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Mayweather vs. McGregor: Expert pick and analysis from veteran handicapper

The 'Money Fight' offers numerous ways for bettors to take action. SportsLine analyst Josh Nagel breaks down the bout and offers his top selections on proposition wagers.
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What: Floyd Mayweather vs. Conor McGregor

When: Saturday, Aug. 26, 9 p.m. ET

Where: T-Mobile Arena, Las Vegas

TV: Showtime Pay-Per-View

Odds: Mayweather -550, McGregor +425

Odds courtesy of William Hill US

There's a high level of betting interest in the avant-garde, cross-sport clash between cartoonish combat sport antiheroes Floyd Mayweather and Conor McGregor.

Unofficially dubbed "The Money Fight," both combatants stand to earn a nine-figure payday for their participation in a 12-round boxing match Aug. 26 at the T-Mobile Arena in Las Vegas.

Lured out of a two-year retirement by the mesmerizing sight of mountainous cash piles, the 40-year-old Mayweather puts his legacy and undefeated boxing record on the line. He is a five-division world champ with a record of 49-0, 26 knockouts. His last bout was a lopsided win over Andre Berto in October 2015.

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The flamboyant McGregor rapidly rose to UFC fame in part because of a well-crafted storyline that promoted him as a transcendent mixed-martial arts talent fueled by an outwardly arrogant and ambitious facade.

But the Irishman held up his end of the deal as the fights grew increasingly more difficult, becoming a two-division UFC champion with a submission loss to Nate Diaz the sole setback on his resume since joining the promotion. The 28-year-old's MMA record is 21-3 with 18 stoppages.

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McGregor is noted for his immense power, particularly in relation to his size, while Mayweather's boxing legacy is largely defined as maestro of the sweet science whose specialty is avoiding conflict.

What began as some verbal jostliing through the media ultimatetly resulted in this unlikely matchup becoming a reality, with McGregor making his professional boxing debut and Mayweather looking to end his career with an unblemished 50-0 ledger.

Long before the contracts were signed, many sportsbooks offered live odds on the potential bout, with Mayweather listed as high as a -2,500 favorite at some outlets.

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When the fight was officially made, sentiment quickly and heavily favored the underdog McGregor, with much of the public apparently sold on his self-belief system and the power of his left hook.

This sentiment gained even more momentum this week after the fighters agreed to use eight-ounce gloves for the bout. The lighter gloves are seen as an advantage to McGregor, who is widely viewed as the more powerful puncher.

This changed caused William Hill US to move its price on Mayweather from -600 to -550, with McGregor fetching +425.

In a news release, William US lead oddsmaker Nick Bogdanovich said the Nevada-based sportsbook has a multimillion liability on McGregor, and the prospect of the Irishman winning, "would be our worst sports result ever."

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"We are hoping that McGregor's two-round knockout prediction with the smaller gloves doesn’t ring true," he said.

Of the many propostiion wagers available for this bout, here are the ones I'm recommending:

Proposition: Over/Under 8.5 rounds. Pick: Under (-130). Both the price and number of rounds are a key factor in making this wager. Some outlets opened as high as 9.5 rounds, and many have since dropped as low as 7.5. Getting the Under 8.5 for this price is a fair deal on both fronts.

The most probable outcomes fall under this umbrella. Of course, few observers see McGregor capable of winning a decision, so any scenario in which he wins likely sends this Under.

Mayweather peppering and stopping a gassed-out McGregor in the middle rounds also is a viable outcome. Moreover, the fight ending on any sort of foul or cut is likely to happen the earlier rounds, when the most action is likely to take place.

Proposition: Over/Under 6.5 rounds. Pick: Under (+170). The price has dropped from an opener of +250, but it’s still a pretty solid overlay for this prop. Again, whatever action this fight offers should take place in the early rounds and, although a snoozer that goes the distance is always possible in a Mayweather fight, an early end has a much higher chance in this bout.

Proposition: Manner of Outcome. Pick: Mayweather by stoppage (-135). One thing that can’t be disputed about Mayweather is that he always knows his opponent. Many of his later-career fights were justifiably criticized for lacking action because Mayweather made it a priority to stay out of harm’s way. He respected the power of world-class opponents such as Canelo Alvarez, Manny Pacquiao and Marcos Maidana and mustered just enough offense to win rounds.

It should be a different story against a boxing novice such as McGregor. Mayweather will likely find openings in which he can land combinations, instead of the one-shot approach he often uses against bigger punchers.

Mayweather's power is better than most observers believe, and he could wear down McGregor over the course of the fight with a sustained attack. Also, the Irishman's stamina has been an issue in his longer UFC bouts and, although he's surely stepped up his endurance training, it’s difficult to envision this going the full 12 rounds.

Whereas Mayweather by decision (+200) has long been the safest bet in the boxing champ's bouts, this one should reverse course with a stoppage. 

Josh NagelSenior Analyst