John Donovan gazed down at his belly: a bullet hole, blood. It was December 16, 2005, and John had a lot on his mind. It seemed that his entire life had been leading up to this moment: a Bay State legacy bolstered by a professorship at the Massachusetts Institute of Technology, a prodigious streak of entrepreneurship, and, more recently, the slow crumbling of his family’s dynastic ascent through Yankee upper-crust society.
As he sat in the front seat of his minivan—the vehicle hit by gunfire, blood pouring out of his abdomen—Donovan was in the midst of a vicious legal battle with his five grown children over the family estate, which included tens of millions of dollars’ worth of property in Massachusetts, Vermont, and Bermuda; even more millions of dollars in offshore accounts; and the blood-born trust between a father and his children that was supposed to hold the family name together. It was here, on this fateful night, in a dark parking garage outside Donovan’s Cambridge office, that the Donovan name would morph from a revered cornerstone of the Massachusetts aristocracy into an infamous badge, a tangle of letters best forgotten.
And yet Donovan, dialing 911 and placing his cellphone to his ear, didn’t know the depths to which his family name would sink in the coming years, the heights of bitterness to which the rivalry with his children would rise, or the lengths he would go to wrest control of the money that hung over his family like a cloud. All John Donovan knew at that moment was that he had a story to tell the dispatcher on the other end of the line. He claimed that his eldest son, James, had used his high-profile job at Goldman Sachs to launder $180 million—and now had sent two Russian assassins to kill him.
In that moment, John Donovan appeared to be the victim of a family spat that had become violent, but the truth—which has been laid bare in thousands of pages of court documents spanning nearly two decades—was quite the opposite.
Ensnarled in an acrimonious legal battle that has roiled Massachusetts high society, Donovan had set out to frame his eldest son for his attempted assassination. One of Massachusetts’s wealthiest families, the Donovans turned out to be less like the Kennedy ménage, on whom John tried to model his brood, and rather more like the fictional Roys of Succession , with a cunning business mogul engaging in a sordid feud with his children to keep all the power and riches that he had, ostensibly, earned for them all along. It was an act of betrayal so deep and depraved that its long-running narrative would climax, in May of this year, with the 80-year-old elder statesman of this once respected family sitting in a prison cell.
John Donovan grew up poor, an Irish kid on the gritty west side of Lynn, Massachusetts, who lived in a tenement apartment on the third floor and fended off bullies in the streets. But it was John’s academic precociousness that would elevate him out of poverty and into the ranks of Yale University, where he received a master’s degree both in science and engineering, as well as a PhD. It was a pedigree that would, alongside his entrepreneurial spirit, propel him into Boston’s upper class.
John’s rise began in 1966, when he started teaching electrical engineering and business at MIT. “His enthusiasm was infectious, and he made you feel like you were doing something really exciting and important,” Joe Alsop, who studied under Donovan and later founded a business with him before they parted ways, told me. “People are first enchanted by John, but then they encounter another, darker side.” (Donovan, through his lawyer, declined to comment for this article; a representative of the Donovan siblings did not respond to requests for comment.)
Around this time, Donovan started buying land in Hamilton, a North Shore enclave known for its equestrian estates and fox hunting. He eventually captured 600 acres in and around Hamilton—dubbing the properties, somewhat snobbily, Devon Glen, Seagate Smith’s Point, Willow Hill, and Sagamore—and his family became members of the uber-exclusive Myopia Hunt Club, which was founded in 1882 and counted some of Massachusetts’s most prestigious families as members. John wanted to be seen as a philanthropist, dreaming of one day donating large sums of money to Harvard, Yale, and MIT—a man remembered for giving back.
He garnered respect during his 15-year tenure at MIT, when he also wrote numerous books about computers, but Donovan made his wealth in the private sector. In 1977 he founded what would eventually evolve into Cambridge Technology Group (CTG), a company that provided consulting services to Fortune 500 companies, including Hewlett-Packard and Oracle, which paid John to upskill their executives through tech seminars.
His messaging, while informational, could seem almost cartoonishly cultlike. MIT professor Stuart Madnick, who founded CTG with Donovan before their own falling out, said that Donovan would hire a piano player to lead his students in song at the ends of seminars. “Every day with him was a unique experience,” Madnick says. In one training video from 1981 that he shared with me, Donovan steers a sailboat on the Charles River, a cluster of students perched adoringly at his feet. In another scene he welcomes his audience to Harvard and MIT, although his seminars were not officially affiliated with either institution. “He stretched things, in a way,” Madnick says. “He took liberties. But it clearly had a way of making connections with people.”
