The 20 Craziest Bets I’ve Made (One Isn’t True) — Guess Which One....

Other Oct 13, 2020

In January 1971, I made my very first sports wager.

I remember the game all too well because it was my first loser.  I lost $1.

I’ve been chasing that buck ever since.

Back last year during football season, I attended a party with a motley group of professional sports bettors.  We were discussing the biggest and craziest sports bets we’d ever made.  As you can imagine, some great stories were told.  I wish I could write about them in an article, but the stories belong to some sharps who are pretty well known in the gambling business, including people you may have heard of.  So, I don’t want to blow anyone’s cover or reputation.  Instead, I’m writing today’s column entirely on my own because, you know, I have no shame.

The previous discussion got me to thinking about the biggest and craziest sports bets I’ve made.  I decided to make a list.

Here’s my 20 most unusual wagers over 50 years.  Each and every one of these events is true — except for one item.  19 are true.  1 is false.  Can you guess which bet didn’t really happen?


—– I bet $39,000 on a Super Bowl game.

True: In 2008, I had multiple bets riding on the New England Patriots with pointspreads at -3, -3.5, and -4, as well as several money line wagers.  The Patriots were a perfect 18-0 going into the game and I had bet the “AFC to win the Super Bowl” prop back in November at multiple sportsbooks.  I pounded the AFC $2,000 and $3,000 at a time until I was out of cash and the total damage came to $39,000.  The Patriots opened up that game as 12-point favorites, and the worst number I was laying was -4.  I skipped the juicy 8+ point middle opportunity and watched in horror as the Giants pulled off a massive 17-14 upset.

—– I bet $5,000 on the second half of a college football game where I couldn’t name a single player.

True: Temple was playing Rutgers one night and it was the only game on TV.  I forgot what prompted me to step out of my usual comfort zone and bet so much on a game I knew nothing about.  Come to think of it, I can’t even remember if I won or lost the bet.

—– I bet $5,000 on the second half of a Hawaii college football game.

True: I’ve done this numerous times.  Why?  Because of the vast time zone difference between Hawaii and the U.S. mainland, Rainbow home games are televised at past midnight here in the states, so it’s always a marquee game for gambling night owls.  Hawaii games and have always been college football’s “bailout special,” especially when stuck bad.  However, Hawaii games have also been wildly unpredictable with lots of offense and scoring.  This only adds to their appeal to stuck bettors.  BTW, the halftime line is the final desperation special.  My guess is Hawaii second-half bets attract some massive volume proportional to the actual game.

—– I bet on a major league baseball game in which I was ahead 10-0 going into the top of the 9th inning and ended up losing.

True: About 25 years ago, I bet on a baseball game and was leading 10-0.  But the Philadelphia Phillies scored 11 runs in the top of the 9th against the Los Angeles Dodgers and ended up winning 11-10.

—– I once went 9-1 betting the NFL on a Sunday but didn’t make a dime.

True:  About 10 years ago, I had a dream day betting on football.  I spent the whole day sweating and cheering.  Almost every game went my way.  When checked my account at day’s end I expected to be ahead $4,400.  Come to find out I didn’t win a single game because I failed to hit the “confirm” button on my online wagering account that morning.  I wonder — does that count as nine bad beat stories, or just one?

—– I lost $4,000 on the New York Yankees versus the Boston Red Sox in the 2004  ALCS, memorable for the “bloody sock” game.

True: I wagered on the New York Yankees to beat the Boston Red Sox in the American League Championship Series and lost, even though at one point in the series the Yankees were up 3 games to none, and were ahead 4-3 in the bottom of the 9th in Game 4.  Game 6, which I considered hedging, Curt Schilling was scheduled to pitch for Boston.  From the pregame warm-ups, Schilling’s ankle was bleeding.  He could barely walk!  So, I saw no reason to hedge.  The Red Sox not only won the game due to 7 brilliant innings by Schilling, they also roared back to win the series, and then won their first World Series of baseball in nearly a century.

—– I bet $1 on Super Bowl V, won by the Baltimore Colts over the Dallas Cowboys 16-13.

True:  In January 1971, legendary quarterback Johnny Unitas was knocked out of the game in the 1st quarter and the Baltimore Colts committed seven turnovers, yet they still won!  I lost a whole buck.  That was a lot of money at the time for an 8-year-old who didn’t have a dollar.

—– I once bet $7,000 on an NFL preseason game.

