Bloomberg Business of Sports: MLB Pitcher Betting Scandal, Juju Watkins’ Sports Ownership, SailGP’s Star Investors, and Serena Williams on Life After Tennis

Date: November 14, 2025
Hosts: Michael Barr, Vanessa Perdomo, Damian Sassower
Guests: Randall Williams (Bloomberg US Sports Business reporter), Gianluca Passi de Preposolo (Red Bull Italy SailGP Team Chairman), Danny Berger (Bloomberg TV anchor), Serena Williams (tennis legend)

Episode Overview

This episode dives deep into current, high-impact money-centric stories in sports. The hosts and their guests dissect the breaking MLB betting scandal involving pitchers, contextualize sweeping changes around athlete-investors, spotlight the growth and star-studded investment in SailGP racing, and end with an inspiring discussion with Serena Williams on her evolution from tennis star to headline-making businesswoman and investor.

1. Breaking News: MLB Pitchers Charged in Betting Scandal

Timestamps: 03:33–11:15

Key Points

Two Cleveland Guardians pitchers, Luis Ortiz and Emmanuel Classe, charged with fraud for allegedly manipulating pitches during MLB games.
Mirrors recent NBA betting scandals, putting both MLB and NBA under scrutiny regarding athletes’ gambling.
Federal evidence includes damning text exchanges during and after games.
Prop betting comes under renewed scrutiny, with growing calls for regulation or outright bans.
Discussion about the potential for leagues to reclaim paid contracts if criminal convictions are upheld.

Memorable Quotes

Randall Williams (03:57):
"The criminal sin, the cardinal sin of all the sports now is betting on it. And the fact that these guys are millionaires betting for thousands, it just never ceases to amaze me."
Randall Williams (06:11):
"On the MLB side, I read the entire case and they have text, they have exchanges from when the pitchers were on the mound and off the mound... the pictures are done. I mean, it's very damning evidence."
Vanessa Perdomo (07:39):
"Doesn't this just say that prop bets need to be really regulated? Like Adam Silver said after the NBA scandal had happened, we need to regulate prop bets in general. Should prop bets just go away?"
Randall Williams (09:50):
"[If convicted]... the NBA and MLB would just let the feds deal with it and then just push it away... Like you would rather just push both of all of the people who are allegedly involved as far into the corner so that they're out of sight."

Notable Segment

Text message evidence and in-game manipulation explained (07:01): Williams describes a pitcher intentionally throwing a ball in the dirt, followed by real-time betting communication – "the person that he was communicating with, texted him... maybe it was like a cat gif... They were both sad about the fact that they did not cash in."

Contextual Commentary

Hosts stress that the government’s involvement means the potential stakes are higher than mere league bans.
Prop bets' inherent manipulation risk discussed, especially with player stats.

2. College Athlete Ownership: Juju Watkins Buys Stake in NWSL Team

Timestamps: 11:15–14:26

Key Points

USC’s Juju Watkins becomes first college athlete with minority ownership in a pro sports team (NWSL’s Boston Legacy).
Move highlights the evolution of NIL (Name, Image, Likeness) deals and the growing financial clout of women’s basketball.
Hosts and Randall Williams discuss what leagues – and types of sports – will likely be open to college athlete investment.

Memorable Quotes

Michael Barr (11:15):
"If you want an idea on how college sports has changed... Juju Watkins... has bought a minority stake in the NWSL's Boston legacy. That you would never hear anything like that years ago."
Randall Williams (12:27):
"There is an interest in college sports ownership, period... When you talk about how much money that some of these people are making... it's shocking that the first person wasn't Caitlin Clark. And if it was not a woman at all, then your first guess probably would have been Shador Sanders or Arch Manning..."

Contextual Discussions

Emerging pathways for athlete empowerment, especially in women’s sports.
Regulatory limitations on college athlete ownership in different leagues.

