Dolan is married and resides on Long Island with his wife. He is the son of Cablevision founder Charles Dolan and nephew of Cleveland Indians owner Larry Dolan. Dolan's two brothers, Patrick and Thomas, serve on Cablevision's Board of Directors. Dolan is of Irish descent.
After originally pursuing a career in music, Dolan eventually switched to a major in communications at SUNY New Paltz and began working for Cablevision in various capacities including sales before eventually being dispatched to Cleveland by his father to manage the launching of a sports radio station. In 1995, he was made CEO of Cablevision.
Throughout his early adult life, Dolan battled drug and alcohol problems and was reportedly known for having a volatile temper. In 1993, he went to drug rehabilitation at the Hazelden clinic in Center City, Minnesota.
Dolan performs blues-inspired rock as the singer for JD & The Straight Shot and is also an avid sailor.
Dolan was an ardent opponent of his father's proposed Voom satellite service, which became a polarizing controversy among Cablevision's Board of Directors. While supporters argued Voom could propel Cablevision into the future emerging satellite market and a wider customer base, opponents of the plan, including James Dolan, argued it was too expensive with no expense relief for the foreseeable future. In the end, the younger Dolan prevailed and Voom was shut down. This was an instrumental event in Dolan emerging from his father's shadow, albeit reluctantly, as a viable businessman.
However, his business career has not been without failures, which include purchasing the failing Wiz electronics and entertainment chain which ended up posting losses of $250 million before being liquidated and the Clearview Cinemas chain which has failed to generate any significant revenue.
Dolan is also dedicated to Cablevision's philanthropic partnership with The Lustgarten Foundation, the nation's largest private supporter of pancreatic cancer research. Together with Charles Dolan and former Cablevision Vice Chairman and Madison Square Garden Chairman Marc Lustgarten. Dolan established the Foundation in 1998. In 2008, Cablevision made a multi-year commitment to underwrite the Foundation's costs, ensuring that 100 percent of every donation goes directly to researching this deadly disease. With Dolan's backing, Cablevision also uses its assets to advance the curePC campaign, aimed at increasing public awareness of pancreatic cancer, and is responsible for organizing the Holiday Rock & Roll Bash, the Foundation's biggest annual fundraiser.
Dolan also led MSG's response to local and national tragedies. He played a principal role in organizing the recent "12-12-12" benefit concert, which raised an initial $50 million for the victims of Hurricane Sandy, with additional money still coming in. Other extraordinary benefit concerts have included "The Concert For New York City," which generated more than $35 million in aid for 9/11 victims and heroes, and "From The Big Apple to The Big Easy," which raised nearly $9 million for Hurricane Katrina relief. Dolan also supports MSG's ongoing commitment to the community, particularly through the Garden of Dreams Foundation, the non-profit charity that partners with MSG to help children facing obstacles throughout the New York metropolitan area.
In 1994, Paramount Communications, the owner of Madison Square Garden, was acquired by Viacom, who in turn sold the MSG properties to Cablevision and ITT Corporation, which had 50% ownership each. ITT sold its share to Cablevision three years later.
In 1999, Dolan was given an increased role in managing Cablevision's sports properties and is now the primary manager of these assets. The teams under his domain include most notably the National Basketball Association's New York Knicks, the National Hockey League's New York Rangers, the Women's National Basketball Association's New York Liberty, and the American Hockey League's Hartford Wolf Pack.
As Chairman of Madison Square Garden, he supervises day-to-day operations of its professional sports teams and regional sports networks, which include MSG Network and MSG Plus. He also serves as a governor of the Knicks and Rangers to their respective leagues.
Like the Rangers, the Knicks performed abysmally in the early 2000s and have yet to recover, which fans mostly blame on Dolan's management missteps. Although the Knicks made the NBA Finals in 1999, they have not posted a winning season until the 2012-2013 season. Furthermore, the Knicks had not made the playoffs from the 2003-2004 season to the 2010-2011 season, which both ended in first round four game sweeps for the Knicks. Dolan has come under fire from many Knicks' fans for the team's run of consecutive losing seasons from 2001-2002 to 2009-2010. Numerous media and informal fan polls, including a recent Sports Illustrated poll, have ranked Dolan the worst owner in the NBA. In 2007, NBA Commissioner David Stern criticized Dolan's management of the Knicks, saying "they're not a model of intelligent management." One widely criticized decision was to give shooting guard Allan Houston a 6-year, $100 million maximum contract in 2001, when no other team had offered Houston more than $75 million. Houston retired due to injury after just four seasons and with over $40 million remaining on his contract.
In 2003, Dolan hired Isiah Thomas as Team President of Basketball Operations and General Manager to replace embattled executive Scott Layden. Thomas made aggressive moves to re-tool and upgrade the Knicks roster through trades, the NBA Draft, and free agency. Despite the talent Thomas imported, the team did not perform up to expectations and Thomas was often the target of the frustration of Knick fans; Dolan was also on the receiving end of the ire of Knicks' fans for his commitment to Thomas in spite of Thomas' sometimes questionable decisions.
