Drake’s Dad and Other Big Sports Betting Winners

Sportsbook Moneyline, Drake's Dad Dennis Graham, 50 Cent, Money
One of the most exciting aspects of sports betting is that anybody can win big, amateur or pro.

The catch, though, is that you either have to bet long odds or risk lots of money. But some bettors have proven that the risk is worth the reward in either case.

Several sports bettors have gotten rich off one or more successful wagers. Even Drake’s dad recently netted six figures with a huge betting win.

Below, you can see more on Dennis Graham’s story, along with other gamblers who’ve won big with sports gambling.

Dennis Graham

Dennis Graham is known first and foremost as the father of Aubrey Graham (a.k.a. Drake). While his son may be one of the world’s biggest hip-hop icons today, Dennis was the first musician in the family.

Graham started playing drums in 1962. He used a makeshift setup that included round tin tubs that people used to bathe in.

James Brown’s drummer gave Dennis his first reel set of drums. This gift helped pave the way for his eventual career, which included drumming for Jerry Lee Lewis.

In more recent years, Graham has started a hip-hop career of his own. He released his first single in 2017, “Kinda Crazy”. Dennis was also featured on the cover of Drake’s 2017 album, “More Life”.

What does any of this have to do with sports betting?

Well, Graham recently wagered $100,000 on the Toronto Raptors winning the 2019 NBA championship. The Raptors were underdogs to the two-time defending champs, the Golden State Warriors.

However, Dennis wasn’t phased and decided to put a six-figure sum down on Toronto anyway. He was likely inspired to do so by Drake, who’s the global ambassador for his hometown Raptors.

Graham was rewarded handsomely when Toronto pulled off the upset, winning the series four games to two. Drake’s dad, meanwhile, pocketed $300,000 after taking the Raptors at 3-1 odds.

Sir Ride A Lot

The 2017 World Series was one of the best in recent memory. The LA Dodgers and Houston Astros went the full seven games, with the Astros pulling out the victory.

An interesting side story involving an Eastern European gambler developed on the side of the World Series. The anonymous gambler, who became known as “Sir Ride A Lot,” placed enormous wagers on the first six games.

Of course, betting big on baseball’s premiere event isn’t a story in itself. But the fact that this gambler let his winnings ride after every game is.

Los Angeles Dodgers Team

He accumulated $6 million in profits after five successful bets in five games. The logical thing to do in this situation would’ve been to pocket the multimillion-dollar win, or at least only bet a portion of it.

Sir Ride A Lot had other ideas, though. He wagered all $6 million on the Dodgers (-126) winning Game 6. His hot streak continued as LA won and his winnings soared up to $14 million.

He actually thought about risking the $14 million on Game 7. However, the temptation to keep the eight-figure fortune was too great and he stopped betting.

Haralabos Voulgaris

The first couple of gamblers covered in this post were the beneficiaries of incredible luck. But Haralabos Voulgaris (a.k.a. H-Bob) is a professional bettor who’s earned millions of dollars through skill alone.

Voulgaris’ journey towards success began in the early 2000s, when he discovered that bookmakers were setting inefficient NBA halftime totals.

Sportsbooks weren’t accounting for how fourth quarters normally feature more scoring due to foul-clogged endings. Instead, they priced each half at roughly the same amount each time.

H-Bob began taking the “over” with second-half totals and making a fortune. He’d collect millions of dollars before bookmakers realized and adjusted their strategies.

Voulgaris wasn’t done yet, though, because he developed a betting algorithm in the mid-2000s. He used this program to continue building on his fortune.

He’s since parlayed his immense knowledge of the NBA into a front-office job with the Dallas Mavericks. He also still has much of the fortune that he made by gambling on basketball.

Billy Walters

Billy Walters is another professional bettor who used his wits to win big. Walters started his professional life as a car salesman in Kentucky.

He quickly proved a success at this job, before deciding to bolt to Las Vegas. Here, Walters partnered with the “Computer Team” to dominate the sports betting world.

