When I spoke with the entrepreneur Chris Whittle for the first time, this September, he was calling from his modest but tasteful saltbox home in Sharon, Connecticut, constructed in 1740. “It always amazes me that it was built before the revolution,” he tells me. “I really love it here.”
Whittle, now 77 years old, is often described as one of the great salesmen of his generation, so I’m not particularly surprised by his ability to make the best of a bad situation. He retreated to the $1.2 million house in 2023 to lick his wounds during the pandemic after losing nearly everything he had built for himself during the previous 40-plus years.
He remains extremely charming, dazzling even, which is another thing people often say about him. James B. Stewart, in a damning 1994 profile of Whittle for The New Yorker, wrote that Whittle’s charm may be his “most striking quality.” His longtime friend Rick Stengel, the former editor of Time magazine and a former deputy secretary of state, says he’s never seen Whittle raise his voice or be rude.
“Remember the Ronald Reagan line about optimists, of which he was one?,” Stengel asks me. “About the little boy who came down to Christmas morning and there’s a pile of manure under the tree, and he starts digging into it, and his father says, ‘Why are you doing that?’ He says, ‘There must be a pony in here somewhere.’ You know, Chris is a little like that.”
Whittle is mostly alone in Sharon these days. He’s divorced from photographer Priscilla Rattazzi, his wife of 32 years and a niece of Gianni Agnelli. (They have two grown daughters together.) Gone, too, are many of the totems of the wealth that he once enjoyed: his sprawling mansion, Briar Patch, on Georgica Pond, in East Hampton; a 15-acre farm in Vermont; the 10-room apartment in the Dakota that his friend the architect Peter Marino redesigned for him (it was Marino who introduced him to Rattazzi); a $12 million town house on East 91st Street, also renovated by Marino; and prime acreage on the Tennessee River, in Knoxville, near where he grew up. Whittle also had to jettison his two leased corporate private jets, his Porsche, and much of his art collection.
He no longer owns the over-the-top, four-story headquarters of his first venture, Whittle Communications, in Knoxville. The executive floor was referred to by other employees as “Versailles,” and the building is rumored to have cost his company almost $70 million. (It sat empty and unsold for years after Whittle abandoned it.) His New York office on Fifth Avenue is also closed, as is the one he had in the tony Seagram Building, on Park Avenue.
Along the way—and perhaps most painfully, apart from his divorce—Whittle fell out with his first business partner, Phillip Moffitt, and had a lifelong, up-and-down relationship with another one, the late Benno Schmidt. Schmidt left the presidency of Yale University in 1992 to join Whittle’s ambitious and disruptive Edison Project, a network of for-profit charter schools. And Moffitt, who was Whittle’s close friend at the University of Tennessee, joined him in buying and resurrecting Esquire magazine before selling it to its current owner, the Hearst Corporation.
In the face of life’s vicissitudes, though, Whittle’s charm remains undiminished. He may no longer wear his signature bow ties—an unusual accessory for an entrepreneur, but not for a Southern gentleman like himself—but he is unfailingly polite, candid, generous with his time, and patient, a man who readily acknowledges his failures but refuses to be bowed by them. “Let’s say it was a very hard chapter in my life,” he says.
School Ties
The H. Christopher Whittle saga started in Etowah, Tennessee, in the foothills of the Smoky Mountains. The son of a prominent doctor and a homemaker, Whittle became interested in journalism early. While he was in high school, he delivered newspapers and became a stringer for the local Etowah Enterprise and for the Knoxville and Chattanooga papers. He once described himself as “shy and too skinny” in high school, but he was popular enough to get elected student-body president.
He went on to attend the University of Tennessee, where he studied politics and was again elected president of the student government, this time with an education-reform campaign. A bumper sticker he made for the race read, For a Better Education, and he won by a large margin. “More kids voted that year than had ever voted,” he explains, “so it resonated.”
Whittle also began to pursue his interest in the media. He and some college friends started Knoxville in a Nutshell, a guide for their fellow students. Whittle met Moffitt and they became fast friends, deciding to expand Knoxville in a Nutshell to other college campuses and other topics. They named their company 13-30, for the age of the audience they were targeting. In December 1976, they sold an interest in 13-30 to the Bonnier Group, in Sweden, netting them several hundred thousand dollars each.
