1장
The Man Who Shaped Entertainment: Lessons from a Hollywood Legend
When Jerry Weintraub passed away in 2015, George Clooney called him "our friend and leader and the legend we all hoped to become." Brad Pitt described him as "a legend, a friend, and a true original." From the Bronx streets to presidential palaces, Weintraub's extraordinary journey transformed entertainment forever. This son of a jewelry salesman built an empire by pure chutzpah, becoming the confidant of presidents, the producer of iconic films, and the revolutionary who changed how concerts were promoted worldwide. His memoir became an instant classic in entertainment circles, with Steven Soderbergh calling it required reading for anyone wanting to understand how Hollywood really works. Beyond the glitz and glamour lies a masterclass in relationship-building, problem-solving, and the art of the possible. As Weintraub himself would say, this isn't just a story about entertainment-it's about living life as if every day might be your greatest production.
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The Art of the Sell: Learning from a Master Showman
Growing up beneath the Jerome Avenue El in the Bronx, young Jerry Weintraub received his first education in promotion from his father Samuel, a jewelry salesman who understood the power of packaging and perception. Samuel's greatest lesson came through "The Star of Ardaban"-a worthless sapphire he transformed into a sensation by giving it an exotic name, displaying it with armed guards, generating press coverage, and ultimately donating it to the Smithsonian after using its notoriety to sell his entire jewelry collection to merchants across America.
This early lesson in creating value through storytelling became the foundation of Weintraub's career. When his father refused to buy him a coveted red James Dean jacket, insisting he earn it himself, Weintraub launched into entrepreneurship with remarkable ingenuity. Starting as a movie theater usher and resort busboy, he quickly graduated to creating his own delivery business at fourteen, managing a team of delivery boys handling everything from dry cleaning to groceries.
His talent for selling blossomed during his Air Force service in Alaska, where he recognized opportunity in the isolation of soldiers stationed near the Soviet border. While still in uniform, he worked at Sachs Men's Shop, creating a brilliant beach-themed window display to sell vacation packages to cold, lonely servicemen. He sold them everything-plane tickets, hotels, beach gear-"everything but the girl." This ability to sell dreams, not just products, would define his approach throughout his career.
Weintraub's promotional genius reached its peak with what he called his "P.T. Barnum tactics." He'd advertise "first come, first served" for Elvis shows as if that were newsworthy information. He claimed everything was a "limited edition" without specifying what the limits were. He understood that perception creates reality, and that enthusiasm is contagious. "I never feared trying crazy ideas to sell tickets," he explained. "The older men like Colonel Parker and Sinatra understood my P.T. Barnum ambitions, while my contemporaries dismissed me as nutty."
This willingness to think beyond conventional boundaries led to spectacular successes and occasional spectacular failures. Once, he attempted to organize an Elvis vs. Ricky Nelson softball game at Yankee Stadium-without actually knowing either star. The Yankees owner, Dan Topping, stood him at second base looking at all those empty seats, which became Weintraub's mental gauge for every future venture: could he fill that many seats?
3장
Building an Empire Through Relationships
Weintraub's extraordinary success wasn't built on talent or technical skills-he freely admitted he was "no actor" and couldn't type well enough to be a secretary. His empire was built on relationships, cultivated through genuine interest in people and an unwavering commitment to his word.
His marriage to singer Jane Morgan opened doors to a world of culture, languages, travel, and an elite network of celebrities and aristocrats. "Jane transformed my life," he acknowledged. "Suddenly producers and directors wanted to meet with me." This connection even led to friendship with George H.W. Bush, who became like family and included Weintraub in state dinners, White House stays, and private meetings with world leaders.
Weintraub understood that relationships required maintenance and reciprocity. When Frank Sinatra asked him to manage his comeback tour, Weintraub expressed concern about Sinatra's reputation for sometimes not showing up for performances. Sinatra's eyes turned icy, but then he pointed at Weintraub and said, "Here's what we're going to do. You and I are going to shake hands and promise. I'm never going to disappoint you. And you're never going to disappoint me, are you?" They shook on it, and neither ever broke that promise.
This emphasis on mutual trust extended to his business dealings. When Colonel Tom Parker surprised him by sharing merchandise profits after their first Elvis tour, he explained simply: "When I have a partner, I have a partner." Weintraub adopted this philosophy throughout his career, treating partnerships as sacred commitments rather than mere business arrangements.
Even in the cutthroat world of entertainment, Weintraub maintained relationships across decades. His friendship with the Colonel, though sometimes contentious, lasted until Parker's death in 1997, with Weintraub serving as a pallbearer and delivering a eulogy for his mentor. When Weintraub formed Management Three in 1963, he deliberately structured it as a partnership, explaining, "I have always been a believer in relationships, in strength in numbers and flying in a pack."
