The Last Days of Professor Donovan

Photo by Ken Yuszkus / Illustration by Benjamen Purvis

It was like a voice from the grave. Members of the jury in the trial of John Donovan—Boston’s notorious former tech guru turned convicted liar—watched a video of his son, John Donovan Jr., sitting outside on a brilliant New England day. The breeze ruffled his blond hair and an American flag reflected in the windowpane behind him. Eight months later, he would be dead.

That day, though, Donovan Jr. spoke deliberately, somberly into the camera. “Hi, I wanted to offer a very brief testimonial regarding the care of my children,” Donovan’s youngest son began. “If something were to happen to me, I want to be clear that my wife, Megan, is responsible for all decisions regarding my children and their upbringing. I have not granted authority and do not want to grant authority to my father in particular in regards to their upbringing…. And hopefully this won’t matter and won’t come to bear. But I thought it was important that I put this down in this testimonial for everyone to hear directly from me. Thank you.”

At the very end, Donovan Jr., the owner of the Manchester Athletic Club in Manchester-by-the-Sea, had one more piece of unfinished business: He sought a permanent restraining order preventing his father from having any contact with his wife and children. It was April, 24, 2015, and Donovan Jr. died of cancer the next day. He was 43 years old.

Donovan Jr. did not want to leave anything to chance—he knew his father too well. A smart Irish kid from a working-class neighborhood in West Lynn, the elder Donovan went to Yale and MIT, founded two dozen companies, wrote 20 books, and achieved considerable fame in business and academia. Along the way, he amassed a fortune and built a stellar reputation among his many big-name fans, including former U.S. Secretary of Labor Robert Reich. With each new success, he dreamed of building a family that stuck together. Etched in a stone on the hearth at his Manchester-by-the-Sea home were the words “Donovans stick together.” And he admired the loyalty espoused by another Irish family from Massachusetts: the Kennedys.

That never happened. Instead, Donovan has spent the past two decades in a ferocious legal battle with his five children, each chapter tawdrier than the last. In the most recent episode, he tried to cheat Donovan Jr.’s widow and children—Donovan’s own grandchildren—out of millions of dollars, their home, and other properties that Donovan Jr. bequeathed them. The Essex district attorney’s investigation found evidence that Donovan had forged 25 documents and doctored audio recordings that he’d surreptitiously made of Donovan Jr. while he was dying. As a result, the district attorney charged Donovan with a dozen crimes, including seven counts of forgery. After listening this past spring to the evidence against Donovan—including the video Donovan Jr. recorded before his death—a jury in Essex County Superior Court in Salem found Donovan guilty on all counts. In May, Judge Salim Tabit sentenced Donovan to two years and a day in state prison, followed by three years of probation.

Throughout the wild ride that has been Donovan’s life, right up until this latest installment, he had hungered for his family to be remembered. And it will be—just not as the family that stuck together, as Donovan had always hoped, but as the one he tore apart during what may be the longest-running, and certainly the most bizarre, family feud in recent Boston history. “Mr. Donovan is 80 years old and undoubtedly contributed much to society,” Judge Tabit said at the sentencing. “But for 20 years, he has left a trail of tears everywhere he has been. It is my sincere hope that trail ends today.”

As the longtime business editor and “Downtown” columnist for the Boston Globe, I spent more than a decade beginning in the mid-’90s writing about Donovan. He liked people to call him the Professor; I called him “the Nutty Professor.” He was a man who could launch a thousand columns.

Donovan was, in fact, a professor at MIT, and the New York Times dubbed him the “Johnny Carson of the training circuit” for his spell-binding, two-day corporate seminars touting the gospel of change. In those heady days, large companies such as AT & T and Samsung flocked to Cambridge to pay $300,000 to hear the Professor preach.

When I started looking under the hood, I found this self-proclaimed “visionary” (“I tell the future,” he once said) also had a habit of pushing little tech startups out into the then-red-hot IPO market, making him and other early investors rich, and the investors who followed poorer. That was a good business-page story; what would follow was much more.

Donovan had become wealthy from his seminars and his various startup companies. In the early 1990s, after a couple of contentious divorces, he set up trusts in his children’s names and transferred much of his money and real estate properties to them, even as he continued to occupy these properties. But the arrangement wouldn’t last: One of his daughters accused Donovan of sexually molesting her as a child. Her siblings rallied behind her and demanded their father vacate the properties owned by the trusts in their names. In effect, they filed for divorce from their dad, stating in court filings that they wanted nothing to do with him.

