Welcome to Beyond The Sideline, the community resource for the next generation of sports business leaders.
Big Idea
Billion-Dollar Loopholes: The Unregulated Rise of PrizePicks and Kalshi

In the ever-expanding universe of sports business, a new category of platform is rapidly gaining market share and raising complex questions for regulators. Companies like PrizePicks, Kalshi, and Polymarket have exploded in popularity, attracting millions of users and massive investment by operating in a space that blurs the lines between fantasy sports, financial markets, and traditional sports betting. While they argue they are not sportsbooks, their products often function as such, creating what many see as a de facto unregulated betting market for the masses.
And while regulators scramble to figure out how to classify them, they are making millions by living (or maybe hiding) in the gray area.
Legal
Pittsburgh Jock Tax Strikes Out

A recent unanimous decision by the Pennsylvania Supreme Court has sent a clear message to municipalities that rely on taxing visiting professional athletes and performers: the rules of the game have changed. By striking down the City of Pittsburgh's "jock tax" the court has not only dealt a financial blow to the city but has also set a significant precedent that could influence tax policy for cities across the country.
By The Numbers
Numbers That Jumped Off the Page
3.22 Million- The on-course action at the Ryder Cup didn't quite translate to blockbuster TV ratings, as the final day's broadcast on NBC and Peacock averaged just 3.22 million viewers, a 25-year low for a Ryder Cup held in the U.S. It seems the lack of a dramatic finish ultimately hurt viewership, proving that even for golf's most electric event, a close contest is key to keeping fans glued to their screens.
71 Million- The MLB is celebrating its third straight year of attendance growth, drawing over 71 million fans to ballparks this season. On top of that, national TV ratings are up by double digits, and the average age of a ticket buyer has dropped to 43, proving that faster games and exciting young stars are a winning combination.
$9 Billion- Just when you thought NFL franchise values couldn't get any higher, Robert Kraft has reportedly sold a minority stake in the New England Patriots in a deal that values the team at $9 billion, surpassing the recent record set by the Chicago Bears. It seems that six Super Bowl rings are worth their weight in gold, and then some.
Pulse Check
Last week, we asked BTS readers, “Who has the most leverage in today’s sports media negotiations?” Here’s what they thought.

Which furute expansion team's debut would you most want to attend?
The Highlight Reel
Catch up on our most-read articles from previous weeks
Do you have a topic you want us to cover, a survey question you'd like us to ask, or any news you'd like to share? Let us know at [email protected].
Looking for a new role? Subscribe to the BTS Job Roundup for a weekly summary of the hottest jobs across the business of sports.
/adver
Forward to other future sports business leaders




