Small Bets. Impossible Odds. HUGE WINS. How Do They Do It?

Posted on January 8, 2020 - Last Updated on January 11, 2020

What a collection of golden nuggets from the sports-wagering world. These are the craziest sports bets of the week.

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Gamblers employed varied parlaying methods to dent the Wager Wonderland scoreboard during the holidays and early January. Their creativity knows no bounds and for some bettors, the sky was the payout limit.

Hitting the Board

Our most recent Cha-Ching Crop spans several entities. Some skillful player props emerged via DraftKings. Some FanDuel winners provided the uncanny knack of selecting specific win margins. 

There’s also a heartwarming story at PlaySugarHouse involving a retired couple nailing $125,000 in a season-long online contest where they just picked NFL Winners.

Let’s take a look at some of the craziest sports bets that actually paid off.

Turning Garbage Into Gold

On Jan 4, a DraftKings user placed a $25 free bet on an 11-leg parlay with ticket odds of +63940:

It paid out $15,986.25 when all 11 legs hit!

Here’s The DraftKings “Box Score”

  1. Nikola Jokic to record a double-double
  2. Domantas Sabonis to record a double-double
  3. Darius Garland over 3.5 assists
  4. Celtics -2.5 vs. Bulls
  5. Pistons -3.5 vs. Warriors
  6. Pelicans/Kings over 214.5 points,
  7. Raptors/Nets over 206.5 points
  8. Joe Ingles over 2.5 3-pointers made
  9. Luka Doncic over 31.5 points
  10. Titans +14.5 vs. Patriots
  11. Vikings -2.5 vs. Saints  XXX

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A combo package of smart and genius was used to garner this collection.

The first piece of intelligence was using one of the many free bets DraftKings uses to entice bettors, once they have signed up and funded their accounts. This was a $25 freebie. Smart. Just like a free play in the NFL encouraging a deep pass, this freebie encouraged a multi-leg parlay.

The genius?

craziest sports bets

How about taking the Minnesota Vikings as an adjusted -2.5 against the New Orleans Saints, who were favored by 7.5.? Wow!

He chose the alternate line being 10 points harder on the Vikings, and that’s one reason the ticket paid so well. 

This bettor was one of the few in America to make the Vikings, the biggest underdog of the weekend, a favorite.

Another timely selection was moving the Tennessee Titans line against the New England Patriots from +5 to +14.

  • The Titans won outright.

Heineman Family’s Football Fairytale

We champion Wager Wonderland as a fraternity of gamblers, many of them serious, who make multiple bets, take calculated leverage and relish the rush of making a stab.

And then there are the Heineman’s…

We can’t leave them off the list of the craziest sports bets. Right out of the Hallmark Channel, retired construction worker Gary Heineman and his wife Roxanne stumbled into contention during a season-long online contest.

  • The Canonsburg, Pa. couple played one entry of $150 into the state’s first-ever online Vegas-Style pick-em contest and won $125,000.

    Gary Heineman Roxanne football winners
    Gary Heineman and his wife Roxanne

“We are just working-class people and that’s a lot of money,” said Gary, a 57-year-old.  “We are so excited we just can’t believe this.  It’s life-changing.”

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How did they do it?

 About midway through the season, they found themselves in eighth place. So Roxanne decided to roll up the sleeves and handicap. She began researching the odds and looking at betting sites to determine where public sentiment was.

Can you picture this?  Dinnertime conversation shifting from immediate family and nephews to which NFL dog was due to bark.

The Heineman’s began taking a shot with underdogs, a must in this format. Playing it safe with favorites might produce a top 10 finish, but only the results nobody sees coming bears fruit.

Non-playoff teams like the Chicago Bears, Cincinnati Bengals, and the New York Jets came into play late in the season.  And in the decisive Week 17, they all triumphed.

Gary Heineman Roxanne football winners

The Bears, in fact, won on the last play of the game against the Minnesota Vikings in the final week. The one-win Bengals made it two against the Cleveland Browns and the Jets won in Buffalo, which was resting its players for the post-season. Those picks, combined with others, helped Gary gain 161 correct selections, just two ahead of the runner-up.

The couple started shaking when they got the call that they’d won the grand prize.

Overall, 500 top pick winners were paid out cash winnings at the season’s end, in addition to the top weekly score on each site earning $2,500 each week. The entrant with the most incorrect picks also received a $2,500 payout.  In all, $500,000 was paid to entrants.

And what’s the first thing Gary did with the money?

He upgraded Roxanne’s wedding ring.

Smart man. That may have been his best selection of all.

