Five of the biggest long-shot winners ever

Apr 14, 2010 |

We all want to be filthy rich but too many of us don’t use enough imagination with the daydream. Winning the $50 million state lottery? Come on. There are cooler imaginary scenarios to collect major coin.

My favorite way? The Biff Tannen way. Yes, the same Biff from Back to the Future Part II.

For those of you who can’t remember, Biff used a sports almanac from the future to earn his fortune. And it’s not just the money. Biff was considered the world’s best tout because he knew the outcome of all the big sporting events.

Hey Butthead

He completed the Scarface trifecta: money, power and the woman (Marty McFly’s mom, Lorainne).  

These five long shot bets could help create your evil empire if you do ever get a hold of a DeLorean time machine.

St. Louis Rams win Super Bowl XXXIV (300-to-1)

The "Greatest Show on Turf" would have never been born if Rams coach Dick Vermeil would have gotten his way. After a 4-12 campaign in 1998, Vermeil was still in love with quarterback Tony Banks. That’s the same Tony Banks, who reportedly skipped the team flight home after an embarrassing 14-0 loss to Miami and missed practice because his dog died.

In a rare occurrence, Mike Martz, who at the time was the Redskins quarterback coach, was the voice of reason. When the Rams offered him the chance to become offensive coordinator, Martz refused unless Banks was gone and Green was signed.

Martz got his way and then some.

In the offseason, the Rams acquired Marshall Faulk from the Colts for a second and fourth-round pick, signed Green and drafted wide receiver Torry Holt out of North Carolina State in the first round.

So expectations were up, until Green suffered a season-ending knee injury on what most perceived to be a dirty hit by Rodney Harrison in a preseason game.

That left Vermeil with a backup quarterback out of the Arena League named Kurt Warner. Expectations were down and it seemed laughable when Vermeil said, “We will rally around Kurt Warner.”

But Vegas wasn’t laughing when Warner led the Rams on a bookie-killing run that saw them go 13-3 straight up and against the spread.

They capped off the run with a thrilling 23-16 victory over the Tennessee Titans in Super Bowl XXXIV. On the game’s final play, Titans’ receiver Kevin Dyson was tackled one yard short of the end zone by Mike Jones.

1991 World Series: The books’ worst nightmare

Featuring a pair of worst-to-first teams in the Twins and Braves, the bookies were going to lose some cash either way. Before the season, both the Twins and Braves were between “300-to-1 and 200-to-1” to win the World Series, according to sportsbook manager Jeff Stonebeck of the Las Vegas Hilton.

And why wouldn’t they be? Before 1991, no team had ever won a pennant after finishing last the previous season. In 1990, the Twins finished 14 games under .500 and were 29 games out in their division. The Braves were worse, losing 97 games in 1990.

Naturally, the Twins and Braves followed up dreadful season by stunning the baseball world by reaching the World Series and crushing sportsbooks everywhere.

1991 Twins

Greece 2004 UEFA Euro (150-to-1)

Having never won a match at a major tournament, few football fans were eagerly jumping a Greece bandwagon that, frankly, no one knew even existed. Hence, the plump odds.

It will be a while before Greece backers enjoy that kind of odds again. The Greeks turned Euro 2004 into a coming-out party. They knocked off favorite France and twice beat Portugal, including in the finals.

The Cinderella run to the title sparked an interest in Greek football and earned global respect. Greece shot up from 35th to 14th in the FIFA World Rankings, one of the biggest jumps in a single month ever.

Tampa Bay Rays 2008 American League Champs (125-to-1)

In perhaps the most rewarding name change in history, the Tampa Bay Devils Rays became the Tampa Bay Rays in 2008 – and won the American League pennant.

Since its inception in 1998, Tampa Bay seemed destined to become the Clippers of MLB. The Rays finished last in nine of their first 10 seasons. In 2007, the Devils Rays were the worst team in baseball and were stuck in the toughest division, the AL East.

But, while they were getting trounced in their infant years, they were also feeding off greedy heavyweights who were willing to give away young talent to win immediately. In 2008, all that young talent blossomed. They stunned baseball by winning the division and knocking off the mighty Red Sox to reach the World Series.

“At the beginning of the season, the Rays were 125-to-1 to win the American league and a whopping 300-to-1 to win the World Series,” said oddsmaker Richard Gardner. “While the Rays went on to win the AL that year, things could have been much worse if they went on to win the World Series. It is still the biggest loss on futures that I have seen in my time in the industry.”

1913 Kentucky Derby

At 91-to-1, Donerail is the biggest long shot to win in Kentucky Derby history. Donerail paid $184.90 on a $2 bet, while setting a track record of 2:04 4/5. His career earnings only amounted to $15,156.

1991 Twins


Certainly, some of you expert bettors out there have used your expertise to cash on a big long shot. Maybe you had Buster Douglas at 45-to-1 against Mike Tyson. Or maybe you had eighth-seeded Golden State to knock off the Mavericks a few years ago.

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