Media mogul James Dolan takes straight shot at the limelight
Controversial media mogul James Dolan has been hailed as a visionary for his Sphere arena in Las Vegas. But can he square the circle financially?
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.
Subscribe to MoneyWeek
Subscribe to MoneyWeek today and get your first six magazine issues absolutely FREE
Sign up to Money Morning
Don't miss the latest investment and personal finances news, market analysis, plus money-saving tips with our free twice-daily newsletter
Don't miss the latest investment and personal finances news, market analysis, plus money-saving tips with our free twice-daily newsletter
“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”.
This article was first published in MoneyWeek's magazine. Enjoy exclusive early access to news, opinion and analysis from our team of financial experts with a MoneyWeek subscription.
Sign up to Money Morning
Our team, led by award winning editors, is dedicated to delivering you the top news, analysis, and guides to help you manage your money, grow your investments and build wealth.
Jane writes profiles for MoneyWeek and is city editor of The Week. A former British Society of Magazine Editors editor of the year, she cut her teeth in journalism editing The Daily Telegraph’s Letters page and writing gossip for the London Evening Standard – while contributing to a kaleidoscopic range of business magazines including Personnel Today, Edge, Microscope, Computing, PC Business World, and Business & Finance.
She has edited corporate publications for accountants BDO, business psychologists YSC Consulting, and the law firm Stephenson Harwood – also enjoying a stint as a researcher for the due diligence department of a global risk advisory firm.
Her sole book to date, Stay or Go? (2016), rehearsed the arguments on both sides of the EU referendum.
She lives in north London, has a degree in modern history from Trinity College, Oxford, and is currently learning to play the drums.
-
Investors pulled £4.2bn from equity funds ahead of Budget tax raid
October was the third-worst month on record for fund flows, new figures show, as investors sold assets ahead of the Autumn Budget
By Katie Williams Published
-
What Keir Starmer's ‘Plan for Change’ means for you - six milestones explained
Prime Minister Keir Starmer has set out six milestones that the public can judge the government by - we reveal Labour's top policy targets
By Marc Shoffman Published
-
Justin Sun: China’s revolutionary crypto visionary
Justin Sun, founder of the Tron blockchain and cryptocurrency made his fortune young from bitcoin trades. Now he wants to change the world
By Jane Lewis Published
-
Why Gary Lineker's Match of the Day exit matters
Former England captain Gary Lineker is stepping down from hosting the football programme Match of the Day, after 25 years.
By Jane Lewis Published
-
Henry Keswick: the plutocrat who fell for China
Profile Henry Keswick, a scion of the Jardine Matheson trading company, rebuilt the firm's fortunes after the upheavals of the 1990s. He died aged 86.
By Jane Lewis Published
-
Vaccine stocks slump after RFK Jr picked as Trump's health secretary
Drugmakers' shares slumped after RFK Jr, a vaccine sceptic, was appointed as the next US Health Secretary. How will this affect drug companies?
By Dr Matthew Partridge Published
-
Elon Musk enters the White House – what happens now?
Elon Musk has achieved the seemingly impossible many times before in the business world. But will he be able to cut the US government down to size?
By Jane Lewis Published
-
Sri Mulyani Indrawati: Indonesia’s Iron Lady
Keeping Sri Mulyani Indrawati on as Indonesia's finance minister has steadied the ship after the election of a former military general spooked financial markets
By Jane Lewis Published
-
What Trump's presidential election win means for the US economy
What will Trump's US presidential election win actually mean for Americans and the rest of the world?
By Stuart Watkins Published
-
US election – is the Trump Trade back?
The US election is around the corner. How does Trump influence US markets?
By Alex Rankine Published