It was the bar mitzvah that John Malone never thought he’d have.

The renowned cable mogul was feted Wednesday night by the UJA-Federation of New York, which bestowed on Malone its Steven J. Ross Humanitarian Award as part of its annual Leadership Awards dinner.

The event raised a record $2.5 million for the Jewish community service and philanthropy org as it brought out a who’s who of the cable and New York business community. Notables who came out to Cipriani 25 Broadway included Comcast’s Brian Roberts, IAC’s Barry Diller, DreamWorks’ Jeffrey Katzenberg, NBCUniversal’s Bonnie Hammer (last year’s recipient of the Ross kudo), AMC Networks’ Josh Sapan, Showtime’s Matt Blank, Merrill Lynch Bank of America’s Jessica Reif-Cohen and a full-court press of Malone lieutenants including Liberty Media CEO Greg Maffei, Discovery Communications CEO David Zaslav and Liberty Global CEO Mike Fries. Liontree Advisors Aryeh Bourkoff chaired the dinner with MediaLink’s Michael Kassan. A lengthy tribute video that screened during the presentation included testimonials about Malone’s genius and generosity from Ted Turner and Rupert Murdoch, along with a handful of youths who attended top private preparatory schools on scholarships provided by the Malone Family Foundation.

The timing of the dinner only magnified the aura of power that surrounds Malone. It fell on the same day that Charter Communications, the cable company in which Malone’s Liberty Broadband holds about a 25% stake, closed its hard-fought deal to acquire Time Warner Cable and Bright House Networks in a merger valued at $67.1 billion. One of the forces that Charter fought in its quest to buy TW Cable was Comcast. Roberts gave a heartfelt tribute to Malone as part of the proceedings and sat with Malone and his lieutenants at the power table. Roberts watched while Team Malone received a steady stream of congratulations on closing the deal — the deal that Roberts wanted badly for his own cable giant.

The crowd enjoyed the rare opportunity to hear from one of the architects of the pay TV eco-system through a candid “fireside chat” Q&A with media maven Charlie Rose. Rose probed Malone’s views on everything from the state of competition in TV (“the nightmare scenario for any businessman is that you have a rich, dumb competitor”) to his libertarian perspective on the presidential race (“you just shake your head — there are very real problems we have in our society and we worry about restrooms?”) to what keeps him up at night (“you gotta worry about everything”).

Rose elicited a candid response when he pressed Malone about whether he regretted selling his Tele-Communications Inc. empire to AT&T in 1999. “Looking back on it, was that a mistake? Hell yes,” Malone replied. “But that’s one that maybe I get to see it again” with the newly enlarged Charter, he said.

Comcast boss Roberts displayed a great sense of humor in his remarks on stage and a sporting demeanor throughout night.

“John, this is the Bar Mitzvah you never thought you were going to have,” he quipped. Roberts explained that the Jewish rite of passage for adolescent boys involves presents. “I’m giving you Time Warner Cable for your Bar Mitzvah,” Roberts said, to a big laugh from the crowd.

On a more serious note, Roberts and Malone exchanged the highest mogul-to-mogul compliments. Roberts called Malone his biggest mentor and role model after his own father, the late Comcast founder Ralph Roberts. Malone sounded like a father figure in telling Rose: “I’m so proud of Brian Roberts and what a fabulous job he’s done with Comcast.”

Diller also paid tribute to his longtime associate (and occasional sparring partner). “I’ve watched John Malone make Bill Gates cry, make Rupert Murdoch plead to get back control of his own company and Sumner (Redstone) get licked in court.”

Zaslav ran through the timeline of Malone’s career, including the fact that his first-ever programming investment was backing Robert Johnson in the creation of BET in 1979 and leading the cable biz bailout of Ted Turner in 1987 when Turner Broadcasting System was drowning in debt after buying MGM.

Outside of the business realm, Malone was saluted for the education-focused initiatives of the Malone Family Foundation and his pledge to preserve 2.2 million acres of land to be preserved “as open space forever.” (Malone is the nation’s largest individual landowner.)

When Malone was finally presented with his award, Malone said only “aw shucks” before sitting down with Rose, host of “CBS This Morning” PBS’ “Charlie Rose.”

Among the highlights from the conversation (which was held in front of a faux fireplace complete with a pile of logs):

  • On sage advice he received from one of his first bosses: “Always analyze the downside and structure everything so that you live to fight another day.”
  • On his preternatural focus on minimizing tax bills: “The government is your partner. They just don’t get to go to all your meetings. In the end, you can invest the money better than they can.”
  • On his proudest achievement: “After four years of really trying, I got my wife to say yes. It took me four years and that was four years of abstention, by the way. So it was really meaningful.”
  • On his greatest disappointment: “I let business take too large a part of my life for a period in my life and probably neglected the kids more than I should have.”
  • On the tug-of-war between cable and digital video purveyors: “It’s kind of poetic justice. The capital investments that our industry has made, not only domestically but internationally, have created the network capabilities that allow the Googles and the Apples and the Facebooks in particular to succeed. So we’re sort of part of that but we’re also threatened by it but we’re also driven by it.”
  • On the need for greater scale in traditional media companies: “We no longer can think of scale being sufficient if it’s just the U.S. When Mark Zuckerberg talks about a billion simultaneous daily users — those are big numbers.”
  • On the growth of original series production: “It’s like a children’s soccer match. Everybody in the industry is chasing the soccer ball instead of holding their position.”
  • On the fate of the cable bundle: “I don’t think the bundle will break down by itself. I think other bundles will build up. … The big bundle only breaks down if sports breaks down. That’s really the muscle. Sports is the glue that holds the bundle together. I don’t see that changing anytime soon.”
  • On Comcast’s acquisition of DreamWorks Animation: “I cheer that deal. Jeffrey (Katzenberg) had a great run but I think Brian (Roberts) can do more with the asset than Jeffrey. I love that. I like to see efficiency. I like to see good guys come out well.”
  • On his personal fortune (estimated by Forbes at $6.4 billion): “I couldn’t spend the money I’ve made if I lived 10 lifetimes. I’m going to give it away.”

(Pictured top: Charlie Rose, John Malone. Pictured below: David Zaslav, John Malone, Aryeh Bourkoff, Mike Fries)