After the 2004-2005 season, the Knicks signed head coach Larry Brown to a 5-year, $50 million contract. After just one (losing) season, Brown was fired and the team bought-out Brown's contract for $18 million. Brown walked away with a total of $28 million for coaching the Knicks for just one year.
After firing Larry Brown, Isiah Thomas assumed the duties of being the head coach of the Knicks. During a staged interview on MSG Network, which is the last time Dolan answered questions from the media, Dolan gave Thomas an ultimatum to show "evident progress" or potentially be fired. In the latter half of the 2006-2007 season, with the Knicks within reach of a playoff spot, Dolan signed Thomas to a multi-year contract extension. The team subsequently fell out of contention and Dolan was castigated in many quarters for his extension of Thomas' contract. The next season, Dolan stripped Thomas of his front office duties because Thomas had taken the Knicks to the playoffs just once during his tenure. New team President Donnie Walsh removed Thomas as head coach upon the conclusion of the season.
Other coaches that also had short-lived tenures as head coaches of the Knicks include Don Chaney (2001–2003) and Lenny Wilkens (2003–2005). Like Thomas and Brown, they remained on the Knicks' payroll following their departure from the bench due to multi-year contracts signed with the owner (and in Chaney's case, 2 separate contract extensions).
In 2007, Dolan was named as a defendant in a sexual harassment lawsuit submitted by a former Knicks executive, Anucha Browne-Sanders. Browne-Sanders accused Dolan of firing her out of spite after she complained about sexual harassment from Isiah Thomas. The court ruled in favor of Brown-Sanders and Dolan had to pay $3 million of the $11 million settlement. MSG was responsible for paying the remainder of the settlement.
In July 2012, Dolan faced criticism for allowing popular Knicks point guard Jeremy Lin to sign with the Houston Rockets without matching their $25.1 million offer.
In February 2015, Dolan responded to a letter from Irving Bierman, a 73-year-old, lifelong Knicks fan, that criticized Dolan's ownership of the Knicks and questioned his leadership with a seething letter of his own, telling the fan to "root for the Nets because the Knicks don't want you" and that Bierman was "a sad person" and probably an "alcoholic maybe"., Dolan later addressed the issue with the press, but did not apologize, only saying the letter was a case of "tit for tat" and declaring the incident "over"., Newly appointed NBA Commissioner Adam Silver did not reprimand or penalize Dolan, but instead further brushed the incident under the rug by calling Dolan a "consummate New Yorker” who received "an unkind email and responded with an unkind email”.,
On February 9, 2017, former Knicks player Charles Oakley was removed from Madison Square Garden during a Knicks–Clippers game following an altercation with MSG security. Oakley contends that Dolan has ignored, if not ostracized, him.
After winning the Stanley Cup in 1994, the Rangers saw a decline in performance in the wake of Dolan's increased role in managing the team and failed to make the playoffs from the 1997-1998 season until the 2004–05 NHL lockout, despite leading the league in payroll in most of those years. This was the longest playoff drought in the franchise's history, in part due to questionable, expensive free-agent signings, such as Eric Lindros, Pavel Bure, and Theo Fleury. Despite fan and media calls for the team's general manager Glen Sather to be fired for the organization's shortcomings, Sather was retained. However, since the resolution of the NHL lockout in 2005, Dolan has allowed Sather to rebuild from the ground up, which has led to a revival of the club and the organization, culminating with a trip to the Eastern Conference finals in 2012, their first since 1997. However, when Dolan spoke of the team's Stanley Cup chances in January 2012, Rangers head coach John Tortorella took issue with his remarks. "I have my owner up here talking about a Stanley Cup. That's a bunch of bullshit," Tortorella said in response. "We need to take it one game at a time."
On May 5, 2015 Dolan announced that Isiah Thomas would serve as president of the WNBA’s Liberty. Considering Thomas' history being both a failed President/GM of the Knicks and Thomas being implicated in the Anucha Browne-Sanders sexual harassment incident, it was questioned by many fans and members of the press.
Dolan rarely speaks with members of the media and communicates to the press through released statements or in interviews with MSG Network. In 2000, Dolan instituted media training for all Garden employees who might deal with the press and instituted an ironclad rule against team personnel criticizing others in the organization via the media. Under Dolan's watch MSG implemented controversial media policies limiting access to players. Some of these measures included prohibiting reporters and Knicks' beat writers from interviewing players without an MSG public relations official present, forbidding one-on-one interviews, and excommunicating writers who write articles critical of the organization. The policies also forbid the MSG Network from being critical of the Knicks and the Rangers, regardless of their performance. Such measures were not standard practice for other NBA teams. In addition, the Knicks did not make their medical staff available to the press. In 2004, longtime broadcaster Marv Albert's contract was not renewed by MSG Network, allegedly because of his criticism of the Knicks' play.