Whittle and Moffitt moved to New York to buy Esquire, which had been struggling financially. They turned it around and eventually sold it to Hearst, in 1986. That got Whittle his first financial windfall—estimated to be around $30 million—but cost him his friendship with Moffitt. Their interests were no longer aligned, and they went their separate ways. “It was not an easy parting,” Whittle told Stewart in the New Yorker profile. “It was hard fought.”
He went out on his own with Whittle Communications, a group of publications targeted at specific audiences, such as doctors and dentists, often with a single advertiser. He also conceived Channel One, a broadcast network devoted to students in public-school classrooms.
With each of his growing successes, he indulged his taste for the finer things in life—or, as Stewart put it, “his Medici impulses.” (Whittle is unapologetic about his spending during the time when he had more money.) In 1989, he sold half of Whittle Communications to Time Inc. for $185 million.
Instead of funneling his entire $40 million share of the proceeds back into his company, Whittle decided to make a big statement in East Hampton, buying an 11.25-acre 1931 estate on Briar Patch Road, with more than 13,000 square feet of living space and over 1,000 feet of water frontage on Georgica Pond. Whittle paid $7 million for the house, which was designed by the same architect who designed Jackie Kennedy’s childhood home in the Hamptons.
“People thought I was crazy,” he tells me. “Back then, that was regarded as slightly nuts.” But he and Rattazzi fell in love with the place and had to have it.
In 1992, he sold a 25 percent stake in Whittle Communications to Philips, the Dutch conglomerate that was a major supplier of television sets to Channel One, for another $175 million, valuing the company at around $700 million.
Not long after, Whittle Communications came crashing down. Whittle’s bankers put the screws to him for a $100 million–plus loan when the company did not hit its projections, and Channel One was sold off to an affiliate of KKR, the buyout firm, for $240 million. According to Stewart, Whittle Communications failed to pay state personal-property taxes on hundreds of thousands of television sets and videocassette recorders, used in Channel One classrooms, and failed to file some state-income-tax forms. Stewart wrote that Whittle Communications used “aggressive accounting practices” that resulted in “a significant overstatement of Channel One’s revenue” and had failed to pay an estimated $10 million in taxes.
“Based on everything I know, [the claims] are inaccurate,” Whittle told The Washington Post in 2019. (A point he reiterated with me and had also told Stewart.) Time Inc. wrote off the $185 million it paid for Whittle Communications, which later filed for bankruptcy and sold off its remaining assets.
He prefers to look on the bright side, though, telling me the original investors in Whittle Communications—family members as well as friends from the University of Tennessee—did extraordinarily well, making 99 times their money in that deal, after about 15 years. Time Inc., he concedes, got hosed.
But Whittle was not remotely done. Out of the ashes of Whittle Communications rose the Edison Project, which morphed into Edison Schools, an ambitious effort to build a national network of as many as 1,000 for-profit charter schools educating two million students. As part of the dissolution of Whittle Communications, the Edison Project was spun off to him—with part of the $40 million investment coming from none other than Philips Electronics. Whittle also received a payment of $7.5 million in exchange for a non-compete agreement.
“People thought I was crazy,” Whittle tells me. “Back then, that was regarded as slightly nuts.”
Whittle tells me he caught the education-reform bug when he was building a platform to run for governor of Tennessee. “I assumed that one day I would go into politics,” he said, and he came upon a new law, in Minnesota, creating charter schools. After some consideration, Whittle decided, “I would rather do charters on a national level than state-level politics, and I founded Edison.” He told Stewart that Edison would be “better than public life: A mission and free enterprise. A blend of capitalism and mission.” (Later, he also gave serious consideration to a run for a U.S. Senate seat in Tennessee before abandoning the effort.)
Whittle had big ambitions for Edison, whose first 200 schools would require as much as $3 billion in financing. He became the leading advocate for “whole-school reform,” an educational movement intent on remaking public schools from top to bottom. The idea, he says, was that “if you’re really going to change schools, you’ve got to look at them comprehensively, and you can’t tinker around the edges.”