3. SailGP: Big Investments, Global Expansion, and Unique Format

Timestamps: 17:44–30:16

Key Points

Interview with Gianluca Passi de Preposolo, co-owner of Red Bull Italy SailGP team.
SailGP conceived by Larry Ellison and Russell Coutts to fill the gap between America’s Cups. Now in its 5th season, the league has expanded rapidly.
Diverse and prominent ownership including Mark Lasry, Hugh Jackman, Ryan Reynolds, Kylian Mbappé, Sebastian Vettel, and Anne Hathaway.
SailGP is unique: one team per nation, mixed-gender crews, identically spec’d boats to maximize competitiveness.
The league's finals (“Grand Final”) in Abu Dhabi features a $2 million, winner-take-all purse.

Notable Quotes

Gianluca Passi de Preposolo (18:43):
"You have to consider that the America's Cup is the third oldest sport competition in the world after the Olympics and Royal Ascot... what Larry Ellison understood... you could start a new league getting the best ideas from all the sports league out there."
Damian Sassower (23:49):
"We keep mentioning Larry Ellison... but I'm going to go even further... Hugh Jackman and Ryan Reynolds, Kylian Mbappé... Sebastian Vettel... Anne Hathaway is somehow involved with you and the Italian team. These aren't just nobodies."
Gianluca Passi de Preposolo (25:10):
"It's 15 minutes per race, back to back. And then on Sunday there is the final... in Abu Dhabi is going to be the season final for the last three teams, and they're going to compete for the big prize that is $2 million."
Gianluca Passi de Preposolo (28:58):
"The five characteristics... men and women on the same team... only one boat per nation... every boat is exactly the same by the millimeter... spectacular locations around the world... expense cap."

Fun Segment

The U.S. team’s negative score discussed humorously due to SailGP’s penalty system (26:34).

4. Serena Williams: From Tennis Legend to Venture Investor

Timestamps: 33:33–45:35

Key Points

Extended segment with Serena Williams (interviewed by Danny Berger) exploring her identity as a businesswoman and transition post-tennis.
Williams describes always seeing herself as an entrepreneur, crediting her father for instilling the value of a “plan B.”
She started investing during her tennis career—famously taking calls with investors before Wimbledon matches.
Williams says today’s athlete is expected to have a side hustle; when she began, such ambition was "frowned upon."
Her firm, Serena Ventures, focuses on “investing for the 98%” — women, minorities, and everyday consumers, not just elites.
All Serena’s portfolio companies must have an AI plan.
Williams owns stakes in the Miami Dolphins and the new Toronto WNBA team; her daughter, Olympia, is also a co-owner of Angel City FC and possibly the Toronto WNBA team.
Segment addresses the challenges and skepticism celebrity-led VC funds face in today’s tight money environment.

Memorable Quotes

Serena Williams (33:50):
"My job was a business... it wasn't for me just about going out there and hitting tennis balls and winning... it was also really about being a business, being an entrepreneur."
Serena Williams (34:14):
"I was taught from an early age, actually from my father, that it was really important to have a plan B."
Serena Williams (35:10):
"Now, the new modern athlete, if they're only playing their sport, then now that's frowned upon."
Danny Berger (37:41):
"[Serena] tells this story about her walking to the center court at Wimbledon on the phone with an investor... and the investor being like, hey, where are you, by the way? And she was like, I was just about to go play at Wimbledon."
Danny Berger (39:44):
"She said that all of the companies that she invests in need to have an AI plan."
Serena Williams, via Danny Berger (44:41):
"I want my daughter to see impressive women doing impressive things... There are just not a lot of women. You go to these conferences, they tend to be white men. They tend to have very similar backgrounds. And you can't think of a more different background than Serena Williams."

Context and Impact

The interview frames Williams’ investments as mission-driven, emphasizing breaking barriers for women and minorities in business and sports.
Discusses the evolving landscape for athlete-investors and the increased expectations for modern athletes.

