How I Won $11,500 Betting on Baseball


Alotta guys (two) have been asking me how, exactly, I won eleven grand betting on Ian Happ’s lead off home run at the start of the Cub’s 2018 season, after I mentioned that in a blog a few weeks ago about whether I got roofied in Cabo (I did).  Well, here’s the full story.

 “I’ve got $250 on Happ hitting a lead off home run,” I told the guy on my left, my new friend, who I had just met 10 minutes earlier when Jake and I found our seats.  It was an absurd wager, even by my standards, and I had to tell someone other than Jake.

The woman to my right, on the other side of Jake, overheard.  I had noticed her coming in because she was hot.  I had also noticed her two kids next to her, and her husband on the other side of them.  Oh well.

“You bet $250 on this batter hitting a home run?” Hot Mom asked, looking at me funny.  “What are the chances of that happening?” she continued, laughing.  Everyone was in a great mood in the Florida sun, since the Marlins had opened the stadium roof.

“Funny you should ask,” I answered, leaning over Jake to talk to Hot Mom.  He bristled, looking at me funny, like he always does when I talk to hot women who aren’t his mom.

“The odds are 45 to 1,” I told her, loudly, as Ian Happ, the Cub’s center fielder, strode to the plate.

“Wow, that would pay a lot,” she said, laughing, probably attracted to my reckless daring, in my warped mind, at least.

“Where do you even place a bet like that?” my new friend to my left asked, laughing at the ridiculousness of betting that a home run would be hit by the first batter.

“The String,” I answered, turning my attention to the game, as Jose Urena of the Marlins delivered the first pitch of the 2018 Major League Baseball season.

“The String” is 10 or so of my degenerate friends on a text chat group that we call, appropriately enough, the String.  Mongo started the String many years ago with his golfing buddings from the Chicago suburbs.  I don’t golf much, but the guys on the String invited me to join after I met them on a skiing and gambling trip a couple years ago.

We text constantly on the String, about anything and everything.  Topics of discussion include sports, politics, work, drinking, planning for the next Vegas trip, their golf club, our kids’ fuck ups, etcetera.  The String is pretty much an ongoing conversation with everyone chiming in with whatever is on his mind.

We do a lot of gambling on the String, and we will bet on anything.  Sure, we bet on the usual stuff, like the winners of ball games and pools for March Madness, etc.  But we also sometimes make shit up, proposition bets, if you will, and see if someone will take the bet.  That’s how the $250, 45 to 1 bet that Happ would start the season with a home run came about.

My son Jake and I were in an Uber on our way to the game when I thought of the bet.  We were on his Spring Break, his last high school Spring Break before he graduated this past June.  Jake originally didn’t want to do anything for Spring Break, because he is kind of a mope sometimes, but also because he has a girlfriend and didn’t want to leave town.  He wouldn’t admit that was the reason, but I knew.  Anyway, I had trouble convincing him to do anything for Spring Break, which was pissing me off.  It is kind of my Spring Break, too, right?  Then I had a great idea.

“How about we go to Florida for Spring Break, and we can go to the Cubs-Marlin season opener, and also see Uncle Kenny,” I proposed.  Jake is a big sports guy, and a huge Cubs fan, so I knew this would convince him.  He also likes my Uncle Kenny, and hearing Uncle Kenny’s stories.  Like the time Uncle Kenny hit 5 home runs in one day, 3 right handed and 2 left handed.

“Yea, that would be cool!” Jake replied, enthusiastic about something for a change. 

Finally, we had a plan.  Since Jake had a baseball game on Tuesday night, I made reservations at a hotel on the beach in Fort Lauderdale starting Wednesday, and secured Cubs tickets for the Cubs-Marlins game on Thursday.  We also planned to meet my buddy Slim and his dad at the Cubs game on Friday, and my Uncle Kenny for some jai alai gambling on Saturday.  We not only had a plan, we had a great plan.

So anyway, on our way to the game on Thursday morning, I was texting with my idiot friends on the String, per usual.  SeaDick sent the Cubs lineup, like always does when it comes out a couple hours before every Cubs game.  I noticed that Ian Happ was leading off, and had heard that Happ had been hot in the preseason, hitting several home runs to start the game as the first batter in the lineup.  Hmmm.  That could be an interesting bet, I thought.

“What kinda odds can I get on Happ lead off HR?” I texted to the String.

SeaDick replied “Hmm.  Standby.”  SeaDick is a huge Cubs fan, and, I am sure, knew that Happ had been hot in the spring training games.  I am sure he was doing calculations, maybe even checking online to see if there were any published odds on this exact proposition bet.

