Do sportsbooks from Atlantic City to Las Vegas have a proposition for you? Why yes, they do. Hundreds of them, in fact.
From a simple heads or tails, to the time of a headliner’s anthem to who’s headed to the endzone first, the world of the proposition bet, or “prop bet” for short is a whimsical, almost dizzying space where sporting events are broken down into varying degrees of categories with the potential for a winning – and losing – outcome.
For the casual bettor or the most serious of sharps, prop bets are an endless source of interest and opportunity.
But what exactly is a prop bet, and how do you navigate the difference between pure luck speculation and measured analysis? Well, if you bet that this introductory section would be less than 150 words, you’re already a winner. Let’s take a closer look at prop betting.
Prop betting became popular in the betting culture in January 1986, when Caesars Palace took advantage of the phenomenon known as “The Fridge.” The mighty Chicago Bears had just steamrolled through the NFC to reach Super Bowl XX against the Patriots. As expected, the Super Bowl itself was no contest, as the heavily favored Bears demolished the Cinderella Pats 46-10.
But because of the national sensation that were the Bears, from Jim McMahon to Buddy and Ditka to the Super Bowl Shuffle, Caesars decided to add a little spice to its betting menu for the big game.
Defensive lineman William Perry might have been the biggest Bears player of them all, literally and figuratively. Nicknamed “The Refrigerator” because of his enormous girth, Perry had broken all football convention during the regular season as coach Mike Ditka employed him as a goal-line back. And the Fridge did not disappoint, scoring touchdowns on the ground and through the air in goal-line sets.
So for a prop bet, Caesers set a line at 20-to-1 that Perry would score a touchdown in the Super Bowl.
And sure enough, much to the chagrin of Walter Payton and the Palace bookmakers, Perry scored a touchdown late in the rout.
Caesars Palace lost over $100,000 on the bet. But, really, everyone was a winner, as the famous Perry prop unleashed the modern era of the prop bet.

Unlike an actual bet on the outcome of an event, like the Super Bowl, with its point spread and over/under and moneyline, the proposition bet offers odds on a particular aspect of the game, both on-field and off. In almost all cases, the actual outcome of the game plays no part in factoring into a prop bet. Indeed, what makes prop bets so popular, especially for big-ticket events like the Super Bowl or the NBA Finals, is that you don’t really need to be a hardcore gambler or sports fan to make a wager and enjoy rooting for your winning outcome.
I offer from my own personal experience a typical big game prop bet:

In October 2018, I was enjoying a weekend in Las Vegas, and while watching my beloved Boston Red Sox rally to win Game 4 of the World Series from the sportsbook at the MGM Grand, I spied on the big board a prop bet already available for Sunday’s Game 5.

Which Player Will Score The First Run in Game 5

Regardless of which team would win Game 5 and how many total runs would score, Vegas understood that eventually at some point in the game – even if it lasted 18 innings like Game 3 — somebody would have to touch home plate first.
With that reality implied, the sportsbook offered odds on each player expected to be in the starting lineup for each team and assessed, largely through anticipated spot in the order and left- or right-handedness against the two probable lefty starting pitchers, which players were most likely to score that first run.
My eyes were drawn to Red Sox first baseman Steve Pearce, who was heating up as the series wore on and would be the kind of power righty bat who might launch one off lefty Clayton Kershaw. At 20-to-1, I liked the chances of Pearce slotting third in the batting order, garnering a guaranteed first-inning at-bat, and popping a solo shot to left to score the first run. I made my wager.
Sure enough, the next night, first inning of Game 5, Pearce batted third and blasted a Kershaw offering into the seats for a home run. My prediction was right on the money.
But I lost the bet.
Unfortunately, my analysis did not call for left-handed batting Andrew Benintendi to hit a one-out single just before Pearce stepped to the plate. So, as Pearce trotted around the bases with my called home run, Benintendi strolled in ahead of him, touching home plate for the first run of a 2-0 Red Sox lead.
Win some, lose some.

But such is the nature of the prop bet. An event, or outcome that occurs within the game becomes the fodder for the wager. Other such offerings for the Game 5 was over-under on how many pitches the starters would throw, which player would have the most RBI or the over-under on the length of the National Anthem.
But no sport and no event like the NFL and its Super Bowl is more prop friendly in the betting world.
Think of all the statistical measurements and milestones that go into an individual NFL game, and then imagine all the possibilities for prop bets.
Consider the Super Bowl between the Patriots and Rams. Here was just a sampling of the prop bets available to the public:

New England Patriots -132
Los Angeles Rams +100

Yes +109
No -144

YES -220
NO +172

YES -211
NO +167

YES -400
NO +292

YES -490
NO +345

New England Patriots -130
Los Angeles Rams +100

Over 7.5 +100
Under 7.5 -125

As you can see, the sportsbook balances its odds of a “win” or a “loss” not with the object of the wager, but with the moneyline. By skewing the moneylines on each side of the wager, the book is trying to entice the bettor to wager on the least likely of what are, essentially, a set of exotic over-under scenarios.
In the examples above, team achievements are at the heart of the prop. But the more popular prop bets are attached to individual performances. How many points, how many touchdowns, how many yards. Those questions lay at the heart of most prop bets. In Super Bowl LIII, these were prop bets available just for Tom Brady:

Total Pass Attempts: 37.5
Over: -110
Under: -110

Total Completions: 25.5
Over: -110
Under: -110

Total Passing Yards: 282.5
Over: -110
Under: -110

Total Rushing Yards: 1.5
Over: +130
Under: -150

Total Pass TDs: 2
Over: -110
Under: -110

Now imagine a similar string of bets for ever key skill player in the game. Even defensive players get in the act, with props on sacks, fumble recoveries and interceptions.
And if you were feeling frisky before Super Bowl XLVIII between Seattle and Denver, and bet the following prop: “The First Score Will Be A Safety” at 60-1 …
And then there are the prop bets for everything except the Big Game:

O/U on the length of the National Anthem
The color of Gatorade poured over the winning coach
First song played by the halftime performer
Number of Geico ads in the first half

And while many of these props are gimmicks that are often coin-flips, requiring almost no research or not qualifying for research (Coin toss: Heads or Tails), the actual player and team props can be properly diagnosed with a big of research and intuition.
If you analyzed Super Bowl LIII and determined based on matchups, tendencies and past performance that we were due for a major regression in points and yards from the two conference championship games, and you took the under on most of the Patriots and Rams’ props, you probably had a pretty good night for yourself.
Online sites such as 5Dimes, Bovada and Intertops are fine sources of prop bets for both major events and regular season games. And prop bets are not limited to football … as I discovered to my chagrin with Steve Pearce and Andrew Benintendi.