True: In 2016, the Los Angeles Rams played their first home game back in California after the franchise spent nearly two decades in St. Louis.  That first game back was a total sellout.  I figured there was no way the Rams would blow that game.  I got lucky.  I won the wager despite being down by three scores at halftime.

—– I once bet every college basketball team on the board teased with one NFL game — with every dollar of my net worth at the time.

True: One wild and crazy Saturday, I bet all 186 college basketball teams on the board (good for dozens of 8-point middles) and teased them all with the Monday Night Football game — with every dollar I had.  The MNF game won and I cleaned up.

—– I collected a $5,000 casino chip on a winning bet (from another gambler) but ended up unable to cash the chip.

True: Back in 2007, I had a $5,000 casino chip confiscated by the MGM when I tried to cash it at the casino cage.  I was out $5,000 (and to this day have never gotten my money).  Now, that’s a bad beat.  [MORE DETAILS HERE]

—– I bet $500 on a soccer match between two Greek teams with unpronounceable names and lost within the first three minutes.

True:  While working in London, I came across info on an obscure Greek soccer match (insert punch line here) but lost my bet right after the game started because I bet UNDER 2.5 goals.  The score was 3-0 after just three minutes!

—– I once bet on Ghana against the United States.

True: In a 2010 World Cup match between Ghana and the U.S., I faded all the money coming in on the Americans and bet the better soccer team from Africa.  I made what for me was a small fortune.  Thanks, Ghana.

—– I once bet on a dog show.

True:  A few years ago, the annual Westminster Kennel Club Dog Show was featured as a betting option at one of my offshore sportsbooks.  The site allowed wagering by dog “group.”  That was the year the hunting/hound group was stacked with pedigree dogs, so I bet the hunters and hounds.  The Beagle won.  Woof!  Woof!

—– I almost lost my two cars gambling at a bowling alley.

True: At a bowling alley years ago, I bet my two cars on one “impossible” shot (the infamous 7-10 pin split)…..which nearly ended up costing me both cars (she nipped the 7 pin, which spun across the lane but didn’t quite tip over the 10 pin).  I sweated my ass off for about five full seconds.  Thanks, Amanda — for missing the shot and not making me ride a city bus for the next year.

—– One time, I went 1-14 betting on basketball games in a single night.

True: I bet each game for $1,100.  Total loss in one night = $14,400.  Ouch!  Aside from the Super Bowl loser, that was my worst betting night ever.

—– I teased the entire NFL card with one team multiple times.

True: Okay, this one’s way too easy.  Everyone who follows my weekly picks here at the site during football season knows it’s true (Sick Brag:  6 out of 8 winning seasons, and ahead overall after more than 1,400 wagers!).

—– I once lost $4,000 betting on a presidential election.

True: I bet $4,000 on Sen. John Kerry versus incumbent President George W. Bush to win the 2004 election.  Not only did I lose; the country lost.

—– I once played in a poker game during a revolution while shooting was going on outside.

True:  I was stationed in Bucharest during the fall of Nicolae Ceausescu.  The Romanian Revolution happened in December 1989 and things didn’t calm down until the summer of 1990.  After a while, one becomes desensitized to violence and danger.  Some embassy staff continued playing in a live poker game while someone was shooting a machine gun out of a helicopter flying overhead (besides, the poker game was really good).

—– I once lost a bet on a chicken commercial.

True: I bet $100 against someone who absolutely insisted that professional poker player Gavin Smith (RIP) had once appeared in a Kentucky Fried Chicken commercial.  I knew Gavin and figured if this happened I surely would have known about it.  We shook on the bet and I immediately called up Gavin.  Well, shit!  I lost.  Gavin Smith really did do a chicken commercial.

—– I once bet on an execution.

True: I wagered $200 against gambling math guru Bill Chen’s $500 that Iraqi dictator Saddam Hussien wouldn’t be executed by hanging.  I lost.  Oh, and so did Saddam Hussien.  He lost bad!

—– I once bet a three-team parlay.

True or False?

Okay, can you guess which wager didn’t really happen?

The (in)correct answer is —– “I once bet a three-team parlay.” In my entire betting lifetime, I have never once made a 3-, 4-, 5-, etc. team parlay.  Not even once.

Gee, I wonder what kind of price I could have gotten on a 3-teamer — George W. Bush to win, Gavin Smith appearing in a chicken commercial, and Saddam Hussien to hang?

That bet was a lock!