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The Good Life

How to Bet on Sports

Don’t place your bets on the big (or small) game without our expert’s guidance
| By Danny Sheridan | From Matthew McConaughey, July/August 2018
How to Bet on Sports
Illustration/Max-O-Matic

Since May 14, 2018 when the Supreme Court legalized sports betting in any state that wants it, several dozen states have been scrambling to get in on the action. And the potential amount of that action is considerable: I estimate more than $200 billion is bet illegally each year on sports in the United States. “The Supreme Court’s decision is a victory for millions of Americans who want to bet on sports in a safe and regulated manner,” says Geoff Freeman, president and CEO of the American Gaming Association. “Before this ruling, the government was turning tens of millions of Americans into criminals for the simple act of enjoying [betting] on sports.”

So will this new law put illegal U.S. and offshore bookies out of business? No, because bettors accustomed to betting with them don’t want their wins or losses disclosed to the IRS or newspapers. But this new law is certain to drive millions of Americans to embrace sports betting. Those who bet already are likely to bet more, and the law change means new bettors will enter the sports betting world.

While it’s undeniably a new day for sports betting, it’s important to tackle this land of opportunity with solid advice. There are smart sports bets and there are sports bets to avoid, and I have proven strategies to help guide you. Here are my suggestions on how to intelligently bet on college and pro football, Major League Baseball, the NBA and college basketball.

Baseball: Play The Streaks Early

If a baseball team wins three games in a row, you need to bet on them until they lose. Conversely, if a team loses three in a row, bet against them until they win. I call this the Streak Theory, and it does very well in April and May. I’d recommend not using it after May 31st, as oddsmakers sharpen their lines after the first two months of the Major League Baseball season. Just this year alone, there were several long (and profitable) streaks. The New York Yankees went on a nine-game winning streak in late April, and an eight-game streak in early May. The Mets and Boston each won nine in a row in April, while Tampa Bay and Milwaukee had 8-0 runs. In April and May, Kansas City lost nine in a row, and Cincinnati, Minnesota and Tampa Bay all notched eight-game losing streaks. Streaks can put money in your pocket.

But don’t bet baseball every day. It’s guaranteed to be very hazardous to one’s wealth. The idea of the Streak Theory is to reduce your plays and to take advantage of unexpected early season streaks. 

The Three-Game Theory Of College Football

Most bettors make the mistake of using comparative scores when handicapping college football games, which lands them on the favorite, but that strategy will give you a loser 70 percent of the time against the spread. I do just the opposite, in what I call my Three-Game Theory. For example, because Alabama beat LSU, and LSU beat Auburn, most bettors incorrectly assumed that favored Alabama would rout underdog Auburn when they squared off in the Iron Bowl last November. In the matchup, Auburn (who I picked) upset Alabama 26-14. By the same token, Miss State beat LSU, LSU beat Ole Miss, so therefore many people picked 14-point home favorite Miss State to rout Ole Miss in their rival season-ending “Egg Bowl” match. But as my good friend Lee Corso says, “not so fast my friend.” Ole Miss won outright, 31-28.

So why bet against the favorite when they’ve beaten a team that has already beaten their upcoming opponent? The favorite team in that situation, knowing they’ve beaten a team that beat the team they’re playing, enters the game understandably very overconfident—which is the exact opposite feeling of Team C, the underdog. And that’s why I pick the underdog when this situation arises.

There are plenty of other examples of this theory paying off. Ohio State beat Penn State, Penn State beat Iowa, but Iowa upset Ohio State 55-24. Arizona beat UCLA, UCLA beat Arizona State, but Arizona State upset Arizona 42-30. FSU beat Wake Forest, Wake crushed Boston College but Boston College (a six-point underdog) demolished FSU 35-3. Convinced?

Pro Basketball: Ignore The Regular Season

There are just too many games in the regular NBA season (82) for a serious bettor to pay attention to, and that means it’s impossible for players to play every night to their mental and physical ability. It’s the same with the playoffs. Today’s NBA playoffs consist solely of seven-game series, which often produces clunkers against the spread. Don’t bet the NBA regular season or individual playoff games. Do bet early first- and second-round NBA playoff series small underdogs, but don’t bet on 5:1 or greater series underdogs, who usually lose to superior high-ranked teams. 

College Football: Distance Makes The Bet Grow Fonder

Put your money on the first six bowl underdogs that play on the opening Saturday (last year, that was December 16). Usually, those teams are the most motivated, and last year, they went 5-1 against the spread. Double up your bet if that 5-7 bowl team is playing far away from home. Nebraska, with its 5-7 record in 2015, upset 8-4 UCLA as a 5 ½-point dog, 37-29. The game was played in Santa Clara, California, about 1,600 miles away from Cornhusker country. San José State, a one-point favorite with a 5-7 record, beat Georgia State 27-16 in the 2015 AutoNation Cure Bowl. They were playing in Orlando, nearly 2,800 miles from home.

College Basketball: Watch The Rematch

In college basketball, conference foes play each other twice in the regular season. When a team beats the spread in the first meeting, bet against that team in the rematch. If the point spread loser of the first game also loses straight up and the first-game loser is a road underdog, double your bet in the rematch.

NFL Regular Season: Look To The Sequel

The same strategy for betting on regular season college basketball applies to division foes in the NFL regular season—bet against the team that beats the spread the first time they meet. 

Pass On Parlays

Never bet on basketball or football parlays. The odds of correctly picking a two-team parlay against the spread is 3:1 against you (with a bookie payout of 2.65:1). In a three-team parlay, those odds increase to 7:1 (payout is 5:1), and a four-team parlay leaves you with 15:1 odds against you (the payout is only 10:1). Need I say more?

Bet Early, Bet Late

Finally, bet a favorite early in the week. Betting the underdog? Save your bet for as late as possible on game day. Why? The public loves to bet on favorites, so it’s best to place favorite bets the minute the line is released. Favorites, more often than not, are bet up during the week, so a team that opens as a 5 ½-point favorite will move a point or two (or more) higher by game time. Conversely, if you like the underdog, wait right until game time or the day of the game, as you’ll get the most value on them as the line moves in your favor. That’s how you get the best value on a favorite or underdog. 

Cigar Aficionado contributor Danny Sheridan appears frequently in major newspapers and on major TV networks. 

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