Notable Moments & Quotes (With Timestamps)

On the shocking nature of the MLB betting scandal:
Randall Williams (03:57) — "The criminal sin, the cardinal sin of all the sports now is betting on it... these guys are millionaires betting for thousands, it just never ceases to amaze me."
On the personal aspect of SailGP investment:
Gianluca Passi de Preposolo (22:33) explains the serendipitous family connection that fueled his entry into the league.
On Serena Williams' business acumen:
Danny Berger (37:41) — "She started investing while she was still playing tennis. She tells this story about her walking to the center court at Wimbledon on the phone with an investor..."
On athlete side hustles and VC struggles:
Danny Berger (41:20) — "It used to be that anybody could start a fund and you have celebrity power... I think it's a little bit more difficult to do that at the moment."
On representation and setting an example for her daughter:
Danny Berger quoting Serena (44:41) — "I want my daughter to see impressive women doing impressive things... it gives young women out there... [the chance to say] 'well, hell, I want to do that.'"

Segment Timestamps Quick Reference

MLB Pitching Scandal: 03:33–11:15
Juju Watkins Team Ownership: 11:15–14:26
SailGP / Gianluca Passi de Preposolo: 17:44–30:16
Serena Williams / Danny Berger Interview: 33:33–45:35

Summary Takeaways

Integrity in Sports: Federal prosecutions are a game-changer compared to mere league discipline as betting scandals escalate.
Athlete Investors: The era of college and pro athletes as business owners is real, and women’s sports are leading the way.
Sports Ownership’s New Era: SailGP is attracting A-list investors and breaking traditional molds with gender-integrated, nationally branded, but internationally staffed teams.
Serena Williams' Legacy: She embodies the blueprint for the new “modern athlete"—multi-dimensional, entrepreneurial, and committed to social impact. Her push for women and minorities in investing sends a powerful message to the next generation.

This episode is must-listen for anyone following sports business, athlete entrepreneurship, or the evolution of integrity in sports in a rapidly changing, high-stakes environment.

Bloomberg Business of Sports: MLB Pitcher Betting Scandal, Juju Watkins’ Sports Ownership, SailGP’s Star Investors, and Serena Williams on Life After Tennis

Episode Overview

1. Breaking News: MLB Pitchers Charged in Betting Scandal

Timestamps: 03:33–11:15

Key Points

Two Cleveland Guardians pitchers, Luis Ortiz and Emmanuel Classe, charged with fraud for allegedly manipulating pitches during MLB games.
Mirrors recent NBA betting scandals, putting both MLB and NBA under scrutiny regarding athletes’ gambling.
Federal evidence includes damning text exchanges during and after games.
Prop betting comes under renewed scrutiny, with growing calls for regulation or outright bans.
Discussion about the potential for leagues to reclaim paid contracts if criminal convictions are upheld.

Memorable Quotes

Randall Williams (03:57):
"The criminal sin, the cardinal sin of all the sports now is betting on it. And the fact that these guys are millionaires betting for thousands, it just never ceases to amaze me."
Randall Williams (06:11):
"On the MLB side, I read the entire case and they have text, they have exchanges from when the pitchers were on the mound and off the mound... the pictures are done. I mean, it's very damning evidence."
Vanessa Perdomo (07:39):
"Doesn't this just say that prop bets need to be really regulated? Like Adam Silver said after the NBA scandal had happened, we need to regulate prop bets in general. Should prop bets just go away?"
Randall Williams (09:50):
"[If convicted]... the NBA and MLB would just let the feds deal with it and then just push it away... Like you would rather just push both of all of the people who are allegedly involved as far into the corner so that they're out of sight."

Notable Segment

Text message evidence and in-game manipulation explained (07:01): Williams describes a pitcher intentionally throwing a ball in the dirt, followed by real-time betting communication – "the person that he was communicating with, texted him... maybe it was like a cat gif... They were both sad about the fact that they did not cash in."

Contextual Commentary

Hosts stress that the government’s involvement means the potential stakes are higher than mere league bans.
Prop bets' inherent manipulation risk discussed, especially with player stats.

2. College Athlete Ownership: Juju Watkins Buys Stake in NWSL Team

Timestamps: 11:15–14:26

Key Points

USC’s Juju Watkins becomes first college athlete with minority ownership in a pro sports team (NWSL’s Boston Legacy).
Move highlights the evolution of NIL (Name, Image, Likeness) deals and the growing financial clout of women’s basketball.
Hosts and Randall Williams discuss what leagues – and types of sports – will likely be open to college athlete investment.

