Through office pools and bracket contests, the NCAA Men’s Basketball championship tournament turns millions of casual fans into gamblers each and every year.

But serious bettors also see the bracket as a golden opportunity to beat the house. With 68 teams in the tournament field, but only a dozen or so legitimate contenders, March Madness is usually a mismatch made in heaven for the chalk.

The disparity between elite teams and mid-major programs can be so profound that heavy bettors are often prompted to pound Las Vegas sportsbooks with huge parlay bets linking top seeds.

And why not?

Entering the 2018 NCAA Men’s Tournament, a #16-seed had never beaten a #1-seed, compiling an 0-132 record of pure futility. With numbers like that on their side, sharp bettors flock to Sin City every spring to back favorites in what should be surefire moneyline parlays.

As reported by the Las Vegas Review-Journal, the Wynn sportsbook took in $90,000 on a three-team moneyline parlay before the tournament’s opening round. The bettor could only win $10,000 in profit, but with #1 Xavier toppling #16 Texas Southern (103-82), #2 North Carolina knocking off #15 Lipscomb (84-66), and #2 Cincinnati downing #15 Georgia State (68-53), the five-figure stake was never really at risk.

Conversely, the same newspaper caught wind of a similar bet that didn’t work out so well.

The Wynn sportsbook took a $100,000 three-team moneyline parlay which would have produced $26,000 in profit. The bettor backed #2 Cincinnati in the Bearcats’ aforementioned win, plus #3 Michigan State in a 82-78 sweat over #14 Bucknell.

But when #4 Wichita State – a team that closed as 13.5-point favorites – suffered a shocking 81-75 upset at the hands of #13 Marshall, the six-figure “lock” went down in flames.

In a downsized version of the lopsided risk to reward ratio, another bettor plunked down $20,000 to win $870 on a three-team moneyline parlay through Las Vegas sportsbook operator CG Technology. That ambitious bet involved the Tar Heels’ thrashing of Lipscomb, along with #2 Purdue’s easy 74-48 walkover against #15 Cal State Fullerton.

Unfortunately for the bettor in question, history and probability combined to deal their ticket a fatal blow.

The third leg of the $20,000 parlay required #1 Virginia – a juggernaut which topped the tournament’s overall seeding with a 31-2 record – to beat #16 University of Maryland Baltimore College (UMBC).

While the Cavaliers were compiling a pristine record against top tough ACC foes like Duke, Clemson, and North Carolina, the Retrievers of UMBC went 24-10 for a second-place finish in the America East. Only a last-second three to end the conference championship game put UMBC through to the tournament, and the ragtag bunch getting 20.5 points wasn’t expected to last longer than 40 minutes.

Rather than tuck their tails though, the Retrievers put on a show for the ages, dismantling the Cavaliers in a 74-54 stunner.

And with that, one bettor’s $20,000 gambit was gone in an instant.

As documented by Covers, Alabama native and Venetian sportsbook bettor Mikal McCulley was on the other side of the improbable upset.

McCulley took a (+2000) moneyline flier for $100, turning his UMBC ticket into $2,000:

““We’re in chatrooms with a bunch of guys who are sports handicappers. We go over plays every night.

When the bracket came out, we liked UMBC. We’ve been anti-Virginia winning the title since the beginning of the season, because of its style of basketball. It leaves no room for error.

Virginia was going to have a rough time making it through the tournament.”

That wasn’t even the largest win hauled in by the Retrievers. As reported by Jason Simbal on Twitter, CG Technology took in an $800 moneyline bet on UMBC at (+2000), with the lucky winner bagging $16,000 in profit.

Jonathan Zaun

One of Gamble Online's first dedicated reporters, Jonathan has spent well over a decade reporting on the gaming industry. While breaking legal news is his main area of expertise, Jonathan is an avid blackjack player & strategist who follows professional poker closely.

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