After he transformed himself from a campusbound computer geek into a traveling showman, the New York Times called him “the Johnny Carson of the executive training circuit,” and former Labor secretary Robert Reich once said that Donovan “has more ideas before lunch than most people have in a year—if ever.” In the 1990s Donovan told Steve Bailey, a longtime columnist for the Boston Globe who covered the Donovan saga extensively for more than 25 years and dubbed Donovan “the Nutty Professor,” that he could “tell the future.”
Donovan billed himself as the world’s foremost tech whisperer—he informally advised presidents Jimmy Carter, Ronald Reagan, and George H.W. Bush—and he founded more than a dozen other technology-adjacent companies. He cashed in when they were sold or went public, and he used the funds to expand both his business interests and real estate holdings. The Globe reported back in the ’90s that Donovan netted $15 million when Open Environment Corporation went public, in 1995; the business quickly nosedived after that. In 1996 Donovan raked in $6.5 million after OneWave Inc. had its IPO. That company too went belly up a year later.
Some questioned his methods. “When I started looking under the hood,” Bailey recently wrote in Boston magazine, “I found this self-proclaimed ‘visionary’ 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.”
As the years went on and his fortune grew, so did the myth of John Donovan. His reality, however, harbored dark secrets, and ruptures in his private life began to break through his public façade. John and his first wife, Marilyn—who was the mother of John’s five children—divorced in 1980. It was an acrimonious split, with Marilyn stating in a deposition, according to a 2004 Globe article, that John was “a cheat, a thief, in my opinion, a dishonest man, and in no way was a husband.” She moved to middle-class Danvers with the children, who attended Catholic school, and she landed a job at a local hospital. John tried to stay close with his kids, who were now entering high school. He brought them on vacations to Vermont and Windsor House, his Bermuda property, and had his eldest son, James, up to his 68-acre Hamilton estate to ride horses.
Donovan married his second wife, Mary Jo Bunker, whom he had met at one of his seminars, in 1984. Their union didn’t last long. They divorced in 1990, around the time Donovan started earning significant profits from his companies. “My husband’s conduct has become increasingly volatile and unpredictable,” Bunker wrote in divorce papers, according to Boston magazine. Bunker received a five-story Boston townhouse and $1 million as a settlement. In 1992 Donovan set up an offshore trust for his children, into which, over the next five years, he packed nearly $100 million worth of real estate and cash holdings.
Despite the massive bequest to his heirs, familial relationships began to deteriorate. If John were to tell it (as he did, in court documents), James stopped talking to him because he felt that John was favoring his youngest son, John Jr., whom John had hired as CTG’s chief operating officer. In James’s telling, he hadn’t spoken to his father in the years leading up to the start of their formal legal battle in 2002, as he, James, charted his own path in the world of high finance, working for Goldman Sachs and counting Mitt Romney as a client and close friend. (He would later advise President Donald Trump, who would nominate him for deputy treasury secretary.) John’s former business associate Joe Alsop once invited James to his house for a party. According to Alsop, James said, “I am Jim Donovan, but we are divorced,” referring to his father.
As for John’s three daughters—all successful in their own right, with Carolyn becoming a doctor and Maureen and Rebecca each earning an MBA—they stated in court documents that in 2002 they cut off contact with their father completely, a decision that stemmed from Maureen’s disclosure that John had molested her when she was a child. (John vehemently denied the allegations, saying through a spokesperson at the time, “I am terribly saddened by my daughter’s accusation, which I deny with all my heart.”) Maureen first divulged the abuse to Rebecca and James, and then to her mother and her other siblings at a subsequent family meeting. In a 2003 court filing, Maureen wrote, “The sexual abuse by my father has caused me tremendous pain, psychological trauma, and anguish, which continues to this day.” In her own affidavit, Carolyn wrote, “Her suffering was evident.” James told the court, unequivocally, “I believe my sister.”
Maureen’s revelation was certainly difficult for John Jr., who, out of the five children, was closest with their father. And yet, when his siblings needed him most, the youngest Donovan child came to their side. According to various court affidavits, on December 2, 2002, John Jr. called his father and said they needed to meet. John walked into the law offices of Mintz Levin in Boston to find John Jr., Rebecca, and their attorney. As they settled into the meeting, John Jr. told their father that one of the children had admitted to being abused and that they wanted a final separation, including that John abandon all his rights to any real estate owned by the family, including his current residence, Devon Glen, and even renounce his membership to the Myopia Hunt Club. “It was a very emotional time,” John Jr. later said in a deposition. “And I would prefer not to remember a lot of it, to be honest.” At one point John Jr. and his father stepped out into the hallway. “We’ve got to resolve this and move on,” John Jr. said, adding that his father had to understand prospect theory: that he had to make the right choice for the future, despite presently held biases.
