Adam Matmon was nearly ready to throw in the towel on his 4-leg, $390 parlay last Monday.

The Tigers were down three runs to the Braves – in the ninth. The Rockies trailed the Red Sox. The Angels were getting drubbed by Texas. Even if all three rallied to win, Matmon still needed the worst team in baseball (the A’s) to topple the team with the best record (the Rays).

“To give you an idea of how much of a longshot bet that was, at one point the cash-out option was like $12,” said Matmon. “Sometimes the ball has to bounce your way.”

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The 38-year-old Matmon lives in Hoboken, N.J., and works in real estate private equity. When the U.S. Supreme Court repealed PASPA in 2018 and New Jersey legalized sports betting, Matmon tried out a few different apps. PointsBet emerged as his choice.

“I thought PointsBet’s interface was way easier than the others,” Matmon said. “I got connected with [loyalty manager] Seth [Ampolsky] pretty early on because I hit a few big bets, and I’ve kept using PointsBet ever since.”

While he also gambles on football and college basketball, Matmon’s bread and butter is baseball. Although he’s a diehard Yankees fan, he rarely includes them in his parlays. He prefers moneyline underdogs.

“When most people do baseball parlays, they probably go with the favorites,” Matmon said. “But I think that’s doing it wrong. Baseball is less predictive than the other sports. The top teams lose 60-65 games a year, so the winning percentage is about 60%. For football and basketball, it’s closer to 75%. So I think right away, you have a little bit of an edge if you attack baseball parlays that way.”

Prior to last week, Matmon had already hit on three different parlays this baseball season at PointsBet. On March 30, he put $400 on White Sox ML +120, Rockies ML +185, Athletics ML +175 and a rare NBA leg of Celtics ML +110. That paid out $14,483.70. On April 13, he turned $350 into $13,928.54 with Reds ML -145, Tigers ML +220, Pirates ML +220 and Brewers ML +130.

The biggest longshot parlay that Matmon cashed this season came on May 16 with this $88, 7-legger: Rangers ML -115, White Sox ML -110, Reds ML +115, Royals ML +165, Athletics ML +130, Giants ML -110 and Twins ML +165. That added $23,292.71 to Matmon’s pocket.

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That brings us to last Monday, when Matmon scoured over the 8-game slate. He put $390 on a parlay featuring the four biggest underdogs on the board: Tigers ML +210, Rockies ML +190, Angels ML +130 and Athletics ML +220.

Matmon has the MLB TV package, and he watches most of the games he bets on. Sometimes he’ll be with friends, but that Monday he sweated out his action alone. The Tigers were down 5-2 in the bottom of the ninth (and 5-1 in the eighth) to the Braves, and they seemed destined to lose their 10th straight game. But Spencer Torkelson came through with a two-run homer in the ninth and a walk-off single in the 10th.

“This is huge,” Torkelson said after the game. For him and Matmon.

The Angels also trailed by four runs to the Rangers but squeaked out a 9-6 victory in 12 innings. The Rockies also needed extras to triumph at Fenway. That left the Athletics, who raced out to a 4-0 lead over the Rays and held on, 4-3.

“All these comebacks were happening all at once,” Matmon said. “After the A’s won, I texted a few buddies with ‘Can you believe it?’ I was shocked because usually you can tell early on if you have a shot, but I needed two big comebacks.”

How did Matmon celebrate his $25,804.90 win? He put most of it away in the bank, but then he threw down $1,260 on the same four teams for a parlay the next day: Tigers ML +220, Rockies ML +185, Angels ML +120 and Athletics ML +175.

While Braves at Tigers was rained out, the other three squads came through again. The Rockies once again pulled off a 10th-inning win over the Red Sox, 7-6. The Athletics edged the Rays 2-1 with the go-ahead run being plated in the eighth.

The Angels were the easiest leg, though three of the runs in their 7-3 victory came in the ninth. That was the only leg either day that wasn’t either a 1-run or an extra inning win. With the Tigers leg voided, last Tuesday’s parlay payout paid $23,456.66.

“That was the best two-day stretch I’ve had,” Matmon said. “It’s also my best baseball betting season. When you bet this kind way with a bunch of underdogs in a parlay, you have to get used to losing a good amount in a row. The fact that I got two of these back-to-back, it was pretty wild.”

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