Bloomberg Business of Sports — Episode Summary

Date: December 5, 2025
Episode: Lane Kiffin's Ole Miss Exit; Cain CEO Jonathan Goldstein Talks Sports Investing
Host(s): Michael Barr, Damian Sassauer, Vanessa Perdomo

Episode Overview

This episode dives into some of the biggest money moves and trends shaping the modern sports industry, with a focus on three central topics:

1. Lane Kiffin’s dramatic exit from Ole Miss for LSU and college football’s shifting landscape
2. The evolution and regulation of sports betting, featuring BetMGM CEO Adam Greenblatt
3. How real estate giant Cain International is investing in sports, with CEO Jonathan Goldstein

I. Lane Kiffin's Exit—Disruption in College Football

[Starts ~02:22]

Main Theme

• Lane Kiffin leaves Ole Miss in the middle of a potential playoff run to take the head job at LSU, sparking debates about loyalty, the coaching carousel, and the state of college football.

Key Discussion Points

• Kiffin’s Pattern of Drama:
  • “None of what Lane Kiffin has done over the course of his career has surprised me. He's an agent of chaos in the chaotic world of college sports.”
    — Randall Williams [03:26]
• Coaching Transience & Transfer Portal:
  • Athletes and coaches now share career instability and movement.
  • “When athletes can up and leave and enter the transfer portal … coaches have long been able to switch jobs or be fired with payouts — I think this is just the world we live in and everybody needs to get over it.”
    — Randall Williams [03:26]
• Calendar Chaos vs. Personal Choice:
  • Ben Portnoy critiques those who blame the timing on college sports schedules:
  • “To say that this is not essentially entirely out of Lane Kiffin's doing, I think is kind of disingenuous.”
    [06:30]
  • The conflict between the university academic calendar and football operations is “just how this works.”
• Broader Playoff Implications:
  • How commissioner preferences and broadcast contracts affect the future playoff format (i.e., 12, 14, 16, or 24 teams). Ongoing negotiations and TV deals mean expansion may be stalled.
  • “The College Football Playoff is going to continue to be a conversation … There's not exactly optimism that anything's going to get done and that anything would change.”
    — Ben Portnoy [07:44]
  • “You're in a tight window as far as where you can put these games. Obviously, you're going head to head with the NFL.”
    — Ben Portnoy [09:10]

Notable Quotes

• “Lane is chaotic and we can all agree on that. … I remember saying when Lane got hired at Ole Miss, this is basically going to go one of two ways: either up in smoke because it doesn’t work, or up in smoke because he does so well and goes somewhere else—and the exit will be fiery.”
  — Ben Portnoy [04:11]
• On the NCAA’s weakening power:
  • “I think the Power 4 conferences ultimately have sort of the absolute power ‘over the ecosystem and what shape it’s going to take.’”
    — Ben Portnoy [11:19]

II. The State & Future of Sports Betting

[Starts ~17:02]

Main Theme

• Confronting scandal, regulatory challenges, and the impact of prediction markets on the sports betting landscape, with insight from BetMGM CEO Adam Greenblatt.

Key Discussion Points

• Impact of Betting Scandals:
  • “These kind of scandals are bad for sport, bad for the industry … but bettors are still showing up. Last week was one of our best weeks in the history of BetMGM.”
    — Adam Greenblatt [18:22]
• Integrity & Regulation:
  • BetMGM works with leagues and regulators to detect suspicious activity and promote responsible gambling.
• Prop Bets & Offshore Markets:
  • Concern over outright bans on player prop bets: “If the legal market says they're not allowed … players go to the illegal offshore markets.”
    — Adam Greenblatt [20:08]
• Prediction Markets as Competition:
  • “We don’t see prediction markets as meaningful long-term threat to our business… our offering and value proposition is just better.”
    — Adam Greenblatt [23:18]
  • BetMGM will monitor new legislative movements but remains focused on regulated markets.
• Women’s Sports Betting Growth:
  • “One of the reasons why we've seen such explosive growth in interest in women's sports is because of the quality of players and the star appeal. … But we do want to follow where the demand is.”
    — Adam Greenblatt [28:09]

Notable Quotes & Moments

• “Our analysis, which is shared by mid-30s Attorneys General and consistently by our regulators, is that … prediction markets in sports prediction contracts are frankly illegal sports betting.”
  — Adam Greenblatt [26:33]
• On platform growth:
  • “Missouri represents our 30th market … We now reach 50% of the US population.”
    — Adam Greenblatt [22:24]
• “Being a customer of BetMGM is more rewarding than participating in the prediction markets.”
  — Adam Greenblatt [23:36]

III. Investing in Sports Infrastructure & Experiences: Cain International

[Starts ~32:31]

Main Theme

• How a real estate asset manager leverages experiential, multi-use development in sports and entertainment, as explained by CEO Jonathan Goldstein.