The idea was controversial, especially among the entrenched public-school constituencies. Still, Whittle plowed ahead. “You have to have a West Berlin for East Berlin to fall,” he told The New York Times, “and what we’re really doing here is building West Berlin.”
He recruited big names to Edison Schools, including Schmidt—a huge catch, who was then the president of Yale University and former dean of Columbia Law School. Whittle was able to recruit to Edison seven of the eight educators he had hoped to be able to hire—the only holdout was Wendy Kopp, who went on to found Teach for America. More jets, fancy offices, and high salaries ensued. (Schmidt reportedly earned $800,000 a year.)
Soon enough, though, reality kicked in, and Whittle had to scale back his ambitions for Edison. In the end, over a 15-year period, Edison opened and ran about 133 charter schools—not 1,000—in 50 cities for some 60,000 students with a staff of more than 6,000. (He thinks about 95 of the schools are still operating. No small accomplishment.)
At an investor meeting, he recalls, he got asked about Edison’s competitors. He replied, “I’m sorry, sir, we don’t have competitors. We have enemies, and both unions at that time had full-time offices that whose job was to make my day a bad one.” He told The Washington Post that opening an Edison School was like “trying to do an elementary school on Omaha Beach.” Schmidt, who died in 2023, told the paper, “The frustrations and difficulties after 10 years or so just really added up.”
Once again, Whittle prefers to talk about the financial returns to his early investors. Sprout Group, the venture-capital arm of Donaldson, Lufkin & Jenrette—the first investment bank to go public, in 1970—invested $11 million in the initial round of financing for Edison and took out $200 million after seven years. “We were the second-best performer in that fund’s history,” he says. JPMorgan Chase & Co., Paul Allen, and the Wallenberg family fund, Investor AB, all invested, too. “They all made very significant money,” he says.
But by 1994, Edison was running out of funds. Whittle sold off some of his art and homes to come up with $15 million to entice a $12 million investment to Edison. Schmidt and two friends put in $3 million. Merrill Lynch took Edison public in November 1999, raising $122 million, at a valuation of around $750 million.
In early 2001, the Edison stock traded up to $38.75 a share, giving the company a market valuation of around $2 billion. If they got out, investors did well. Then Edison was hit by two unanticipated events: the bursting of the dot-com bubble and September 11.
Tom Ridge, then governor of Pennsylvania, had asked Edison to manage Philadelphia’s 250 public schools under the auspices of the state. Whittle agreed, but then Ridge left to become head of Homeland Security. Edison had lost its rabbi in Philadelphia. “I felt like it was the Bay of Pigs and we had no air cover,” Whittle tells me, “and the combination was not a good thing.”
The stock traded as low as 14 cents a share, after years of unprofitability, regulatory challenges, and much public opposition to the plan to have Edison take over the Philadelphia schools. Whittle, who owned about 14 percent of the company, stuck around and paid the price financially.
In 2003, Whittle, along with the private-equity firm Liberty Partners, arranged to take Edison Schools private for $1.76 a share. “This is a clear endorsement of Edison financially,” Whittle told The New York Times in 2003. He stayed for a few years and then left.
Whittle’s next project was Avenues: The World School, off the High Line, in Chelsea. It was another ambitious project, breaking into the stuffy, elitist world of Manhattan private schools. He took over a 215,000-square-foot former grocery warehouse and quickly turned it into one of the most successful new private schools in the city. Consultants told Whittle that the previous 10 private schools launched in New York City had a first-year enrollment of 52 students. By contrast, Avenues opened in September 2012 with 740 students spanning from pre-K to ninth grade. Tuition was $43,000 a year, and Whittle raised $100 million for the school.
Whittle again had a rough ride, though. He signed an NDA as part of his departure from Avenues, so he’s careful when discussing what happened. He was the largest shareholder of the school, which was privately held, but not the controlling shareholder. He describes what happened as “a hostile takeover,” where, in 2013, his private-equity partners decided to accept a bid for the company from John Fisher, the controversial heir to the Gap fortune and owner of the Oakland Athletics.
