot Tip
On the United States’ side of the bracket, the New England Region was represented by a tough Rhode Island team. It opened against the Mid-Atlantic, represented by Maine-Endwell, the first team from upstate New York to make it to the dance in nearly 40 years.
I am a Rochester native, but regional pride wasn’t what sparked a Super Bowl-level bet on a high-stakes showdown of tween boys.
No, my withered gambling heart was set on our nation’s purest amateur athletic tournament for the oldest reason in the gambling universe — a reason as old as gambling itself: I received a hot tip.
My mother was born in the small hamlet of Endwell, like her mother before her. She attended Maine-Endwell High School (go Spartans!), and her side of the family has lived in the area since arriving from Italy almost 100 years ago.
I heard through the grapevine that Maine-Endwell’s star pitcher, Michael Mancini, was the real deal. The kind of dominating man-child few teams can boast each year. And once these guys make a start or two on ESPN, the market corrects, so I trusted my guy in Susquehanna Valley and made my move.
Maine-Endwell opened as a heavy -175 favorite, but also as a delicious even-money on the run line. The over/under was set at nine, a number that seemed far too high. I dropped six units on the run line, plus another two on the under. My hands gripped the bar rail during a whispered prayer for Mancini, and I watched the action unfold from South Williamsport, Pennsylvania.
Never In Doubt
Luckily, the game unfolded as I’d hoped. Mancini was as overpowering as promised, and my grip on the rail started to loosen. The bar remained blessedly empty. The bartender was even kind enough to be a team player (maybe he just wanted a tip off my Mancini money) and pretended that a bona fide grownup shouting things like “Hit the cutoff, Jayden! Fundamentals!” was normal.
The game was cruising to a close, and M-E held a comfortable 7-0 lead with only two outs to go. The run line seemed assured, and the faces of those young, downtrodden Rhode Islanders had me certain the under was going to get across the line, too. But literal and metaphorical storm clouds rolled in, and a 35-minute rain delay dampened my expectations. These were kids, after all. A long break with a big lead wasn’t good for my boys’ collective focus.
Play resumed, and Mancini had given way to the team’s closer. Soon, Rhode Island runners were on the corners, and I’d gotten the sweat I’d hoped to avoid all afternoon. A long pop to center followed, an easy sacrifice fly. But as color commentator John Kruk reminded the audience, no need to risk it. Youth Baseball 101: Never make the final out on the basepaths.
I nodded along to Kruk’s sage advice, just one out away, with a slim one-run cushion for the under. The next batter sliced a single to left, and whether it was slick conditions or a laissez faire attitude brought on from the rain delay, the right fielder missed fielding the ball completely. Both runners scored; my under was toast. But the adolescent batter found himself too excited on the basepaths. He ignored Kruk’s advice and his own third base coach and went full steam ahead toward third. He was thrown out easily. Game over, 7-2.
I celebrated my run line win like a March Madness buzzer-beater, buying shots for the one other patron who’d walked in. I felt grateful the under pushed.
Even before the score had been updated on the screen, ESPN cameras captured the Rhode Island third base coach — a volunteer and father of one of the players — as he kept his arms up in a clear “stop sign” signal. The runner looked at him, visibly ashamed. Not something you’ll see on Sunday Night Baseball.
So as summer slowly draws to a close, betting the Little League World Series is my favorite sign that the end of the long gambling winter is coming. It is the perfect preparation for the robust harvest season that follows. You don’t want to enter football season cold. Even Little Leaguers know the importance of a warmup to avoid getting hurt. Always remember the fundamentals.