The Best Sports Gambling Tales: $200,000 Won in 3 Months: How Monty Is Turning The Parlay Pro

🚨 ATTENTION NEW YORK 🚨 THIS OFFER EXPIRES AT 11PM (ET) TONIGHT

Read more about this Dimers x Caesars Exclusive New York offer here!

---

The old school gamblers refer to it as simply the ‘P word’. It’s a word so dirty among the established generation of sharps that they can’t even bring themselves to say it out loud, let alone actually make one. But just like how Steph Curry’s three-ball completely changed the NBA, one man and a new breed of gamblers are blowing up the establishment with one simple bet that they’re hitting over and over again.

We’re talking about parlays. And they’re on the brink of going pro.

This article is brought to you by BetMGM Sportsbook.

New customers with BetMGM Sportsbook can claim $200 in free bets when there's a 3-pointer in ANY NBA game. All you need to do is place a $10 Moneyline bet on ANY NBA team and you'll score $200 as soon as someone hits a triple.

Blair Montgomery, from Illinois, claimed notoriety and instant online fame earlier this NFL season when he went on an insane run, hitting multiple long shot parlays from Weeks 3-5 to walk away with more than $125,000. However - contrary to what those sharps will tell you - it’s no fluke that Montgomery continues to win. 

The 31-year-old was introduced to gambling when he was just 15-years-old during the poker boom of the 2000s when guys like Daniel Negreanu and Phil Ivey were gods. Speaking to Dimers.com, the poker fan tried to make a living by playing cards before eventually finding his way into the world of sports betting.

“I traveled the midwest quite a bit through my early-to-mid 20s in hopes of going pro and doing it full time, but I just never could get that one big score that gave me the bankroll to quit my job,” he said. 

“It was a great side hustle for me and I learned a lot of good (and tough) life lessons through Poker. 

“I got into sports betting once it became legal in Indiana, Illinois and Michigan over the last few years. 

Blair, who currently works in software sales, saw his life change in an instant during Week 3 of the 2021 NFL season when he used his usual Sunday parlay strategy to good effect, finding himself in a position to win over $40,000 on Monday Night Football.

Recounting the events of the monster win which took place while he was in attendance at a friend’s wedding in Detroit, Montgomery says things got a little intense.

“On the drive down [to the wedding] I hammered out my usual strategy, which is roughly 10-12 parlays of differing variations for NFL Sunday,” he explained.

“I had a 12-leg moneyline parlay at odds of +42754 on a $100 bet that was really gaining steam through the 1pm kickoffs. 

“I didn't really predict anything crazy - I had a few +125 upsets thrown in there (Falcons, Saints, Bengals) but I also had the Ravens over the Lions.”

That game, where the Ravens closed as -380 favorites, was anything but as easy as those odds suggested, with a Justin Tucker 66-yard field goal required as time expired to give Blair another green tick on his betslip.

As the wedding ceremony went on, more legs cashed. But as the festivities turned to the speeches, there was more drama - the Dolphins and Raiders just went to OT, and he needed Vegas to pull through.

“At this point, all of my friends around me were well aware that I had $40k on the line and needed the Raiders to win,” he recalls.

“The Dolphins converted two absurd 4th downs to extend the game and I damn near had a heart attack during the Father of the Bride's speech.

“Thankfully, the Raiders pulled it out and I was down to the last leg (Cowboys ML)”.

The standalone match on Monday Night Football between the Eagles and Cowboys allowed the savvy bettor a chance to hedge his bets to guarantee a win no matter what, by putting down $20,000 on the Eagles at the +3.5 spread.

“It turned out to be a bad decision because the Cowboys smoked Philly but I still netted $23,000” he said.

Hey @dallascowboys…what’s good?👀👀👀@FDSportsbook @ActionNetworkHQ pic.twitter.com/uIJ9tgP4WU

— Blair Montgomery (@MontyParlay) September 27, 2021

While the ultimately unsuccessful hedge didn’t pay off in Week 3, a lightbulb went off for Montgomery that night, leading to the Week 4 strategy he devised that he simply refers to as ‘The MNF Pre-Hedge’.

“I wanted to get to a point where I was trying to take hedging out of it and I was guaranteeing myself more money,” he told us.