Key Discussion Points

• Cain’s Sports Investment Strategy:
  • Stakes in Chelsea FC, LA Dodgers, Lakers, and non-traditional sports concepts (Swingers mini-golf, The St. James sports complex).
  • “There is a huge, huge desire in the marketplace for this fusion of performance, of wellness, of health, of experiences.”
    — Jonathan Goldstein [34:07]
• Brand-Building Around Experience:
  • “We’ve approached the marketplace from a slightly different perspective … from the asset level, but also from the brand level. … You have to understand what you’re delivering to that customer as if it were you.”
    — Jonathan Goldstein [37:32]
• Multi-Use Development and Stadiums:
  • Modern sports venues designed to be entertainment destinations “365 days a year” (concerts, events beyond sports).
• International Trends: Cricket & Media Rights:
  • The Indian Premier League’s media rights eclipse most North American leagues on a per-game basis.
  • “When you look on a broadcast basis, the IPL is second only to the NFL in broadcasting rights, value per game.”
    — Jonathan Goldstein [41:15]
  • Explanation of “The Hundred” (short-format English cricket) as a potential model for US sports.

Notable Quotes

• “You've not lived your Life until you've walked in the shoes of the other man. … That's the way we've approached our brands, our hotels, and our sports facilities: as the user.”
  — Jonathan Goldstein [37:33]
• “I think the whole thing about sport is creating those experiences that are just not replicable.”
  — Jonathan Goldstein [43:16]
• “Every member of the team is important ... we're all on a team, and we are only as strong as the weakest part of our team.”
  — Jonathan Goldstein [44:03]

Memorable Moment

• Michael Barr draws a parallel between cricket’s Hundred and baseball:
  • “I like that—imagine a baseball game where each side gets 100 pitches. … You wouldn’t have pitchers being accused of wasting pitches!”
    [41:59; 42:51]

Timestamps for Notable Segments

• [02:22] — Opening to Lane Kiffin's exit and coaching carousel
• [04:11] — Ben Portnoy discusses Lane Kiffin’s reputation & the SEC
• [07:44] — Playoff expansion debate and TV contracts
• [11:19] — The NCAA’s waning influence in college sports
• [17:02] — Sports betting segment: Introducing BetMGM CEO Adam Greenblatt
• [18:22] — Impact of betting scandals on the industry
• [20:08] — Legal market vs. offshore/illegal betting
• [23:18] — Prediction markets and the regulatory future
• [28:09] — Women’s sports betting trends
• [32:31] — Cain International's investments and sports strategy
• [36:37] — Multi-use real estate & brand experience
• [41:15] — IPL broadcast rights & The Hundred explained
• [44:03] — Teamwork as a life/sports lesson
• [44:21] — Closing out with thanks and final takeaways

Takeaways

• Coaching instability and high-profile moves are now baked into the financial and cultural DNA of college sports.
• The sports betting landscape is expanding but also facing new regulatory hurdles, competition from prediction markets, and concerns over integrity.
• Real estate and fan experience are at the heart of sports investment, with the most successful ventures designing spaces and brands that serve audiences year-round, not just on game day.
• The sports media rights market is truly global—the IPL is a remarkable example of a non-U.S. league commanding top-dollar, especially on a per-game basis.
• Sports, at every level, reflect deeper lessons about economics, teamwork, and the need for constant adaptation.

Notable Quotes

• “You've not lived your Life until you've walked in the shoes of the other man.”
  (Jonathan Goldstein, 37:33)
• “Our analysis … is that prediction markets in sports prediction contracts are frankly illegal sports betting.”
  (Adam Greenblatt, 26:33)
• “The way that it's worked, right, is that, you know, Lane is leaving Ole Miss in the middle of a playoff run to go to LSU, a place that, you know, he thinks he can go win a national championship, essentially.”
  (Ben Portnoy, 04:11)

For listeners and industry insiders, this episode delivers a comprehensive, colorful tour of the dynamics shaping sports business today—from the chaos of college football coaching moves to the investment strategies transforming stadiums and sports betting.