Memorable Quotes

Michael Barr (11:15):
"If you want an idea on how college sports has changed... Juju Watkins... has bought a minority stake in the NWSL's Boston legacy. That you would never hear anything like that years ago."
Randall Williams (12:27):
"There is an interest in college sports ownership, period... When you talk about how much money that some of these people are making... it's shocking that the first person wasn't Caitlin Clark. And if it was not a woman at all, then your first guess probably would have been Shador Sanders or Arch Manning..."

Contextual Discussions

Emerging pathways for athlete empowerment, especially in women’s sports.
Regulatory limitations on college athlete ownership in different leagues.

3. SailGP: Big Investments, Global Expansion, and Unique Format

Timestamps: 17:44–30:16

Key Points

Interview with Gianluca Passi de Preposolo, co-owner of Red Bull Italy SailGP team.
SailGP conceived by Larry Ellison and Russell Coutts to fill the gap between America’s Cups. Now in its 5th season, the league has expanded rapidly.
Diverse and prominent ownership including Mark Lasry, Hugh Jackman, Ryan Reynolds, Kylian Mbappé, Sebastian Vettel, and Anne Hathaway.
SailGP is unique: one team per nation, mixed-gender crews, identically spec’d boats to maximize competitiveness.
The league's finals (“Grand Final”) in Abu Dhabi features a $2 million, winner-take-all purse.

Notable Quotes

Gianluca Passi de Preposolo (18:43):
"You have to consider that the America's Cup is the third oldest sport competition in the world after the Olympics and Royal Ascot... what Larry Ellison understood... you could start a new league getting the best ideas from all the sports league out there."
Damian Sassower (23:49):
"We keep mentioning Larry Ellison... but I'm going to go even further... Hugh Jackman and Ryan Reynolds, Kylian Mbappé... Sebastian Vettel... Anne Hathaway is somehow involved with you and the Italian team. These aren't just nobodies."
Gianluca Passi de Preposolo (25:10):
"It's 15 minutes per race, back to back. And then on Sunday there is the final... in Abu Dhabi is going to be the season final for the last three teams, and they're going to compete for the big prize that is $2 million."
Gianluca Passi de Preposolo (28:58):
"The five characteristics... men and women on the same team... only one boat per nation... every boat is exactly the same by the millimeter... spectacular locations around the world... expense cap."

Fun Segment

The U.S. team’s negative score discussed humorously due to SailGP’s penalty system (26:34).

4. Serena Williams: From Tennis Legend to Venture Investor

Timestamps: 33:33–45:35

Key Points

Extended segment with Serena Williams (interviewed by Danny Berger) exploring her identity as a businesswoman and transition post-tennis.
Williams describes always seeing herself as an entrepreneur, crediting her father for instilling the value of a “plan B.”
She started investing during her tennis career—famously taking calls with investors before Wimbledon matches.
Williams says today’s athlete is expected to have a side hustle; when she began, such ambition was "frowned upon."
Her firm, Serena Ventures, focuses on “investing for the 98%” — women, minorities, and everyday consumers, not just elites.
All Serena’s portfolio companies must have an AI plan.
Williams owns stakes in the Miami Dolphins and the new Toronto WNBA team; her daughter, Olympia, is also a co-owner of Angel City FC and possibly the Toronto WNBA team.
Segment addresses the challenges and skepticism celebrity-led VC funds face in today’s tight money environment.

Memorable Quotes

Serena Williams (33:50):
"My job was a business... it wasn't for me just about going out there and hitting tennis balls and winning... it was also really about being a business, being an entrepreneur."
Serena Williams (34:14):
"I was taught from an early age, actually from my father, that it was really important to have a plan B."
Serena Williams (35:10):
"Now, the new modern athlete, if they're only playing their sport, then now that's frowned upon."
Danny Berger (37:41):
"[Serena] tells this story about her walking to the center court at Wimbledon on the phone with an investor... and the investor being like, hey, where are you, by the way? And she was like, I was just about to go play at Wimbledon."
Danny Berger (39:44):
"She said that all of the companies that she invests in need to have an AI plan."
Serena Williams, via Danny Berger (44:41):
"I want my daughter to see impressive women doing impressive things... There are just not a lot of women. You go to these conferences, they tend to be white men. They tend to have very similar backgrounds. And you can't think of a more different background than Serena Williams."

