Follow The Money | May 5, 2026 | Hour 2
Get the full intelligence
Search transcripts, export clips, track mentions, and explore all topics from “Follow The Money | May 5, 2026 | Hour 2” inside PodZeus.
In this second hour of 'Follow the Money' on VSiN Best Bets, hosts Mitch Moss and Pauly Howard dive deep into the NHL and MLB betting landscape, starting with the controversial hiring of John Chayka as the Toronto Maple Leafs' new GM. The episode unpacks the viral backlash from reporter Steve Simmons, who labeled Chayka a 'con man' and 'scammer' due to his lack of recent NHL experience and troubled tenure with the Arizona Coyotes. The hosts debate the NHL's 'old boys club' culture, especially in coaching and front-office hires, while analyzing the high-stakes NHL draft lottery, where the Leafs must secure a top-five pick to avoid sending it to Boston. The conversation shifts to MLB, where the hosts highlight undervalued teams like the Kansas City Royals, Toronto Blue Jays, and Tampa Bay Rays, all trading on recent underdog success and strong underlying stats. They advocate for 'buy low' plays on teams like the Orioles and Yankees, while cautioning against overvaluing favorites like the Mets and Dodgers. The episode closes with a showcase of high-risk, high-reward parlays—featuring long shots like the Twins winning the fewest games, Timberwolves winning the NBA title, and Murakami leading the league in home runs—emphasizing the power of contrarian thinking and strategic risk-taking in sports betting.
The NHL's front-office hiring process is often driven by connections, not merit—highlighted by the controversial Chayka appointment.
Teams like the Blue Jays and Royals are undervalued 'buy low' opportunities despite poor records, based on strong underlying stats and roster potential.
The draft lottery is a high-stakes game for the Leafs—securing a top-five pick is critical to avoid losing it to Boston.
Tampa Bay's pitching staff, led by Rasmussen, is a hidden gem with a 1.18 ERA over their last 11 games.
Long-shot parlays—like the Twins winning the fewest games or Murakami leading in HRs—can deliver massive payouts if you're willing to take calculated risks.
…and 3 more takeaways available in PodZeus
The Chayka Controversy & NHL's Old Boys Club
“I talked to 19 of 20 people, and they said scammer, con man, fake. This is your guy.”
Draft Lottery Drama & Leafs' Survival Strategy
The hosts analyze the NHL draft lottery, emphasizing the Leafs' desperate need to secure a top-five pick to avoid sending it to Boston. With a 41.9% chance of failing to secure a top-five pick, the stakes are high. The discussion also touches on the broader Canadian hockey identity and the emotional weight of Montreal's dominance.
MLB's 'Buy Low' Playbook: Royals, Blue Jays & Rays
“They're only a game and a half out. And now they've won eight of ten. Yes.”
The Power of Long-Shot Parlays & Contrarian Bets
“If you're not ending every one of these cross-sport parlays with Dodgers to win the World Series, I just think you're doing it wrong.”
Tampa Bay's Hidden Pitching Power & Rasmussen's Edge
“Their starters are ERA in that stretch is 1.18. They've allowed three runs or fewer in all of Levin.”
“I talked to 19 of 20 people, and they said scammer, con man, fake. This is your guy.”
“If you're not ending every one of these cross-sport parlays with Dodgers to win the World Series, I just think you're doing it wrong.”
“Their starters are ERA in that stretch is 1.18. They've allowed three runs or fewer in all of Levin.”
Hosts
Guest
Pauly Howard
person
Mitch Moss
person
Toronto Maple Leafs
other
Tampa Bay Rays
other
Toronto Blue Jays
other
Los Angeles Dodgers
other
Kansas City Royals
other
John Chayka
person
Nick Alberga
person
Baltimore Orioles
other
VSiN By The Books | March 31, 2026 | Hour 1
VSiN Best Bets • 45m • 3/31/2026
VSiN By The Books | March 31, 2026 | Hour 2
VSiN Best Bets • 45m • 3/31/2026
VSiN By The Books | March 31, 2026 | Hour 3
VSiN Best Bets • 45m • 3/31/2026
A Numbers Game | March 31, 2026 | Hour 1
VSiN Best Bets • 45m • 3/31/2026
A Numbers Game | March 31, 2026 | Hour 2
VSiN Best Bets • 45m • 3/31/2026
Get the full intelligence
Search transcripts, export clips, track mentions, and explore all topics from “Follow The Money | May 5, 2026 | Hour 2” inside PodZeus.
Start discovering podcast insights today
Start with a 7-day trial and explore a growing catalog of popular podcasts. No credit card required.
No credit card required • 7-day trial • Cancel anytime