James Dolan's Unlikely Double Triumph: The Knicks' NBA Finals Run and the Sphere's Rise

James Dolan, the 71-year-old billionaire who has owned the New York Knicks since 1999, is experiencing a remarkable reversal of fortune after decades of embarrassment and dysfunction. The Knicks — who endured 16 losing seasons in a 19-year stretch under Dolan's stewardship and whose fans regularly chanted 'Sell the team' at Madison Square Garden — are now playing in the NBA Finals for the first time since 1999, meeting a champion caliber opponent just 27 years after their last appearance.

The turnaround hinges on a single strategic decision: Dolan stepping back. In 2020, he hired former agent Leon Rose as team president, and Rose systematically dismantled the franchise's addiction to expensive, past-their-prime stars. Instead, Rose assembled a roster of role players, elite defenders, and overlooked underdogs. The formula worked so well that the Knicks advanced one additional playoff round each successive year — conference semifinals, conference finals, and now the Finals — culminating in what was described as the biggest string of blowouts in playoff history during this postseason run. The team now stands four wins from its first championship since 1973.

Dolan's other headline-grabbing victory is the $2.3 billion Sphere venue in Las Vegas. The project looked catastrophic when it opened in 2023, having ballooned roughly $1 billion over budget. But by 2024, Sphere was generating more revenue than any other arena in the world, according to live music tracker Pollstar. Acts including the Eagles, Backstreet Boys, and Phish have filled the LED-covered dome, and a $100 million AI-enhanced immersive adaptation of 'The Wizard of Oz' became a cultural moment — with Dolan himself appearing at the premiere in an emerald green suit and top hat, embodying the wizard. Sphere Entertainment has since announced expansion plans in Abu Dhabi and National Harbor, Maryland.

The road to this moment was littered with spectacular failures and feuds. Dolan hired Isiah Thomas, who not only failed to produce a single playoff win but was found liable for sexual harassment in a 2007 jury verdict that cost Dolan and Madison Square Garden more than $11 million. He then brought in Phil Jackson, architect of the dynastic Chicago Bulls, to similar effect — no playoff wins. Dolan attempted to audit NBA finances under commissioner David Stern, creating a multi-year rift. He deployed facial recognition technology to bar perceived enemies from MSG. In 2023, he sued the Toronto Raptors, alleging they stole confidential files, and accused commissioner Adam Silver of being too close to Raptors ownership to arbitrate fairly. He once wrote a memo to fellow owners declaring the NBA neither needed nor wanted his opinion.

Now, the man who spent a quarter-century making enemies across professional basketball is four wins from sitting atop it — largely by learning to get out of the way.