Wager Wonderland takeaways from their fantastic story:

  1. Never be afraid to bet dogs
  2. Listen to your wife
  3. You can’t win if you don’t play

More “Conventional” Riches

  • On Friday, December 20, a FanDuel customer placed $40 on a 6-leg parlay on the NBA which paid out $34,412.  The parlay focused on Win Margins of the NBA, with one moneyline.

Here’s the box score

 Celtics 11+ Win Margin @ +110

 Pacers ML @ -215

 Heat 11+ Win Margin @ 105

 Cavs 1-10 Win Margin  @ +210

 Raptors 1-10 Win Margin @ +175

 Mavs 11+ Win Margin @ +1500

This one produced not only the magic of compounding but expounding on a hunch. This bettor thought the Dallas Mavericks could win by more than 11 points in Philadelphia against the 20-9 Sixers.

Quite a leap of faith. And quite a landing as the Mavs took out the Sixers 117-98, as a road team.

That was the pure genius of this wager, enabling the huge payout. The Mavs had odds of 15-1 to cover that spread. They deserved to be that long because Philadelphia had only one home loss, two nights earlier by four points, to the Miami Heat.

A core, but rarely-expressed strategy, is being fortunate enough to make half the correct selections on a couple of multi-leg cards and then alternating the others. Craziest sports bets indeed.

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Twenty Gets You Twenty-FourGRAND

 On December 22, a FanDuel customer placed $20 on a 10-leg parlay on NFL and college basketball which paid out $23,985.  The parlay focused on spreads, point totals and moneyline. Here’s how it looked.

 Nevada 1st Half ML @ +215

Hofstra -9.5 @ -115

 Under 151.5 (Chicago St. vs Ind. St) @-110

 Over 41.5 (Giants vs. Redskins) @ -110

 Falcons -7.5 @ -105

 Davidson +3 @ -105

 Iowa State -18 @ -110

 Ravens -10 @ -110

 Dolphins ML @ +106

 Saints -2.5 @ -105

It wouldn’t constitute drama unless it commanded one of the most colossal collapses in NFL history.

One of the legs was the Miami Dolphins on the moneyline against the Bengals, as a pick-em. Looking great when the Dolphins led 35-12 with 11 minutes left. Still looking good when they were ahead 35-19 with 30 seconds to go.

But then came the sequence that makes gamblers swear off betting _ for awhile.

The Dolphins gave up a touchdown and two-point conversion with 29 seconds left. Bad enough. 35-27. But then the Bengals had to go for an onside kick, there had been only seven made all year, they wouldn’t convert one now, right?

They did.

And as the Dolphins sagged, the Bengals marched down the field and scored a Hail Mary on the final play of the game. Dolphins still led by two. Still a winner. But then they surrendered the game-tying two-point conversion after time had expired.

Think of all that. Five bad things happened to Dolphins bettors in 29 seconds. At the hands of the worst team in the league!

Impossible. It would have been one thing to squander a small bet on this. But not almost $24,000.

The bettor then had to sweat out overtime and the Dolphins won it really late. But it ended well.

  • This bettor took Nevada on the first-half moneyline, which covered even though Nevada lost 68-63.

Hofstra covered 9.5 against Manhattan in squeaking by, 63-51

Chicago and Indiana State kept the offense down enough for the under 151.5 to shine in an 85-64 triumph for Indiana State. The total was 149, a win by 2.5, what a close shave.

The easy one was the Giants-Redskins over 41.5. The Giants nearly covered that themselves in a 41-35 win. The way the defenses played in that one and the way Saquon Barkley ran roughshod en route to a 278-yard scrimmage day made an over bettor feel joyous on an early clinch.

The Atlanta Falcons labored but covered the 7.5 against the Jacksonville Jaguars in a 24-12 win.

Davidson got three points against Loyola Chicago and doubled it with a three-point, 59-56 win.

Iowa State gave 18 but scorched Fort Wayne 89-59.

The Ravens gave 10 against the Cleveland Browns but did enough in winning 31-15.

The New Orleans Saints beat the Tennessee Titans 38-28 to cover 2.5.

Everything looked easy except for the game that WAS easy, until the end.

It’s exciting to watch betting unleashed in the legal wagering age, especially when it comes to the craziest sports bets we can find.

Good luck with those bets. Maybe the next story in our sports-betting country club will be about you.

Dave Bontempo Avatar
Written by
Dave Bontempo

Dave Bontempo, a national multi-award-winning writer, and broadcaster, writes extensively on the evolving legalized sports-wagering world. Over the past four decades, he has called fights for all major networks, authored columns for the Associated Press, Atlantic City Press, and iGaming Player. He is in the New Jersey Boxing Hall of Fame, the Atlantic City Boxing Hall of Fame and a Sam Taub Award for broadcast excellence, given by the Boxing Writers Association of America.

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