Donovan denied the allegation and then accused his kids of plundering the trusts—which his lawyers at the time said were worth more than $100 million. He also alleged his children had concocted the abuse charge to blackmail him. Then the story got even stranger.

On a December night in 2005, Donovan called 911 to report that he had been shot in a Cambridge parking lot by two Russian hitmen. He was saved, he said, by his belt buckle, which miraculously deflected the bullets, leaving him with only a flesh wound in the abdomen. Donovan told police he believed his oldest son, James, an investment banker for Goldman Sachs, had arranged the hit to appropriate his fortune.

You couldn’t make this stuff up—but, as it turned out, the Professor could. Twenty months after the alleged shooting, Donovan was charged with having made up the whole thing. After a bench trial, the judge convicted him of filing a false police report and sentenced him to two years of probation and community service. Among the evidence: Donovan had scrawled out the entire ruse on a menu from the swank Algonquin Club and inconveniently left it in his sport jacket. Calling Donovan’s behavior “bizarre and premeditated,” the judge ordered a psychiatric exam.

The scorched-earth campaign between the children and their father continued for years. They wrestled over luxe properties owned by the kids’ trusts in Manchester-by-the-Sea, Vermont, and Bermuda—the kinds of houses that have names such as Seagate, Pomfret Mountain View, and Winsor House. Repeatedly, Donovan and his children would settle the case, only for Donovan to hire new lawyers and challenge whatever he had agreed to.

Throughout it all, Donovan Jr. was the son who worked to mediate between his father and his siblings. He was sympathetic to the views of his brothers and sisters, but also remained concerned about the welfare of his father. He was instrumental in developing an agreement with his siblings to create a trust for their dad that they hoped would ensure his financial security for the rest of his life, and finally put an end to all the squabbling.

This latest—and apparently last—chapter in the Professor’s legal troubles began in 2016, when a local registrar of deeds in Salem became suspicious of 25 documents, including deeds, land transfers, and a will codicil, that were filed just as Donovan Jr.’s estate was being settled. These documents purported to show that Donovan Jr. had written a secret addition to his will and had given his father a special power of attorney to transfer assets from Donovan Jr.’s widow and children to Donovan and cancel millions of dollars in debts. In addition, Donovan secretly recorded conversations with his son and directed an employee from one of his startup companies, operating out of a barn at his home in Hamilton, to alter the video and audiotapes. The district attorney took up the case.

In Essex County Superior Court this spring, during a nearly four-week trial, Donovan looked like a shell of his former self. The man who built a fortune by casting a charismatic spell over investors and corporate chieftains, convincing them through his ample powers of persuasion that he could help their business, wasn’t wearing his tailored suits any longer. Instead, Donovan showed up every day wearing a green corduroy jacket and khaki pants, carrying his belongings in a fabric briefcase and a reusable shopping bag. In the end, he didn’t testify in his own defense.

It has been a long, downward slide for Donovan’s finances as well. Gone are the days of owning multiple properties spanning 1,000 acres, of being a philanthropist, and of being a member of the elite Myopia Hunt Club in Hamilton. These days, the most notable aspect of Donovan’s finances is his unpaid bills: almost $3 million in damages, interest, and attorneys’ fees that a judge ordered him to pay in 2020 after an investor in one of his failed companies sued him for spending investor money on personal expenses. In recent court filings, Donovan asked the government for assistance in preparing his defense. “He is indigent,” his lawyer, Robert Strasnick, told me.

Donovan pleaded not guilty to all charges related to Donovan Jr.’s estate. In his closing argument, Strasnick said that his client was a victim of a conspiracy by his children to maintain control over millions in assets and block an IRS investigation into payments from an offshore trust. Donovan Jr., the attorney said, was seeking to keep peace with his siblings and was working secretly with his father, first to donate or sell land to the Trust for Public Land, and later—as he was dying—to explore Vermont’s assisted-suicide law. The son had wanted the father to file the documents of his changed plans only after his death to avoid a conflict with his siblings, Strasnick said. The lawyer also claimed disgruntled former employees and the son of a former business associate played a role in setting up Donovan.

The jury, however, didn’t buy it, and the judge basically threw the book at Donovan, sending the Professor to state prison, not to clean brush from horse trails on the North Shore as community service, like the time he was convicted for faking the assassination attempt. (For unknown reasons, he never did do that community service, by the way.) Donovan Jr. “was the one person in the family who, despite his unresolved issues with his father, tried to maintain some semblance of a relationship with Mr. Donovan,” Judge Tabit said at Donovan’s sentencing. “This is what he got for his troubles: a man who waited for his son’s death to manipulate the system to attempt to steal from his son’s widow, and from his own grandchildren.”