John denied the abuse allegations, offered to submit to a lie detector test, and, according to his children, went around to prominent members of Boston’s North Shore community and claimed that his kin had fabricated the claims so they could assume his fortune. John, with the melodramatic flair that had come to define his salesmanship, would later claim in testimony, “I couldn’t even get out of bed, the betrayal was so great.”
The Donovans’ initial agreement, which gave the children complete control over the family’s real estate holdings in exchange for letting John live at Devon Glen, didn’t last. John reneged on the deal—claiming in court documents that he had been coerced into signing and accusing his children’s lawyer of threatening to leak the sexual abuse allegations to Bailey at the Globe . In 2003 the children sued John in Suffolk County Superior Court to enforce the agreement, commencing a vicious legal battle, motions for which are still being filed today.
Despite the escalation, John Jr., ever soft of heart, tried to hold his family together. He loaned his father $4.8 million so he could pay his other four children money owed under the settlement, and he tried to quell tensions between his father and his siblings. It didn’t work. John Jr. eventually asked the court to assign an arbitrator to oversee the dispute, with his lawyer writing, “[He] is not capable in his peacemaker role of resolving the serious conflicts that plague this family.”
The court appointed John S. Martin Jr., a retired judge, as the Donovan family arbitrator, but tensions continued to rise. By now John was convinced that James was the Oz behind the curtain, an evil conspirator who had turned John’s own children against him. After an especially contentious hearing, John allegedly told James, “You are a demon. You’ll be treated as a demon should be treated.” On another occasion John allegedly threatened to ruin him publicly, saying that James had young kids and a lot to lose. As the Wall Street Journal reported, according to a witness James allegedly said, “If I could kill my father and get away with it, I would.” (James, in court testimony, denied saying this.) Restraining orders reportedly were lobbed back and forth. The police were called. By 2005 the fight had turned into a war.
And the war turned bloody. On December 16, 2005, according to a court filing by prosecutors, John was served with questions relating to the abuse of Maureen, which he would have to answer during a deposition the following week. The hearing, however, would have to be delayed, because that night John was slumped over in the front seat of his minivan, feet sticking out the open door, a bullet having pierced his stomach. He miraculously survived a supposed assassination attempt at the hands of his eldest son. He dialed 911. “Who shot you?” the operator asked.
“It was a guy in a mask, a big guy. But he said… The other guy said James said he’d kill me.”
“Okay. James who?”
“What did [the man] say to you?”
“He said, ‘Motherfucker’s not dead,’ and shot me again.”
“Okay. That’s all he said?”
“No. He said, ‘There’s four more. We’ve got to get four more.’ He’s going to get four more.”
“Four more what?”
“Four more… I don’t… I think it’s four more people. He’s gonna get rid of the witnesses. He’s gonna get rid of the witnesses.”
“He laundered all the money through Goldman Sachs. James Donovan laundered the money, $180 million. He said he’d kill me.”
“And this is your brother?”
“Who is he?”
John didn’t answer the question—only continued to moan, pleading for help.
Details culled from the DA’s court filings lay out what prosecutors say happened over the preceding days, weeks, and months: After he was brought to Massachusetts General Hospital, Donovan’s story began to fall apart. Still bound to the stretcher, he dramatically coughed up a spent bullet fragment. The attending physician also found what looked like glass wedged deep in John’s right ear—the ear opposite the driver’s side window, which had been shot out. This seemed to defy the laws of physics. John told the doctor that he’d wager a beer that it was actually a bullet fragment.
Donovan’s bullet wound was also strange; Middlesex County prosecutors later noted that it was “consistent with someone grabbing a section of fat and the gun (bullet) going between those two points.” Although John had only one bullet wound, he told the doctors that he had been shot three times. A nurse checked out his metal belt buckle, which had a farm tractor on its face, and, sure enough, there were two bullet holes in it. While John was in the hospital, the police showed up at James’s house and, equipped with riot shields and submachine guns, searched it for nearly four hours.
Cambridge Police detective Rafael Beamud was tasked with finding out what the hell had happened to John Donovan. At the hospital Donovan told Beamud the same story he had told the 911 operator: His eldest son, James, had sent two Russian assassins to kill him so he could assume his fortune and cover up any misdeeds James had already committed. John, as he had done with the doctor, bet Beamud that the object in his ear was a bullet, wagering an authentic Irish dinner. “How the hell are you going to get a bullet in your ear?” Beamud asked me recently. “The guy was a work of art.” (The object, a piece of glass, was removed without incident.)