Perhaps most remarkably, Weintraub cultivated meaningful connections with people from all walks of life. From Mafia bosses who declared him their "nephew" under protection, to the Lubavitcher Rebbe whose spiritual guidance he sought, to presidents and world leaders who welcomed him into their inner circles-Weintraub's genuine interest in people transcended boundaries of class, religion, and status.
4장
Revolutionizing the Concert Business
Before Weintraub, the concert industry operated like a medieval fiefdom, divided into territories controlled by local promoters who made deals with venue operators, unions, and police. This system was inefficient and corrupt, with artists earning less than they deserved while various middlemen took their cuts.
Weintraub revolutionized this model, beginning with Elvis Presley's comeback tour. With Elvis's star power as leverage, he bypassed the traditional middlemen and booked directly with arenas. Rather than working on commission, he structured the tour as a production where Elvis, Colonel Parker, and Weintraub split profits as partners. This created economies of scale that increased profits for everyone involved-though it made Weintraub "the most hated man in the industry."
"Starting with Elvis," he explained, "we transformed the concert industry from regional fiefdoms to a national business. We cut out middlemen by partnering directly with artists and venue owners. As costs fell and profits rose, more artists sought me out, increasing my leverage to negotiate better deals, creating a virtuous cycle of growth."
This creative destruction meant the old promoters and operators got squeezed out. They resented Weintraub fiercely, with promoter Bill Graham telling Newsweek, "Jerry Weintraub comes into town like an eagle, scoops up the money, and leaves... He's more a power broker than a producer." Weintraub's unapologetic response? "Of course that's what I do-it's called business."
His key relationships shifted from promoters to arena owners-"wheelers and dealers, political players, sharpies and sharks interested in bricks and mortar, not art." One such figure was Arthur Wirtz, the six-foot-six giant who owned Chicago Stadium and most NHL franchises. When Weintraub tried to meet him about booking shows in his stadium, he learned he couldn't just call directly-in Chicago, everything went through Mayor Daley's machine, specifically Colonel Riley, a skinny Irishman with an eye patch who expected a bribe just to arrange a meeting.
When Weintraub finally got to Wirtz's office, he waited four hours while Wirtz sat alone signing checks. When Wirtz finally acknowledged him with a dismissive "What do you want?", Weintraub exploded: "Screw you!" To his surprise, Wirtz-this mountain of a man who controlled Chicago's arenas and commanded respect from gangsters to governors-laughed, walked around his desk, shook his hand, and they began a friendship that lasted decades.
After negotiating their deal, Wirtz staged a one-man "board meeting" to ratify it, teaching Weintraub an invaluable lesson: "Do it yourself. Don't ever go public. Be in charge of your own destiny." They made millions together through exclusive deals in hockey buildings nationwide.
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Creating Stars: The John Denver Story
Perhaps Weintraub's most impressive achievement in artist development was his work with John Denver, whom he essentially built from scratch. When Weintraub discovered him, Denver was playing to an empty Greenwich Village dive after leaving the Chad Mitchell Trio, making just $70 per show.
"John Denver would be my test case for everything I'd learned about selling and packaging," Weintraub explained. He started by creating buzz, talking Denver up incessantly around New York and LA until his friends begged him to stop. He embellished stories, claiming Bob Dylan was hanging out at John's shows every night. It worked-within weeks, Denver's venue was packed.
Denver had already recorded albums for RCA including "Rhymes and Reasons" and "Take Me to Tomorrow." His newest, "Poems, Prayers and Promises," contained an obvious hit: "Take Me Home, Country Roads." Weintraub's challenge was getting people to hear it. He sent Denver on a tour of major radio stations where he'd show up alone with his guitar and apple-pie face-perfectly timed for the early seventies when America was looking for trustworthy figures.
Rather than presenting Denver as an exciting new find, Weintraub sold him in the past tense-as someone already established that audiences had loved for years. He plastered Denver's face on every billboard from Bel Air to Hollywood. When people heard his songs, they already felt they knew him.
Weintraub even convinced RCA to release a greatest hits album when Denver only had one hit, securing a million-dollar deal-an enormous sum then. The album went straight to the top of the charts. They transitioned Denver to television, starting with appearances on The Tonight Show. When ABC initially signed him for five guest spots at $2,500 each, they used him once then canceled the contract. Four weeks later, when "Country Roads" hit, Weintraub signed a new deal with ABC for $350,000 per appearance.
Yet success brought its own challenges. Denver struggled with his identity and craved critical acclaim despite his massive commercial success. The relationship between artist and manager became strained as Denver sought independence from father figures. When Denver eventually fired Weintraub in a heated confrontation, his career declined-RCA and his agency dropped him, and he never regained his former prominence.
Years later, they finally reconciled when Denver explained he'd fired Weintraub because he needed to live without father figures controlling his life. Weintraub simply asked if he'd really done such a terrible job managing his career.
