Sharp or Square – MLB SEASON BETTING PREVIEW: Opening Day Best Bets, Futures & More

Podcast: Sharp or Square
Hosts: Chad Millman & Simon Hunter
Guest: Sean Zerillo
Date: March 24, 2026

Episode Overview

This episode kicks off MLB Opening Day week with Chad Millman and Simon Hunter joined by baseball betting expert Sean Zerillo. The trio breaks down the current landscape of Major League Baseball, analyzes the dominant Dodgers dynasty, explores how AI is revolutionizing sports betting models, and shares a host of actionable Opening Day and futures bets. The conversation covers how teams manage for October, the ever-changing baseball itself, and sports betting edges for the upcoming season, making this episode a must-listen for sharp baseball bettors.

Key Discussion Points & Insights

1. Baseball's Moment & The Dodgers Dynasty (03:19–16:02)

• State of MLB: Both hosts note MLB is in its healthiest, most exciting era since the steroid-fueled late '90s. Increased celebration, the energetic World Baseball Classic, and innovations like the pitch clock have all helped.
• Ohtani’s Impact: Simon highlights Shohei Ohtani's move to the Dodgers as transformative:

  “He is must-see TV... If you have not seen him hit or pitch, if you have an opportunity, you need to see this guy. It’s like seeing a superhero.” (06:06, Simon)

• Dodgers Odds & Philosophy:
  • Dodgers are absurd +220 favorites to win the World Series (15:10).
  • Their secret: focus on maximizing championship probability, not just daily wins. Dodger management prioritizes postseason roster health/rest over regular-season urgency, exemplified by load-managing stars and creatively utilizing the IL:

    “They’re load-managing Freeman. [Pitchers]—if they have any sort of concern about a pitching injury, they’ll just stick a guy in the IL.” (20:57, Sean Zerillo)

  • Historical dominance: “Dodgers haven’t won or paced fewer than a 91 season since 2013... If they win three in a row in this era, you’re talking about an all-time great team, not just a dynasty.” (19:28, Sean)

2. The Role of AI in Modern Sports Betting (08:08–15:10)

• AI as a Game Changer:
  Sean Zerillo and Simon discuss how AI is dramatically increasing efficiency for professional bettors:

  “Things that used to take me days, I can now do in hours... I can literally copy and paste all the lines... have [AI] find me my biggest edges.” (09:39, Sean)

• Use cases:
  • Automating line shopping and grading edges across books.
  • Enhancing and refining predictive models—AI helps layer in adjustments (e.g., factoring environment effects for Rockies hitters).
  • Simulations (Monte Carlo) and quicker coding without programming expertise.

    “The more you feed it, that’s the craziest part. The more you feed it, the better it gets. And that’s the scary part.” (13:26, Simon)

• Outlook:
  Both agree AI is still early-stage but quickly evolving. For now, it gives an edge to those willing to adapt (“Adapt or die.” 14:15, Sean) and makes certain aspects of handicapping easier and more scalable.

3. National League Futures & Value Plays (24:47–28:04)

• Postseason Landscape:
  • Usual suspects (Dodgers, Phillies, Braves, Mets, Cubs) likely take up playoff spots. The Braves’ rotation decimated by injury creates an opening for surprise teams.

    “The Braves have had the worst spring of any team... their rotation has fallen apart.” (24:47, Sean)

  • Surprise teams to target:
    • Marlins (+700) and Pirates (+300 to +450) as dark horse playoff bets.
  • Manager of the Year Derivative Angles:
    • Bet Pirates’ or Rays’ managers for Manager of the Year (15–20 to 1).

    “If either of those teams make the playoffs, their manager is almost certainly winning.” (27:10, Sean)

4. How the Changing Baseball Impacts Betting (32:53–40:16)

• Ball Changes & Impact on Scoring:
  • MLB has regularly altered baseballs’ composition, affecting drag and home run rates. 2022 was especially “egregious”—different balls were used at different times, with evidence juiced balls benefited Aaron Judge’s record chase:

    “MLB was putting a super juiced ball into play, the Goldilocks ball, for the Home Run Derby, All-Star Game, and games that Aaron Judge was playing.” (33:20, Sean)

  • Physics studies show these ball variations are real, not just theory.
• Conspiracy Theories:
  Simon relays rumors about big-market teams (Dodgers, Yankees, Phillies) getting more juiced balls, but Sean remains cautious about overstating these claims.

5. Sean Zerillo’s Futures Portfolio – Players and Props (40:16–47:20)

• Individual Futures & Milestone Props:

  • Kyle Schwarber to lead in RBI (35:1): “I made him 21:1 last year for RBI leader... still value at 35:1.” (40:39)
  • Shohei Ohtani RBI leader (14:1) and HR leader (5:1):

    “He’s above Aaron Judge for RBI... more projected value.” (41:36)

  • Milestone/Ladder Props:
    • More value on player milestone props (e.g., 200+ strikeouts at 10:1) than outright stat leader props.

• Longshot Pitcher Wins Plays:

  • Logan Webb (20:1), Framber Valdez (30:1), George Kirby (50:1)—compressed range of outcomes, so value in longer odds.

• Rookie of the Year Callout:

  • Kevin McGonigle (6:1, Tigers)—elite swing decisions, a skill under-appreciated by traditional “tools” models.
  • JJ Wetherholt (NL): Similar swing selectivity. Sean stresses these process-oriented prospects are high-floor ROY bets.

  “[McGonigle] is like the best prospect we’ve ever seen at those skills... His floor is incredibly high.” (45:28, Sean)

6. Best Bets for Opening Day (50:47–53:16)

• Big Edge:
  • Minnesota Twins ML at +130 (vs. Orioles, with Joe Ryan pitching), as Sean projects a coin flip; public/projection markets are too low on the Twins with Ryan on the mound.

    “I think they’re being under-projected right now... Twins opening day around +130ish—I probably like that down to about +115.” (50:59)

• Total Play:
  • Lean to Brewers–White Sox Under 8.5, projected 7.8.

Notable Quotes & Memorable Moments

• Dodgers Process:

  “Their greatest advantage is how they treat their roster... what can we do to increase our championship probability, not our probability of winning today.” – Sean Zerillo (16:02)

• AI's Inevitable Impact:

  “Adapt or die.” – Sean Zerillo (14:15)

• Swing Decisions as a New Frontier:

  “Swing decisions is the ability to swing at strikes and not at balls and to swing at good strikes and not close strikes... that is the process stat I think people overlook the most.” – Sean Zerillo (44:14)

Important Timestamps

• Intro, MLB excitement: 03:19–07:07
• AI in betting models: 08:08–15:10
• Dodgers dynasty/organizational philosophy: 15:10–20:57
• NL futures and sharp value plays: 24:47–28:04
• Ball changes/juiced balls discussion: 32:53–40:16
• Futures portfolio/player props: 40:16–47:20
• Opening Day best bets: 50:47–53:16

Final Thoughts

This episode mixes actionable futures advice with deep context on how both MLB teams and professional bettors are changing with the times—whether it's elite roster management or advanced analytics powered by AI. Zerillo's breakdowns make the Dodgers’ edge clear while also revealing under-the-radar value on teams like the Pirates or Marlins and player props driven by next-gen stats like “swing decisions.” Both casual fans and serious bettors will come away with not just picks, but with a sharper understanding of how to approach MLB in 2026.

Listen to Sharp or Square for more insights and subscribe for a steady edge on all things sports betting.