According to the prosecution’s filing, that night the Hamilton police, responding to an intrusion alarm at 8:06, 17 minutes before John’s 911 call, went to his home and found a number of knives strewn about the kitchen, which John claimed was further proof someone wanted him dead. (The police didn’t find any evidence of forced entry; a hardware store receipt for a spare key was found in his bedroom, leading the police to believe that a co-conspirator may have been involved.)
Beamud and two other officers visited Donovan at his home after he was released from the hospital; Donovan said that the assassins’ bullet casings had fallen into his shirt pocket, and that he had thrown them out of the car, which might explain why “they may all be in the same place.” Over the preceding few weeks, Donovan reported to Beamud continued strange happenings: Someone had put a listening device in his home, people were trying to break in, sketchy Russians were calling him.
The police, of course, had already checked out James Donovan. His alibi was airtight, his involvement seeming less likely as the investigation continued. Three months after the shooting, Beamud was convinced that John had staged his own attempted assassination. “We knew it was impossible that someone did this to him,” Beamud said in a recent interview. “There was only one other explanation: He did it to himself.” In March 2006 Beamud invited John to meet with him and Middlesex Assistant District Attorney Adrienne Lynch to talk through his story one last time.
According to a transcript put into evidence at trial, the conversation—pointed questions by Beamud and Lynch; long, rambling answers by John—veered far from the facts of the shooting, with John talking about his rags-to-riches background, his current business prospects (“I just got a wonderful contract with Citigroup—wonderful contract”), and his legacy as an entrepreneur (“I never really had a competitor in teaching [seminars]. It’s sort of, like, does, you know, Frank Sinatra have a competitor?”). He did say, however, that the Russian assassins used a silencer on their rifle, as if the incident had been plucked out of a John le Carré novel. “You could tell by his facial expressions that he knew he was getting caught in a lie,” Beamud told me.
The authorities uncovered a mountain of physical and forensic evidence that pointed to Donovan having staged his own shooting, including a to-do list, written on an Algonquin Club restaurant menu for the week of December 12, 2005 (veggie salad, seared scallops, spinach fettuccine with shrimp, and grilled veal chops) that included the bulleted words “face, mouth, belly, 8 shells, 4 in front, 4 outside, glass, gloves, rifle, fake happy,” and, most damningly, “glass gun? Where, shot where? Belt, coat.” According to news reports, it was also discovered that John had tampered with a security camera to redirect its view. “It’s a shame,” Beamud told me recently. “A professor at MIT? You wonder what’s going through his mind. Greed? Power? I have no idea. To stage an attempt on his life, to frame his own son: That’s crossing the line.”
In May 2006 the Middlesex district attorney’s office charged Donovan with filing a false police report and accused him of staging his own attempted assassination with the hope of framing his son. According to the Boston Globe , James, Maureen, Carolyn, and Rebecca released a statement that read, “We are saddened, but not surprised, by the actions of our estranged father referenced in the DA’s indictment,” while John Jr. released his own statement. “Despite all that has happened, I love my family,” he wrote. “This situation causes me tremendous pain every day. If I can help my father or my siblings through this, I will.”
It would take 15 months for John to go to trial; he was found guilty and sentenced to two years’ probation. “Mr. Donovan’s behavior can be described as nothing short of bizarre and premeditated,” the judge said. In another public statement about the case, the Donovan children wrote, “His bizarre allegations, including that this case involved ‘hundreds of millions of dollars,’ are as fictitious and phony as the one about Russians with rifles.” John continued to proclaim his innocence, telling the Globe after the verdict was announced, “I had nothing to do with the shooting.”
After being accused of hiring Russian hitmen to murder his father, James moved to Virginia. The war between John and his children, however, would continue, its wickedness increasing with every accusation lobbed by the Donovans in public and every plan hatched by John in private.
After his conviction, Donovan’s business prospects dried up. The 2008 financial crisis roiled markets, and his reputation was in ruins. Gone were the days of John Donovan, traveling showman, North Shore darling, the apple of the tech sector’s eye. He was now known only as the washed-up MIT professor who tried to frame his son by shooting himself in the stomach.