6장
Hollywood Transitions: From Music to Movies
By the late 1970s, Weintraub had an epiphany while looking at his daily call list-pages of people demanding his attention as a manager. He suddenly realized he didn't want to return any of these calls. The revelation wasn't about making calls, but about having to make them. He decided to quit the management business, telling his clients, "I love ya, find someone else, I'm done."
This freedom allowed him to transition fully into movie production, beginning with Robert Altman's groundbreaking film "Nashville" in 1975. Though he didn't understand the complex script with its million characters, he understood Altman's vision and put up his own money to get it started. He later sold TV rights to ABC before the film was made, bringing in Paramount as distributor. "Nashville" became a phenomenon that launched his producing career.
Weintraub entered Hollywood during a transition period-the old Hollywood of moguls who owned studios was fading, replaced by executives answerable to boards. The pioneers like Harry Cohn, Joseph Schenk, and Louis B. Mayer were giving way to a new corporate structure. Yet Weintraub brought the old-school showman's sensibility to this changing landscape.
As a producer, Weintraub saw himself as the driving force who finds stories worth filming, secures rights, hires writers for the crucial script, sets up studio deals, and oversees everything as the project's authority figure. "The job requires the right temperament," he explained, "enjoying the world, handling the politics of a movie set (that temporary city where I serve as mayor), and most importantly, solving problems."
His first major film production was "Oh, God!" starring George Burns. When Warner Bros. executives dismissed it as just "a nice little picture," Weintraub fought back. He demanded $5 million for TV marketing-unprecedented at the time-insisting "It's where John Denver's fans are." Though initially rejected, he convinced executives Terry Semel and Andy Fogelson, who put their careers on the line supporting him. The gamble paid off with packed theaters and box office success.
Other significant productions included "Diner" (1982), which launched careers for Ellen Barkin, Mickey Rourke, Kevin Bacon, Daniel Stern, and Steve Guttenberg, and "The Karate Kid," which originated from a news story about a bullied Valley kid who learned karate. Weintraub immediately saw potential in this Charles Atlas-like transformation tale, hiring screenwriter Robert Kamen and director John Avildsen. Finding Pat Morita for the role of Mr. Miyagi proved challenging until director Avildsen showed Weintraub a test video that moved him to tears. Morita's performance earned an Academy Award nomination.
7장
The Ocean's Trilogy: A Career Capstone
The Ocean's trilogy, which grossed over a billion dollars worldwide, became the capstone of Weintraub's remarkable career. Though he didn't produce the 1960 original starring the Rat Pack, he'd long wanted to remake it as the perfect showcase for young Hollywood stars who could match the original's wattage.
In 1998, he sent the script to director Steven Soderbergh and actor George Clooney, meeting them at the Smoke House restaurant in Burbank. The project's success hinged on assembling an incredible ensemble cast: George Clooney, Matt Damon, Brad Pitt, Julia Roberts, Andy Garcia, Elliott Gould, and Don Cheadle.
Making the Ocean's films was pure joy for Weintraub, often expressed through elaborate pranks-mostly aimed at him. Brad Pitt and George Clooney once challenged him to a vodka drinking contest on a flight from Europe. After fifteen shots Weintraub passed out, only to discover later they'd been drinking water while filling his clothes with thousands of M&Ms.
These friendships with Pitt, Clooney and Damon became as important to Weintraub as his earlier relationships with Sinatra and Elvis. "They're like my children," he reflected. "I learn from them, they learn from me, and developing true friendships later in life is one of life's greatest blessings."
The Ocean's trilogy represented a particular triumph because ensemble pictures had become nearly impossible to produce in an era when stars constantly compared their treatment. Yet Weintraub's decades of experience managing creative personalities-from his days at the Neighborhood Playhouse with James Caan and Dabney Coleman to his work with temperamental music stars-gave him the perfect skill set to navigate these complex dynamics.
The films also demonstrated Weintraub's remarkable ability to adapt to changing times. Having worked with the original Rat Pack generation, he understood the timeless appeal of charismatic stars joining forces, but updated the concept for contemporary audiences. As he observed, "Many claim Hollywood has lost its golden age glamour, but I've witnessed era after era and can tell you the stars now are exactly like the stars then. Only the clubs, styles and fashions have changed-the human drives remain constant."
8장
Life Lessons from a Master Showman
Throughout his extraordinary journey, Weintraub developed a philosophy of life and business that transcended the entertainment industry. These principles guided his decisions and shaped his remarkable success:
1. Tell the truth, even when it's uncomfortable. When Lew Wasserman caught him using the company WATS line for a three-hour personal call at MCA, Weintraub told him the truth instead of lying. This impressed Wasserman enough to mentor him. Years later, when his relationship with John Denver was deteriorating, he invented a fictional employee named Ferguson to absorb Denver's frustrations rather than allowing their partnership to collapse.
