Who Are The Executives?

Leadership at Sphere is also raising red flags for me.

Here's why James Dolan, CEO of Sphere Entertainment, Might Be a Problematic Business Partner

James L. Dolan—Executive Chairman & CEO of Sphere Entertainment Co., MSG Sports, MSG Entertainment, and MSG Networks—is undeniably a high-profile billionaire with deep roots in the media and entertainment world. But beneath the flashy veneer of arenas and concerts lies a track record that raises serious concerns about his leadership, judgment, and ethics.

1. Allegations of Sexual Assault and Trafficking

In early 2024, Kellye Croft, a former massage therapist, filed a sweeping federal lawsuit accusing Dolan of sexual assault, trafficking, and arranging for her to be sexually assaulted by Harvey Weinstein—describing conduct that she says occurred around 2013–2014 while Dolan’s band was touring with the Eagles. These are grave, disturbing allegations. Dolan denies them, and while a judge dismissed the lawsuit later in 2024, the claims remain disquieting and were legally complex. Some counts were dismissed without prejudice, meaning they could be refiled.

2. Leying Reputation in Team Management

Dolan’s tenure as owner of the New York Knicks has been marred by mismanagement. The team endured long playoff droughts and poor decision-making, notably involving disastrous free-agent signings. NBA Commissioner David Stern once criticized the Knicks under Dolan, saying they “are not a model of intelligent management.” Fans and analysts alike have labeled his leadership “petty” and autocratic.

He’s also had a long-standing reputation for being thin-skinned and punitive—famously banning fans who demanded he sell the team and, more controversially, using facial recognition technology at MSG venues to bar attorneys involved in legal cases against him, even when they had valid tickets.

3. Corporate Governance and Conflicts of Interest

In 2019, shareholders sued Dolan, claiming his compensation at MSG was grossly excessive and distracting—alleging he spent too much time focusing on his band (JD & The Straight Shot... which is kinda cool lol) rather than his CEO duties. The lawsuit challenged his multimillion-dollar pay compared to peers; while investor courts dismissed the case, the narrative stood.

This intertwining of personal passion and business responsibilities fuels concerns about governance. His close family control over MSG entities—combined with opaque decisions like mergers, spin-offs, and media suppressions—makes it hard to separate his personal interests from corporate strategy.

I'm not sure the validity of these complaints, but I don't like to see it as a potential investor. Buffett once said, "you can't do a good deal with a bad person". Before I'd even consider taking a position in Sphere, I'd need to really vet James Dolan.