Around this time, John Jr. was diagnosed with a rare form of adrenal cancer, a terminal condition. Then John Sr. launched another scheme that, once exposed, would prompt the family’s arbitrator to conclude that John “apparently thinks the rest of us are devoid of intelligence or common sense,” a plan that “was so childish that even the least intelligent of us would never believe that what he was proposing was anything that [John Jr.] would have wanted.” In a 2016 deposition Donovan summarized his mindset during this time: “I was trying to get some sort of funding because I was flat broke.”
In 2013, according to court documents and depositions, Donovan began secretly recording conversations with his youngest son, who by then was slowly dying. In August 2013 John Jr. flew by helicopter from Manchester-by-the-Sea, where he lived (he also owned the Manchester Athletic Club), to Pomfret Mountain View, the family’s estate in Vermont, to meet with his father. Vermont had just legalized physician-assisted suicide, and John Jr. allegedly confided in his father that he was considering that option. John secretly recorded his son on this trip.
But John Jr. knew his father. So, before his death, he meticulously detailed his estate planning, including setting up a trust for his wife and children and pledging to sell a large portion of his property to the Trust for Public Land. He even recorded his wishes on videotape. “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,” he said, a breeze running through his hair, an American flag behind him. “I have not granted authority and do not want to grant authority to my father in particular in regard to their upbringing.” John Jr. also wrote an email to Judge Martin on April 24, 2015, reiterating these wishes, and even asked him to issue a permanent restraining order against his father. John Jr. died the following day. John Donovan was barred from attending the funeral.
In the weeks after John Jr.’s death, Donovan filed a flurry of documents with the Essex County registry of deeds, including a special power of attorney and a codicil of John Jr.’s will that essentially granted Donovan ownership of his youngest son’s estate and absolved him of the $4.8 million outstanding debt. Donovan also sent Martin a video. The onscreen heading read, “John Jr.’s Request to Judge Martin: After I Am Gone, Hear the Story in My Words.” It was an audio supercut, dubbed and spliced, of John’s secret recordings, edited together to give the impression that John Jr. wanted his father to oversee his estate.
The documents filed with the registry of deeds, unlike John’s secret recordings, were legally binding and had major chain-of-title implications for John Jr.’s multimillion-dollar estate. Martin held a series of hearings and, in a 2017 arbitration award, concluded that Donovan’s testimony “was a tissue of lies” and that all the documents he had filed were not only forgeries but also “a blatant attempt by Professor Donovan to defraud [John Jr.’s] estate.”
Martin also ruled that the deeds and will records filed by Donovan in the Essex County registry of deeds were null and void, and a Superior Court judge subsequently issued a final judgment affirming the arbitration award. (John has appealed the civil case’s most recent court order.)
“After I received the expungement notice, and when I started to read everything about John Donovan—when he got himself shot, or shot himself, or whatever—I said, ‘Wait, this guy is a con artist,’ ” Essex County register of deeds John O’Brien told me, adding that he reported the forgeries to the Essex County district attorney’s office. “I said, ‘You have to take a look at this. He did something criminally wrong.’ ”
Donovan was subsequently indicted on charges of forgery, thrusting him toward his second criminal trial in 10 years. (He was also sued by an investor of Send It Later—a company he had managed to become involved with even after he staged his own attempted murder—who accused him of embezzling company funds to support his lavish lifestyle, including $28,000 spent on the Hair Club for Men, according to one newspaper report. A judge awarded the investor $3 million in damages.)
All of this was especially bad timing for James, who had been offered the prestigious job of deputy treasury secretary by the Trump administration. After his father’s swindle was exposed in 2017, James backed out of the nomination. “I am deeply honored by President Trump’s decision to nominate me,” he wrote in a statement. “However, at this time I want to focus on my family, and I can no longer accept it.” (Three years later, after divorcing his wife, James would go on to reportedly date Trump’s former communications director Hope Hicks.)
It would take nearly five years for John Donovan to stand trial for scheming to swindle his dead son’s estate. He arrived at the courthouse this past May looking old and tired, his trademark gregariousness replaced by quiet despair. It was a remarkable turn of events for the once lauded prince of technology and multimillionaire MIT professor. Donovan was found guilty—he has appealed—and sentenced to two years in prison. “Mr. Donovan is 80 years old and undoubtedly contributed much to society,” Judge Salim Tabit said as the trial came to a close. “But for 20 years he has left a trail of tears everywhere he has been. It is my sincere hope that trail ends today.”
This story appears in the November 2022 issue of Town & Country. SUBSCRIBE NOW
Ian Frisch is a journalist and documentary producer who lives in Brooklyn; his first book is Magic is Dead: My Journey Into the World's Most Secretive Society of Magicians .