2. Listen when others speak. Weintraub's greatest skill wasn't talking but listening-truly hearing what people wanted and needed. This allowed him to connect Elvis with audiences, to understand what John Denver represented to Americans seeking authenticity, and to navigate the complex personalities of Hollywood stars.
3. Sell with joy and conviction. Whether promoting Elvis concerts, pitching "The Karate Kid" to studios, or convincing RCA to release a "greatest hits" album for an artist with only one hit, Weintraub approached selling not as manipulation but as sharing enthusiasm. His genuine excitement was contagious.
4. Never fear failure or looking silly. From attempting to organize an Elvis vs. Ricky Nelson softball game without knowing either star, to playing himself in "The Firm" alongside Tom Cruise and Gene Hackman despite his acting limitations, Weintraub embraced vulnerability and risk. As he put it, "I've always told the truth, listened when others spoke, sold with joy, and never feared failure or looking silly."
5. If you find something you love, keep doing it. After the failure of Weintraub Entertainment Group, which cost him $30 million and nearly ruined him, he learned a crucial lesson: running a studio took him away from what he loved-actually making movies. As his friend Steve Ross told him, "Companies always go away. They're a dime a dozen. It's talent that counts!" Weintraub soon returned to producing at Warner Bros., having learned that if you find something you love, keep doing it.
6. Know which calls to return. Perhaps his most profound realization came when he looked at his daily call sheet and decided he didn't want to return any of those calls. Unlike his friend Irving Azoff who had to return client calls, Weintraub could call back only who he wanted, when he wanted. This freedom-knowing which obligations truly matter-allowed him to focus on projects and relationships that brought him joy.
7. Recognize that life follows patterns whose author we cannot quite discern. Despite his remarkable success, Weintraub maintained profound humility, recognizing his life as a pattern whose author he could not fully understand. "The more I live," he reflected, "the more amazed I am by living." This spiritual dimension, deepened by his relationship with the Lubavitcher Rebbe, gave him perspective beyond material success.
Looking back on his extraordinary journey from the Bronx streets to Hollywood heights, Weintraub saw key moments that shaped his path-refusing the jewelry business, declining to wear tights in dance class, choosing not to return messages on call sheets. These seemingly small decisions created the trajectory of a remarkable life. Whatever lay ahead, he was determined to "rush to meet it with joy. This is, after all, a Jerry Weintraub Production."
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The Legacy of Relationships
What ultimately defined Weintraub's life wasn't his wealth or achievements but the extraordinary web of relationships he cultivated across decades. From presidents to mobsters, from Elvis to Clooney, from the Lubavitcher Rebbe to Armand Hammer, Weintraub connected with remarkable individuals who shaped the latter half of the twentieth century.
His friendship with Armand Hammer exemplified this talent for meaningful connection. Hammer-the son of a Communist who had known Lenin personally and later became CEO of Occidental Petroleum-saw in Weintraub a kindred spirit. They traveled together to China, where they were greeted on the tarmac by bands and diplomats, and to Moscow for Brezhnev's funeral, where Hammer somehow secured them seats with Castro, Qaddafi, and Arafat while American officials were relegated to back rows.
Weintraub's political connections transcended party lines. Though often described as a Republican powerbroker in liberal Hollywood, he valued friendship over politics. He worked with Jimmy Carter-"the most liberal politician I ever supported"-and later developed a close friendship with George H.W. Bush, who became like family and opened doors to a world Weintraub never could have accessed otherwise.
Even his family life reflected this capacity for complex, enduring relationships. When he fell in love with Susie Ekins in the 1990s, his wife Jane responded with remarkable wisdom. Instead of anger, she saw no reason for the legal complications of divorce when they could maintain their loving family bonds. Jane explained she wanted a quieter life painting while Weintraub needed someone fully engaged in his busy world. They told their children and grandchildren, who accepted the arrangement. "Jane and I remain deeply connected though living separately," he explained. "I've been with her for forty-eight years while building a life with Susie."
As Weintraub aged and friends began to die, his perspective on mortality evolved. "When your parents die, the wall between you and death collapses," he observed. He used to fear death intensely until visiting his dying friend Guy McElwaine, who smiled at his fear, saying, "It's just another journey." This made him confront his fears. "When more people who matter to you are gone than remain, the balance tilts toward the next world," he reflected. "I don't want to leave my beautiful life, but when God calls, I'll go without crying."
In his acknowledgments, Weintraub begins by recognizing how lucky he's been: "If there were true justice, I'd be saying thank you every moment from dawn till dusk." His extensive lists of actors, musicians, directors, and friends represent not just professional connections but a life spent at the center of entertainment-a testament to a man who understood that in business and in life, relationships are everything.