It wasn’t until the day Donovan was sentenced that his current and third wife, Linda, appeared in the Salem courtroom, wearing black pants and a black-and-white-checked jacket. Through Donovan’s lawyer, she asked to address the judge in support of her husband. The judge did not allow it.

Donovan’s lawyer claimed Donovan was indigent and that Donovan had to borrow money to support Linda, yet Linda is far from slumming it. She lives quite comfortably 1,000 miles from Boston in Aiken, South Carolina, horse country for the rich. She spends most of her time in “the Winter Colony,” as the wealthy northerners like to call it—a picture-postcard town of 30,000. It has a famed history as a sportsman’s paradise for polo, fox hunting, carriage riding, and show jumping, with world-class training facilities. A highlight of the season is the annual Blessing of the Hounds on Thanksgiving.

Since 2015, Linda has lived on a 40-acre farm previously owned by the Duchossois family, a wealthy Chicago clan. (The farm was bought for $1 million by a trust overseen by the former judge arbitrating the decades-long legal battle between Donovan and his children over the trusts.) She lives behind the gates with her horses, dogs, and peacocks. An old real estate listing describes her home as a “first-class equestrian center” with 16 stalls for the horses. “She is living the life of a 12-year-old who always wanted a pony. That is the life she always says she is living,’’ says an acquaintance, who like Linda fled the horse life of Massachusetts’ North Shore for the Winter Colony. She describes Linda as “quiet, demure, and likable,” living simply and unpretentiously, alone except for her animals. Linda didn’t reply to my efforts to reach her by phone, text, and email.

None of Donovan’s children would speak with me either, but there’s a lot you can glean about the eldest son James’s current life from following the news. James was the Goldman Sachs banker his father accused of sending Russian hitmen to kill him. More recently, he was in line to become the second in command in Donald Trump’s Treasury Department in 2017, but withdrew citing family concerns. Two years later, he filed for divorce from his longtime wife. A year after that, he turned up in the tabloids as the new boyfriend of Hope Hicks, Trump’s former communications director.

One thing that hasn’t changed in the Donovan family is its patriarch’s ability to concoct tales. At the sentencing hearing, the prosecutor said he was offended to read that Donovan’s lawyer claimed his client was honorably discharged from the U.S. Air Force given that years earlier, Donovan himself had said—under oath—that he never made it through ROTC.

Then there were his attempts to rewrite history a year after Donovan Jr.’s death. Donovan self-published a self-pitying book titled Make the Moments Better: Life Rules for Business and Family. The book “is a roadmap for being more successful in your business, in your family, and in your personal relationships,” the jacket says. “There are tremendous highs and lows in life, and having the ability to navigate these with grace and dignity will make the moments in your life better, and it will do the same for those around you.” Donovan slapped his son’s name on the cover as a co-author and dedicated it to him. The son’s widow objected to the book, and the court-appointed arbitrator ordered it taken off the Internet.

It’s a book that should come with a warning label: Through 233 pages and 100 life lessons, Donovan never gets around to the faux hitmen, his daughter’s allegation of sexual abuse, nor the two decades of internecine court battles with his family. The closest he comes is lesson number 95, on reputation: “One would think that a solid reputation would be impervious, especially mine—a tenured professor at several universities, established 26 companies, advisor to three presidents, never even a traffic infraction. Never an accusation of any impropriety in fifty years. However, my reputation was ruined.”

My personal favorite, though, is lesson number 91: “Always choose a jury trial.” In the end, Donovan’s recent jury trial worked out even worse for him than his bench trial for faking an assassination hit.

Years ago, Donovan sat with me and tried to explain why so many people had so many awful things to say about him. He can spin a yarn, and as we talked, he kept returning to Barrett Street in West Lynn, where he grew up in a third-floor tenement apartment. It was a place where the bullies were constantly out to get him and his brother, Paul. “These kids used to jump out and really lay on us from these alleys,” he told me. So it has been through his life: The bullies, he said, are still after him. “If you look back at my life, it’s been kids coming out to get me.” Over the past 20 years, though, the kids he has been battling are the ones who know him best: his own children. And all they have wanted is to get away from their father.

It looks like they have finally gotten their wish. The once-bullied boy turned bully of a father will not be able to harm them anymore. At the end of his sentencing, Donovan, whose hair looked dirty and unkempt and who had thick stubble on his face, clutched his jacket to his chest and a roll of toilet paper in his hands as he shuffled off to prison.

To learn more about the reporting of this piece, check out this interview with writer Steve Bailey.