The History of Parlay Betting in Sports Gambling

Parlay betting has been a favorite option among sports gamblers for decades. I remember when bookies would hand out betting cards for college and pro football games, a true nod to the past. The excitement of turning a small bet into a bigger payout was unforgettable. But where did it all begin? This article explores its origins, evolution, and why parlay betting remains popular today.

What is a Parlay Wager

A parlay bet links multiple picks into a single wager, increasing both the risk and reward. To win, every selection in the bet must be correct – one wrong pick means the entire parlay loses. The main attraction of parlays is their potential for big payouts since the odds of each choice multiply, creating a much higher return than betting on each game separately. Players can mix different bet types, including moneylines, spreads, and totals, across multiple matchups or even within the same game. While the chance of winning decreases with each added selection, the thrill of a possible huge payout keeps many bettors coming back for more.

The Origins of Parlay Betting

The roots of parlay betting trace back to early bookmakers who sought to create high-risk, high-reward wagers for their customers. While no single person is credited with inventing the parlay, its earliest known use appeared in the United States during the early 20th century. Some historians suggest that Las Vegas sportsbooks were among the first to formalize parlays as an official betting option.

As legal sports betting expanded in the mid-1900s, prominent sportsbooks like the Stardust and Caesars Palace helped popularize parlays, making them a staple of modern gambling. Today, they remain one of the most exciting and widely available bet types across various sports and betting platforms.

Evolution of Parlay Betting

Parlays have come a long way since their inception. Originally, they were limited to major sports like football and horse racing. Today, however, sportsbooks offer parlays across multiple sports, from basketball to MMA. Modern technology has expanded options even further. Parlay wagers can now include player prop parlays, same-game parlays, and even live-betting parlays. This evolution keeps parlay betting fresh, exciting and very popular.

Why The Attraction to Parlay Betting

As I mentioned earlier, I used to enjoy those weekends with college friends betting with betting cards. It brought excitement to the weekend – watching sports on TV with friends in a dorm room, with some cash on the line. Even now, I enjoy partaking in a parlay wager from time to time. Many do.

Here are a few reasons why parlay wagers remain popular. First, they offer large payouts with a small investment. Second, they add excitement to multiple games at once. Lastly, they allow creative betting strategies. The chance to win big with a low wager makes parlays almost irresistible for many gamblers.

While I’m not a heavy parlay bettor (as I’ve mentioned before), we do include a parlay section in one of our courses – CSB’s Payoff Pitch. The reasoning behind that is simple – and, really, it happened by accident. While backtesting our usual payoff pitch method, we noticed that parlay wagering could be profitable when following the system.

If interested, here is a link to CSB’s Payoff Pitch.

Downsides of Parlay Betting

Now for the downside of parlay wagering (wah-wah).  Many handicappers advise against parlay betting due to its high risk and low long-term profitability. While the potential payouts are tempting, the odds are heavily stacked against the handicapper. Each additional selection in a parlay reduces the chance of winning exponentially, making it far less likely to cash in compared to single bets. Additionally, sportsbooks profit from the higher hold percentages on parlays, meaning they retain more money from losing parlay bets. Most professional bettors who focus on long-term success prefer straight bets, as they provide better control over risk management and a more sustainable path to profitability.

Quick Parlay Handicap Systems to Try

Now for the fun part of this article! If you’re looking to spice up your betting strategy, parlays can add an extra layer of excitement. While parlays are often viewed as long shots, the right approach can help you maximize value and improve your chances of success. Below, we’ll break down a few quick parlay handicap systems you can test out, giving you a structured way to approach these high-risk, high-reward betting opportunities.

Progressive Parlay

Description:

A progressive parlay allows for some flexibility in your bets. Unlike a traditional parlay, where all legs must win, some sportsbooks offer progressive parlays where you can miss one or two picks and still win a smaller payout.

How to Achieve It:

Select multiple games (usually between 4 and 12).

Choose a progressive parlay option if your sportsbook offers it.

Even if one or two legs lose, you can still win a portion of the bet.

Example:

You place an 8-leg progressive parlay on NFL games:

Kansas City Chiefs -6.5

Miami Dolphins -3.5

San Francisco 49ers -4.5

Dallas Cowboys -2.5

Buffalo Bills -5.5

Philadelphia Eagles -3.5

Detroit Lions -2.5

Baltimore Ravens -4.5

If six out of eight bets hit, you still win a reduced payout instead of losing everything.