“I fire off a lot of these parlays as it is, so I thought why not just take the last leg out of it and take the moneyline for each team. 

“A lot of people are like, "Well why would you even bet the last leg then?!?" and my thought process is because it makes that last leg mostly stress free. Getting to the point where you're free rolling for an extra $40,000 is the best feeling in the world.”

With two identical parlays in place for Sunday - the only difference being the moneyline winner of the Monday Night Football game between the Chargers and Raiders, the man known as Monty Parlay had everything go his way once more, getting to Sunday night needing only a Tom Brady win on his return to New England to guarantee at least an $80,000 win, or a maximum cash of $125,000, depending on the outcome of Monday night.

The result? Bucs 19. Pats 17.

“It was damn near the most stressful three-and-a-half hours of my life.”

The bag was secured for MNF, but, somewhat unfortunately, Blair only won the lesser parlay of $80,000 as the moneyline favorite Chargers trampled over the Raiders.

In Week 5, it happened again - getting to Monday’s game between the Ravens and Colts and collecting another $35,000 as Baltimore ran out winners.

In three consecutive weeks, Blair Montgomery had just cleared $125,000.

Since then, life has gotten crazy for the Illinois bettor. His Twitter account exploded to a base of over 14,000 followers and he has continued to keep the hot streak rolling on a weekly basis, hitting impossible parlays over and over with another $145,000 in winnings just in the first three weeks of January alone, including last night where he hit a +5400 Same Game Parlay between the Suns and Mavericks to walk away with another $55k.

LFG!!!!!

Garbage time lob from Brunson to KP to lock up $55k!!! Shoutout to my guy @DevinsBookie

That’s my 3rd SGP on a Suns Mavs game this year. 5th or 6th on a Suns game. Wow😈😈😈 https://t.co/6AVRv8vNi3 pic.twitter.com/5cb9aQpRE8

— Blair Montgomery (@MontyParlay) January 21, 2022

These are plays that most bettors dream of hitting just once in their lives, but Montgomery and others that we have featured in the past on Dimers.com such as Meezy, TheMisterMarcus and KiiLkenny, are proving that parlay betting can be not just sustainable, but profitable, to the point where these guys could live comfortably through their gambling wins, as well as other advantages of success in this industry, like VIP subscriptions from other bettors in the community hoping to ride the hot hands.

Speaking about how the paradigm has shifted towards the popularity of lotto-type parlays as sports gambling continues to breakaway from the streets of Vegas and into the mainstream, the en fuego gambler says a number of factors are contributing.

“There’s a generational gap [between old bettors and current day sports gamblers]. I got my first cell phone when I was 15,” he said.

“There’s a difference in technology. We have access to every sport on a regular basis, and with that, parlays become more sustainable because of the tools out there that those old guys didn’t have.

“The sportsbooks would always prefer you to bet parlays over straight bets because the odds are so much harder to hit, but at the end of the day, depending on the type of person you are and your understanding of sports, it’s possible to beat the game.”

Are you in New York? Sports betting is now legal in NY and Caesars Sportsbook have the best offer out there for new users. Claim a $300 free bet and a deposit match up to $3000 when you sign up!

Just like how the best pro athletes can make their jobs look easy, Montgomery says that this isn’t for everyone, and he has a very unique skill that leads to his consistent success.

“I’ve always been the person from my friend group who is the numbers guy and the sports guy,” he explains.

“I’ve always remembered random little plays, or draft picks, or where they went to school or who they were coached by and it helps me. 

“I watch sports religiously. I notice tendencies and I remember things - it just sticks with me.

Even though the crazy highs have been exhilarating over the past couple of months for Blair, he still realizes that it could all be gone in an instant, and is weary of how others watching his gigantic wins from afar could find themselves in trouble trying to replicate his methods.

“If someone is looking at this and wants to bet parlays and is dreaming of winning a $40k parlay; it sounds cliche, but it’s about bankroll management,” he warns.

“Until you get to a point where you can discipline yourself enough to the extent where you’re down 15 units and you’re not live betting stupidly to get back even, you’re not mentally strong enough to do it. You have to remain disciplined and realize the wins will come.”

For now, though, Monty continues to beggar belief with his run, and it’s changing absolutely everything that we once thought we knew about sports gambling.

Blair can be followed on Twitter @MontyParlay