There was no shortage of inflammatory commentary during Donald Trump’s rally at New York’s Madison Square Garden on 27 October. But the owner of the venue was studiedly apolitical. “As a business, we are neutral in political matters. We rent to either side,” said an MSG representative. The stance reflects that of its boss, James Dolan, who runs much of the media, sports and entertainment empire started by his 98-year-old father Charles – the founder of pay TV channels Cablevision and HBO (both now sold). Assets these days include the New York Knicks and Rangers sports teams and the $2.3 billion Sphere arena in Las Vegas.
Dolan junior, 69, is a registered Democrat, notes The Hollywood Reporter. But he’s also a close friend of Trump’s of 30 years’ standing, who got married at his Mar-a-Lago resort in Florida. Described by New York magazine in 2005 as “excitable, prone to outbursts and tantrums” but “smart enough to know that doesn’t play well in the media”, Dolan has spent a lifetime working in his father’s shadow. Throughout much of his tenure as CEO of Cablevision, which began in 1995, there was speculation about who was really running the show. The two came to blows 20 years ago when they fell out over Charles Dolan’s cherished cash-haemorrhaging Voom satellite venture. Ultimately the son prevailed and Voom was shut down.
One of six children born to Charles and his wife Helen, Dolan grew up in considerable material comfort on Long Island. “He was a combustible kid who loved rock music and did everything he could to be around it, even if it meant working as a roadie in a garage band.” After drifting through two colleges, he eventually landed at SUNY-New Paltz, majoring in communications while taking guitar lessons on the side. A few days after graduation, he went to work for the family firm.
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“It was a ground-floor-up education”, involving peddling cable subs and selling advertising time. At one point he was despatched to Cleveland to launch an all-sports radio station. Nonetheless, the cracks were showing. Throughout his early adult life, Dolan battled drug and alcohol problems, later describing his mid-30s as “a festival of self-abuse”. He cleaned himself up and has been sober ever since.
By many accounts, Dolan’s short temper and inherent sense of entitlement have proved more difficult to manage. “At practically every step, he has been feuding with somebody,” says New York. His privileged background and bombastic style continue to “irk his detractors”, says the Financial Times. Sometimes with good reason. Dolan sparked an outcry in 2023 over his “dystopian” use of face-recognition software at Madison Square Garden – an effort “to stop lawyers working on litigation against his company from entering”.
What's next for James Dolan?
After a lifetime of being defined as his father’s son, Dolan is “finally getting credit as a visionary” for building the Sphere – a huge orb-shaped arena in Las Vegas “composed of a video-screen shell”, says the FT. But while undeniably a feat of “architectural artistry”, he is struggling “to square the circle on its finances”. Plans for global expansion, which include a deal to licence its IP to developers in Abu Dhabi, suffered a setback in 2023 when London mayor Sadiq Khan “put the kybosh” on a proposal to build a similar arena in Stratford on grounds that the flashing of 1.2 million exterior LED screens would be “disruptive” to residents. Whatever happens next, Dolan will always have the consolation of music and singing with his band, JD & the Straight Shot. Worth around $2 billion, he was described by the Deadspin blog site as “the richest touring musician in the world”. Dolan’s “musical talents”, however, concluded The New York Times after one performance, “are unlikely to endanger the day job”.
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