Context and Impact

The interview frames Williams’ investments as mission-driven, emphasizing breaking barriers for women and minorities in business and sports.
Discusses the evolving landscape for athlete-investors and the increased expectations for modern athletes.

Notable Moments & Quotes (With Timestamps)

On the shocking nature of the MLB betting scandal:
Randall Williams (03:57) — "The criminal sin, the cardinal sin of all the sports now is betting on it... these guys are millionaires betting for thousands, it just never ceases to amaze me."
On the personal aspect of SailGP investment:
Gianluca Passi de Preposolo (22:33) explains the serendipitous family connection that fueled his entry into the league.
On Serena Williams' business acumen:
Danny Berger (37:41) — "She started investing while she was still playing tennis. She tells this story about her walking to the center court at Wimbledon on the phone with an investor..."
On athlete side hustles and VC struggles:
Danny Berger (41:20) — "It used to be that anybody could start a fund and you have celebrity power... I think it's a little bit more difficult to do that at the moment."
On representation and setting an example for her daughter:
Danny Berger quoting Serena (44:41) — "I want my daughter to see impressive women doing impressive things... it gives young women out there... [the chance to say] 'well, hell, I want to do that.'"

Segment Timestamps Quick Reference

MLB Pitching Scandal: 03:33–11:15
Juju Watkins Team Ownership: 11:15–14:26
SailGP / Gianluca Passi de Preposolo: 17:44–30:16
Serena Williams / Danny Berger Interview: 33:33–45:35

Summary Takeaways

Integrity in Sports: Federal prosecutions are a game-changer compared to mere league discipline as betting scandals escalate.
Athlete Investors: The era of college and pro athletes as business owners is real, and women’s sports are leading the way.
Sports Ownership’s New Era: SailGP is attracting A-list investors and breaking traditional molds with gender-integrated, nationally branded, but internationally staffed teams.
Serena Williams' Legacy: She embodies the blueprint for the new “modern athlete"—multi-dimensional, entrepreneurial, and committed to social impact. Her push for women and minorities in investing sends a powerful message to the next generation.

This episode is must-listen for anyone following sports business, athlete entrepreneurship, or the evolution of integrity in sports in a rapidly changing, high-stakes environment.

MLB Pitchers Charged in a New Betting Scheme; Serena Williams at the American Business Forum

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Summary

Bloomberg Business of Sports: MLB Pitcher Betting Scandal, Juju Watkins’ Sports Ownership, SailGP’s Star Investors, and Serena Williams on Life After Tennis

Episode Overview

1. Breaking News: MLB Pitchers Charged in Betting Scandal

Key Points

Memorable Quotes

Notable Segment

Contextual Commentary

2. College Athlete Ownership: Juju Watkins Buys Stake in NWSL Team

Key Points

Memorable Quotes

Contextual Discussions

3. SailGP: Big Investments, Global Expansion, and Unique Format

Key Points

Notable Quotes

Fun Segment

4. Serena Williams: From Tennis Legend to Venture Investor

Key Points

Memorable Quotes

Context and Impact

Notable Moments & Quotes (With Timestamps)

Segment Timestamps Quick Reference

Summary Takeaways

Summary

Bloomberg Business of Sports: MLB Pitcher Betting Scandal, Juju Watkins’ Sports Ownership, SailGP’s Star Investors, and Serena Williams on Life After Tennis

Episode Overview

1. Breaking News: MLB Pitchers Charged in Betting Scandal

Key Points

Memorable Quotes

Notable Segment

Contextual Commentary

2. College Athlete Ownership: Juju Watkins Buys Stake in NWSL Team

Key Points

Memorable Quotes

Contextual Discussions

3. SailGP: Big Investments, Global Expansion, and Unique Format

Key Points

Notable Quotes

Fun Segment

4. Serena Williams: From Tennis Legend to Venture Investor

Key Points

Memorable Quotes

Context and Impact

Notable Moments & Quotes (With Timestamps)

Segment Timestamps Quick Reference

Summary Takeaways