Pirates Can Be Exhibit A For How To Come Out Ahead Betting Baseball Underdogs

No, the Pittsburgh Pirates aren't a good team, but they didn't have to be to win money betting on them in April as underdogs.

There is a theory that shrewdly betting moneyline underdogs over the course of a long baseball season is one strategy to beat the sportsbooks’ house edge.

The theory does not include any particular recommendation to bet every game on the Pittsburgh Pirates — widely deemed the worst MLB team before the season started — but their April performance is a showcase for how the strategy can succeed.

The Pirates, with their unheralded lineup and duct-taped pitching staff, started the season 1-6, as though wanting to prove every forecast for their ineptitude to be inaccurate — but only for underestimating just how truly pathetic they would be. But they rebounded to finish 12-13 in April. That .480 winning percentage came with the Pirates a favorite in only one game and a plus-price underdog in all but two. In games in which they were a huge underdog of +150 or more, they actually went 6-4.

Our rough, seat-of-the-pants calculations from odds checked at DraftKings once a day (the odds can vary throughout the day, obviously, and we weren’t constantly updating) showed that if a recreational bettor risked $10 on the Pirates 25 times in April, he would have come out about $47 ahead overall.

That’s not enough in the increasingly relaxed restaurant world to take a family out to a good steakhouse, obviously, but for the satisfaction of being a winning bettor and maybe taking a date to Applebee’s? Yeah, that would be doable, so long as you don’t get carried away there with margaritas or desserts. (We would use the example of betting $100 per game and coming out $470 ahead if we were writing for professional gamblers, but we doubt they’re relying on us for assistance.)

Listen to VSiN if not us

In an article published in the New York Post April 1, Josh Applebaum of VSiN summed up the strategy behind betting moneyline underdogs thusly:

“One advantage in baseball is that if you avoid big favorites and focus on underdogs, you can win at a sub-50 percent clip and still turn a profit based on the plus-money payouts (think +110, +130 or +175).

“However, this doesn’t mean you should bet every ‘dog. The key is focusing on divisional ‘dogs. They perform much better than underdogs playing out of their division. This is due to built-in familiarity.”

Indeed, underdogs have done well this year, as one estimate has shown them winning at a 47.5% clip. We haven’t seen a divisional breakdown for such bets overall. Ironically, betting the Pirates in divisional games in April is one way in which a bettor would have taken a slight loss, as they went only 5-8 against the Cubs, Reds, Brewers, and Cardinals. But by about any other calculus — whether home games, road games, etc. — the Pirates would have generated a profit for their consistent backers.

The trend started in season’s opener at +180

With sportsbooks on average having an -110 edge in how odds are set, a bettor typically needs to win 52.4% of the time to come out even slightly ahead. The necessary winning percentage, however, is well below that when betting baseball underdogs, and the strategy behind betting them is that even bad teams typically win at least 40% of the time.

From their very first game of the season, at Chicago on April 1, the Pirates demonstrated how bettors could take advantage of the low expectations for them. They were +180 in that opener vs. the Cubs’ Kyle Hendricks, and they won, 5-3. Their other wins as big underdogs:

  • April 13: They were +215 as home underdogs against the San Diego Padres, and they knocked Padres starter Blake Snell out in the first inning of an 8-4 win.
  • April 14: The next night they were +180 against the Padres’ Joe Musgrove, whom had been traded away by the Pirates as part of their rebuilding effort, and they beat him, 5-1.
  • April 18: Visiting Milwaukee, the Pirates were +175 and won, 6-5.
  • April 24: Again a big road ‘dog at +175, the Pirates beat the Minnesota Twins, 6-2.
  • April 25: The Pirates beat the Twins by the same score the next night as a +170 underdog.

This all comes with caveats, but …

To be sure, this is all small sample size stuff, regarding one not-good team’s performance in one month. And there is a theory that April in particular is a good time to bet underdogs, as there are a lot of uncertainties about teams being either stronger or weaker than anticipated and every team still feels in the running for a postseason berth.

As evidence of early season oddities, no team in the NL East currently has a winning record and the San Francisco Giants lead the Los Angeles Dodgers and the Padres in the NL West. No one is counting on those scenarios to continue through September.

In the Pirates’ case, the common over/under on their wins total before the season started was a lowly 58.5, at least six games below the teams considered the next worst — the Colorado Rockies and Baltimore Orioles. Even after losing the first two games in May to fall to 12-15, the Bucs still need to go just 47-88 the rest of the year (.348) to make winners of those brave souls who were willing to bet the over on them more than a month ago.

There is nothing to be written here suggesting the Pirates are a good team, or even a decent team. Their run differential of -26 is better than only that of the Detroit Tigers, who are 8-21, implying a certain amount of luck has been involved in having a record as un-awful as it is and better than six other teams. They are near the bottom of nearly every hitting category, as expected, but a bullpen ranked third in the MLB in ERA and WHIP has done a good job of preserving leads when the Pirates have managed them.

So this is by no means a recommendation that a bettor risk $10 (or gasp, $100) betting on the Pirates in each of their 135 remaining games. It’s to serve as an example of how — in baseball in particular — riding a bad team that exceeds expectations can be one way to derive betting profits.

Just for the record, DraftKings on Monday morning had the Pirates listed +155 for their night game after traveling across the country to San Diego. Someone who had been willing to bet $1,000 per game on the Pirates when they hosted the Padres last month (some rich oddball might have done it, after all) would have come out about $3,000 ahead when Pittsburgh won two out of three.

Then again, there’s a theory to avoid underdogs when they’re struggling with losing streaks of three or more, and the Pirates have dropped four straight after climbing above .500. As always with sports betting strategies, things get complicated.

Sooo … maybe if you want to use this game to start your own moneyline underdog strategy, $10 instead of $100 or $1,000 might be the right way to go. Just sayin’.


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