And then, out of right field, Mongo replied “I’ll give you 45-1, with a $250 minimum bet.”

“Holy shit!” I thought, those are great odds.  I was thinking that the odds were probably in the 20 to 1 range, and Mongo was offering much better than that.  But there was a catch.  And this was a classic Mongo move.

Mongo was offering great odds, but I had to bet a minimum of $250.  Mongo’s thinking was that he would surely win, and when he did, he wanted substantial money out of the bet.  $250 was real money.  He didn’t want me betting $10 or $20, so that he wouldn’t win that much when I lost, but he was still exposed to a substantial payout if the impossible happened.  Plus, the $250 was a personal challenge.  He was basically saying, Pipes, if you don’t have the nut sack to place a real bet, with real money, then I don’t want your bet, you pussy.

I was now the one in a corner.  I had proposed the bet, and could not now back down because Mongo had made it too expensive.  What would that say about me as a person?  Ok, maybe it would say that I was reasonable and had some common sense, but that is not how guys think in a situation like this.

“How many lead off home runs did Happ have in spring training?” I asked Jake.

“I don’t know,” Jake answered, “something like 7 or 8.”

“How many games do they play?” I asked him.

“20 or so,” Jake answered.  I had no idea if he was right, but I trusted him.

Jesus, I thought to myself, that’s like 2 to 1 or 3 to 1.  And Mongo would give me 45 to 1!  But then again, the Marlins would be starting their best pitcher, not whoever was basically throwing batting practice in spring training.  However, I could not think of a single Marlins pitcher, so the pitching couldn’t be that great.

“Who is the Marlin’s best starting pitcher,” I asked Jake.

“No idea,” Jake replied.  So I was good on that point.

Time was also critical here, because SeaDick could come back at any second with some reasonable odds in accord with reality.  But, he probably wouldn’t, because, like me, he could see that Mongo was out over his skis on this one, and would probably keep any info to himself so that the bet got placed.  But even if SeaDick didn’t say anything, one of the other guys could chime in at any second, and say something about all of Happ’s preseason home runs, and ruin everything.  With that info, which Mongo almost certainly did not know, Mongo would pull the offer.  There was no time to waste.

“Booked,” I replied on the String.

Mongo didn’t expect that.  “I should have figured in Marlins pitching,” Mongo texted back, clearly regretting the bet on his end.

“I think those odds are about right,” I texted, facetiously.

“I just bet Mongo $250 that Happ leads off with a home run,” I told Jake.  “At 45 to 1 odds.”

“Wow,” Jake said, “how much would that pay you?”

I had just done the math for the first time on my iPhone calculator, and turned the phone to show Jake.  $11,250.  Jake just looked at me with wide eyes.

The traffic was ridiculous and Jake and I barely made it to our seats in time to see the first at bat.  I had not told Jake, but our seats were in the first row, right on the Cubs dugout where the players left the dugout to go to the plate.  As we made our way to our seats next to Hot Mom and my new friend, Kris Bryant and Anthony Rizzo were about 20 feet away, taking practice swings.  Ben Zobrist was right in front of us, standing in the dugout next to Joe Maddon, the Cubs manager.

“Nice seats Dad,” Jake said, shaking his head and smiling.  Even though we were in Marlins Park, almost everyone around us was a Cubs fan.

As you probably know, Ian Happ drove Jose Urena’s first pitch into the right field stands for a leadoff home run.  Everyone went nuts, but none more so than me and Jake.  We were high fiving everyone, including my new friend and Hot Mom.  As Ian Happ came back in the dugout, I thanked him personally, screaming at him “You just won me eleven grand!”  We have this all on video if you don’t believe me.

Word quickly spread that I had a bet on a leadoff homer.  “Looks like you are buying the beer!” a guy a few seats down suggested, laughing, and high fiving me.  I don’t take comments like that lightly and a couple innings later waved down the beer guy and bought a beer for anyone in our section who wanted one, including the 19-year-old kid next to me.  That was not cheap, but it was sand off the truck, as we say.

“Looks like you paid for these seats,” Jake observed.

“That paid for the whole trip,” I corrected him.

Mongo was not happy with this development, of course, but he took it like a man.  He did demand that I give him a $250, 45 to 1 bet, so that he had a chance to win his money back. 

He proposed a $250 bet on the White Sox winning their first 5 games, and demanded odds of 45 to 1.  The odds should have been something like 32 to 1, but I gave it to him anyway, to give him a chance to win his $11,250 back.

The White Sox started off hot, and won their first two games against the Royals.  I was starting to sweat, a little anyways.  The White Sox lost their third game to the Blue Jays, earning me another $250.

And that is how I won $11,500 betting on baseball.

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