Contrarian Parlay

Description:

This strategy goes against public betting trends by selecting bets where the majority of the public is on the opposite side. The goal is to take advantage of inflated odds due to heavy public action.

How to Achieve It:

Identify games where a large percentage (e.g., 70%+) of the public is betting on one side.

Bet on the opposite outcome, assuming odds are adjusted due to the heavy public money.

Combine multiple contrarian picks into a parlay.

Example:

If 80% of the public bets on the Lakers -5.5 vs. the Rockets, you bet:

Houston Rockets +5.5

Under 215.5 (if public is hammering the Over)

New York Knicks ML (if public is on the other side)

If the contrarian picks win, the odds are usually higher due to the public’s influence on the lines.

Cross-Sport Parlay

Description:

Instead of focusing on one sport, this strategy involves combining bets across different sports. This can help diversify risk and take advantage of value opportunities in multiple markets.

How to Achieve It:

Select games from different sports, such as NBA, NFL, MLB, and NHL.

Look for favorable matchups in each sport.

Combine moneyline, spread, or totals from different leagues.

Example:

Golden State Warriors -4.5 (NBA)

Tampa Bay Lightning ML (NHL)

Baltimore Ravens -3.5 (NFL)

Longshot Parlay (High-Risk, High-Reward)

Description:

A longshot parlay consists of multiple high-odds picks, often including big underdogs. While the probability of winning is low, the payout can be massive.

How to Achieve It:

Select multiple underdogs or high-payout prop bets.

Look for games where an upset is possible based on stats, injuries, or market inefficiencies.

Consider adding alternate spreads/totals for bigger odds.

Example:

Arizona Cardinals +7.5 vs. Kansas City Chiefs

Detroit Pistons ML vs. Boston Celtics

Under 220.5 in Lakers vs. Nuggets

A player prop: Travis Kelce anytime touchdown scorer

Since these are all riskier bets, the payout is significantly higher if all hit.

Favorites and Underdogs Mix

Description:

This strategy balances risk and reward by combining strong favorites with one or two underdogs that offer high value. The idea is that the favorites boost overall win probability, while the underdog increases the payout.

How to Achieve It:

Select one or two heavy favorites with a high likelihood of winning.

Add an underdog that has a realistic shot at an upset.

Consider matchups, injuries, and betting trends to find value underdogs.

Example:

Kansas City Chiefs ML (-250)

Milwaukee Bucks ML (-210)

Miami Heat ML (+180)

If the Marlins pull off an upset while the favorites win, the odds increase significantly compared to betting only favorites.

Two-Team, Low-Risk Parlay

Description:

This is a conservative strategy that focuses on maximizing win probability with just two well-researched picks. It’s a way to slightly boost earnings compared to single bets while minimizing risk.

How to Achieve It:

Find two teams with strong advantages (injuries, matchups, trends).

Use moneyline, spread, or totals to form a high-probability combination.

Avoid overcomplicating it with additional legs.

Example:

Philadelphia Eagles ML (-200)

Boston Celtics -4.5 vs. Chicago Bulls

This provides a modest odds boost while keeping win probability relatively high.

Over/Under Parlays

Description:

Instead of betting strictly on winners, this strategy focuses on totals (Over/Under) to find favorable matchups. Pairing moneyline bets with totals can create a strategic advantage.

How to Achieve It:

Identify games with clear scoring trends (high-scoring teams for Overs, strong defenses for Unders).

Combine Over/Under bets with moneyline picks or spreads.

Use historical data and team trends to make selections.

Example:

Over 225.5 in Lakers vs. Warriors

Under 42.5 in Steelers vs. Ravens

Dallas Mavericks ML (-180)

This mix lets you benefit from both team outcomes and game pace-based bets.

Conclusion

The history of parlay petting in sports gambling shows how it has grown into a staple of sports betting. It started with simple bets and now includes a wide range of options. Bettors love the excitement and potential rewards.

Maybe try out one of the above strategies, or experiment with your own, homegrown strategy. Make sure to backtest to some degree first. See if this is something that works for you.

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