“I fought that and tried to do another bid,” Whittle says, “and I failed, and the party that bought the school outbid me.” A year ago, Nord Anglia Education, a London-based operator of 87 schools in 33 countries, bought the two Avenues schools. (A second Avenues opened in 2018, in São Paolo, Brazil).
But Avenues wasn’t what forced Whittle into his quasi-exile in the Sharon countryside. That distinction belongs to Whittle Schools & Studios, where he hoped to take what he was doing at Avenues to the next level. The company started in 2019, and the idea was to build major campuses, pre-K through 12th grade, in Washington, D.C., and Shenzhen, China, with additional schools to be built in Brooklyn and Suzhou, China, down the road.
Whittle hired architect Renzo Piano to design the school buildings, and The Washington Post was on hand when the D.C. location opened, in October 2019. It had been four years and some $900 million in the making and had an enrollment of 185 students. (Two days earlier, Whittle had been in Shenzhen for the opening of the school there.)
Then the coronavirus hit. “We were devastated,” he says. “All of our construction sites were closed. Our faculty couldn’t even get back into China during Covid. Our capital essentially declared ‘acts of God’ and said, ‘We’re not funding during Covid.’ It was a nightmare.”
Whittle Schools had written a $50 million check to Tishman Speyer, the New York developer, to start construction on the school in Brooklyn. But the project quickly ground to a halt, and Tishman Speyer took over the property and sold it to St. Francis College. In the fall of 2022, Whittle shut down the Washington campus right before the start of the new school year. He told The Washington Post that $100 million in funding was lost because of the pandemic and that he had taken out $30 million in loans and from investments to keep the school running.
In June 2022, the owners of the building housing the Washington school sued Whittle for allegedly failing to pay them $27.2 million in rent between April 2020 and May 2022. He said that at the same time the coronavirus hit, the Chinese government changed the way private schools in China were organized and funded, preventing the Whittle schools there from setting their own tuition in their own schools. The two Whittle schools in China remain open, taken over by their Chinese investors.
A Learning Experience
The dissolution of Whittle Schools was a disaster for Whittle on a personal level, too. He had put $25 million of his own money into the project—“Capital likes to see your capital alongside it,” he says.
The value of the house had increased exponentially over the years to something in the range of $100 million. “Up until I was about 45, I don’t think I had any debt,” he says. “[But then] I started using personal real estate investments [as collateral] … ,” he continues, “and usually that worked out really well, but not always.”
According to records found in various lawsuits involving Whittle and repayment of his loans, he borrowed $29.2 million, secured by the house, from Morgan Guaranty, in December 2001. He borrowed another $2 million, in December 2004, from Chase (which had bought J. P. Morgan), again secured by the house, and then another $8.25 million from the bank associated with Lehman Brothers, in November 2006. He tells me that these loans were all repaid or were refinanced without a problem.
“As the value of that property grew, I just used it,” he says, “and I placed mortgages on it for liquidity purposes and for whatever investments I was making.”
But Whittle’s personal financial problems began in earnest around the time Fisher took over Avenues. Whittle stayed on to help bring the school to China, and though he was earning $1 million a year—plus stock in the company and potential bonuses—he decided not to sell his stock as part of the sale to Fisher and instead obtained multiple loans from Avenues totaling $11.8 million. According to a 2018 legal complaint against Whittle by Avenues, the loans were secured by his stock in the school and were made to Whittle to “ameliorate his dire personal financial situation” so that he could focus on building Avenues.
Whittle resigned from Avenues, by e-mail, on January 21, 2015. The $11.8 million loan, which grew to almost $14 million with accrued interest, was due and payable in November 2018, and, according to the complaint, Whittle failed to make an interest payment that month. From there, Avenues not only alleged that Whittle had defaulted on the loan but violated a non-compete clause in his separation agreement by starting Whittle Schools.
On December 14, 2018, a New York court confirmed a judgment against Whittle, in Avenues’ favor, of $8.7 million. By July 2019, only $3.5 million of the judgment had been paid, and Avenues went after Whittle’s home in East Hampton to satisfy the balance of the outstanding judgment against him.