They were named the Computer Team because they were among the rare gamblers using PCs in the 1980s. Their early knowledge of computers paid off, as they were able to calculate advanced metrics.

Super Bowl 44, New Orleans Saints, Indianapolis Colts

Walters continued winning big bets long after bookmakers caught up to the Computer Team’s ways. His crowning achievement is when he won $3.5 million on Super Bowl 44.

He had a good feeling about the New Orleans Saints toppling the favored Indianapolis Colts. His intuition paid off when the Saints won 31-17.

Walters admits that he used bad bankroll management in this case. But few can argue with the result. Unfortunately, Billy was convicted in an insider-trading scandal involving Dean Foods. He’s now serving a stint in federal prison.

Gerry McIlroy

Rory McIlroy is one of the most successful golfers of all time. He has four Major titles and 14 overall PGA tournament wins.

It appears that McIlroy was always destined to be a success. However, this wasn’t entirely the case when he was growing up in Northern Ireland.

Nevertheless, his father, Gerry, placed a bet on his teenage son winning the British Open within 10 years. The proud dad bet £200 at 500 to 1 odds that Rory would soon be a British Open champ.

Rory was 15 when the bet was made and went on to win the Open at age 24. His father pocketed £100,000 as a result.

50 Cent

Curtis Jackson (a.k.a. 50 Cent) is a New York native who loves the Giants. That said, he was looking to bet big when the G-Men made Super Bowl 46.

50 first caught betting hysteria when New York played the San Francisco 49ers in the 2011 NFC Championship. He won a $500,000 wager when the Giants pulled out a 20-17 overtime victory.

New England Patriots on Field

Next up was an even tougher task, the undefeated New England Patriots. Jackson bet $1 million on the underdog Giants and was successful again when they won 21-17.

An interesting side story here is that fellow rapper Birdman wanted to bet $5 million against Jackson. 50 declined the $5 million amount, but was willing to wager $1 million against Birdman.

The latter thought the stakes were too low and turned Jackson down. However, 50 did find a sportsbook that took the bet.

Mick Gibbs

Mick Gibbs was just a simple roofer from Staffordshire, UK, when he decided to make a life-changing bet. He wagered 30 pence on a 15-team soccer accumulator.

The odds of him winning were just 1.67 million to 1. He was on his way to defying the odds, though, when the first 14 teams won.

The final game involved Bayern Munich and Valencia. Gibbs had Bayern winning this Champions League final.

The match provided extra suspense by going to penalty kicks. Bayern Munich emerged victorious, giving Gibbs a £500,000 payout on his tiny original bet.

Fred Craggs

Fred Craggs is similar to Mick Gibbs in that he was just a simple man before sports betting changed his life. The fertilizer salesman decided to make an eight-horse parlay wager on his 60th birthday.

He risked 50 pence on the bet and didn’t take much time looking over the selections. His odds of winning were 2 million to 1.

Horse Racing

Craggs walked into a William Hill betting shop later on to make more bets. He didn’t realize, though, that his parlay had been successful.

He should’ve actually won £1.4 million on the wager. But William Hill’s terms capped his parlay win at £1 million.

Regardless, he was still extremely happy about the win. Craggs was able to retire earlier than expected afterward.


You can see that people from all walks of life are capable of winning big in sports gambling. Some are skilled pros who develop a great strategy, while others are amateurs who’ve defied the odds.

Drake’s dad is the latest remarkable story from the sports betting world. He risked quite a bit ($100k) on the Raptors winning, but was well rewarded with a $300,000 payout.

Sir Ride A Lot brings another impressive tale. He let his winnings ride on six straight World Series games, earning a combined $14 million as a result.

Haralabos Voulgaris and Billy Walters both relied on strategy rather than luck to win big. Both have made millions from sports gambling over their careers.

50 Cent, Gerry McIlroy, Fred Craggs, and Mick Gibbs are a few more cases of being lucky, rather than great bettors. Nevertheless, they all profited big from sports wagering as well.