But there was another complication: the $25.4 million loan, also secured by the home, that Whittle used for his equity investment in Whittle Schools & Studios during a $170 million equity round. A Chinese company, Pure East Global Investments Limited, had made him the loan and was an investor in Whittle Schools, along with yet another Chinese company, Golden Eagle International Trading Limited, which also had Whittle’s East Hampton house as collateral.
Whittle now faced several creditors, each with a claim on his house: the two Chinese companies, in the senior position, and John Fisher, at Avenues, in a junior position.
After some jockeying between the Chinese and Fisher, a New York State judge ruled, in August 2022, in favor of the Chinese as the senior creditors, and, shortly thereafter, a court-appointed referee decided the home should be sold at auction. However, several private auctions for the home were rescheduled because nobody showed up to buy it. Finally, in July 2023, the Chinese took control of the house with a credit bid of nearly $85 million, the amount of two loans plus accrued interest, secured by the home.
In September 2024, Sotheby’s International Realty put the house back on the market for $95 million. It remains unsold. “It is a bargain,” Whittle says. “It’s priced to sell.”
In 2022, Whittle’s divorce from Rattazzi was finalized. “Strains in the couple’s 30-year marriage had also reached a breaking point,” The East Hampton Star reported in 2023. In her recent book of photographs, Three Lindens, about the trees at the Briar Patch estate, Rattazzi acknowledges Whittle “warmly,” according to the paper.
Meanwhile, Whittle defends his decision to use the house as collateral for his equity investment in Whittle Schools. “At the time that I did it, which was pre-Covid … I thought it was a good decision,” he says.
One successful private-equity investor tells me financial challenges come with the territory of being an entrepreneur. He says of Whittle, “People have ups and downs. It’s a view that he just didn’t have the discipline to grow and manage a business that had a clear and sustainable path to profitability. He wasn’t, ultimately, a great businessman. He was an innovative thinker.”
Somehow, Whittle has not lost his passion for trying to deliver a novel, quality educational experience for students. He’s now the executive chairman of Baret Scholars, a private global gap-year program with month-long study experiences in various regions of the world. Whittle wrote the program’s marketing materials and organized the speakers’ program for a recent stop in New York City. (Benno Schmidt also “played a pivotal role” in the creation of Baret before he died, in July 2023, shaping the content of the curriculum and scouting the program’s international locations. Despite the challenges he and Whittle faced working together at both Edison and Avenues, they remained more or less friendly until the end.)
But unlike with his other ventures, Whittle hasn’t put any of his own cash into Baret, although he is earning a monthly salary, and he’s still traveling around the world on Baret’s behalf. (Others have provided the necessary capital—largely investors from South America—to the tune of $12.5 million at a valuation of $35 million.) Instead, Whittle tells me, he’s one of the biggest individual shareholders, a stake he’s been given in exchange for his “sweat equity.”
In other words, Whittle is off to the races again. Asked to reflect on his roller-coaster career, he says that he doesn’t get enough credit for helping to spark a revolution in education. He says he’s created two “unicorns”—companies worth at least $1 billion, or nearly so—in his lifetime, with Edison and Whittle Communications, and wants people to know he’s a guy who gets things done, not just a dreamer in an ivory tower.
Whittle explains that he’s teaching a class to the Baret students titled Starting Things. Through his more than 50 years of entrepreneurial experience, he’s learned that there’s both art and physics involved in beginnings.
“I said to them, ‘You need to know that failure does not mean you have failed. It means that that time at bat failed and that, even though it may be painful to you, you will take a great deal from it and, in ways you may not know, it will inform and help the rest of your life.’”
Whittle was devastated by what happened to his career and his personal life but, he says, “I didn’t flinch in the sense of knowing what my skills and talents are.... It took me a couple years to recover from [what happened because] it was emotionally difficult as well.” But, as he’s been telling the Baret students to do, he’s picked himself up, dusted himself off, and is back at it again.
William D. Cohan is a Writer at Large at AIR MAIL and the author of such best-selling books as The Last Tycoons, House of Cards, and The Price of Silence. He is a founding partner of Puck. His latest book, Power Failure, is out now
