College of the Holy Spook

As promised in the Thursday edition, here’s an essay I’ve been working on about Holy Cross and the CIA. It’s pretty neat stuff—interesting to think about given that both institutions still exist. 

I scheduled this post on Thursday afternoon, and I’m currently in the woods in Maine. So if anything big happened on Friday or Saturday, I won’t even know about it until tomorrow! 

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The other night I was watching Mafia Spies, a new docuseries about the CIA’s many attempts to assassinate Fidel Castro in the 1960s. Some 45 minutes into the first episode, I stumbled across maybe the most insane “there’s always a Worcester connection” moment of all time: Robert Maheu, a Holy Cross graduate turned FBI agent turned private investigator, who, among many many other things, brokered a deal between the CIA and the mafia to try to take out Fidel. 

That’s right, folks: the key figure in one of America’s wildest actually true conspiracies was a Crusader. You love to see it. 

The way the Mafia Spies narrator puts it, the CIA was looking for an interlocutor that was at the same time sketchy enough and trustworthy enough to meet with the mob on their behalf. Richard Bissell, a CIA higherup, suggested Maheu.

Maheu, a “good Catholic boy who went to Holy Cross,” was conflicted at first, the narrator said, but Bissell won him over with a claim of patriotism. Maheu apparently agreed to the assignment on the rationale that he would have assassinated Hitler if he had the chance, and in his imagination, Castro=Hitler.  

Mahue, our sweet little Catholic boy, had a meeting with Johnny Roselli, a Hollywood-based mobster working for the Chicago Outfit. And the rest is history! Deeply, deeply guarded history. The full extent of which we’re just beginning to understand. And a product of our very own College of the Holy Cross was an integral part of it. Amazing. As we’ll get to later, he wasn’t the only one! In fact there’s a much more powerful and central CIA figure with ties to both Maheu and Holy Cross, as I came to learn in following this little rabbit hole. One who never seems to get mentioned when relitigating the activities of The Agency. Hm!

Since August is a slow month for news and I find this stuff personally interesting, I spent a lot of time over the past week prying into the connection between Holy Cross and the CIA. The following is based on both the Mafia Spies 2024 documentary and 2018 book, as well as multiple biographies, internal CIA and FBI documents, and newspaper archives. Fun stuff! Provided to you for the purpose of fun Worcester connections—until, that is, you get to the end, where there’s a particular Worcester connection which might bend your reality, as it did mine.

First, a look at how Maheu went from our glimmering college on the hill down into the depths of the deep state. 

Born in Waterville, Maine to working class parents, Maheu got a partial scholarship to Holy Cross. In his memoir, he describes his time there this way

Holy Cross is located in Worcester, Massachusetts, a tranquil college town in the center of the state. It’s curious, but even though we were in the midst of a depression—and building toward war—my years at Holy Cross were idyllic. Oh, I had to work, all right, waiting on tables. But I never minded that. Most of my time was spent in study and discussion, two endeavors that I’ve always loved. I even found time to join the debating team, and to become its president. One of my closest friends on the team was a young fellow named Edward Bennett Williams. Years later, he would head his own powerful Washington law firm and become extremely influential in Washington. He would also change my life by opening the door to the man who would be my most important client—Howard Hughes.

Edward Bennett Williams is… interesting. A high powered Washington attorney, the list of clients he’s represented is a veritable who’s who of CIA conspiracies: Jack Ruby, Sam Giancana, Richard Helms, Sun Myung Moon, John Hinckley, Jr., Jimmy Hoffa, Frank Sinatra… etc. etc. Safe to say, I think, that Williams was spooked up. And here we have a close friend of his from college brokering a deal between the CIA and the mob. 

So after developing a close relationship with the #1 Spook Lawyer, Maheu graduated in 1940 and wouldn’t you know it, he got a job at the FBI right out of college—through another Holy Cross friend named Jack Delaney. 

Mahue worked at the FBI for seven years, sniffing out German sympathizers and rounding up Japanese Americans for the internment camps. In 1947, he resigned, then opened a private investigator practice, and his main client quickly became the CIA.

“The CIA was my first steady client, giving me ‘cut-out’ assignments (those jobs in which the agency could not officially be involved),” Maheu admitted late in life.  

The Castro assassination plot is far from the only sketchy operation Maheu had his fingerprints on over a long career of ‘cut out assignments.’ A 12-page CIA dossier in the JFK files, written in 1975 but released in 2018 with heavy redactions, paints a picture of a morally agnostic fixer. A CIA official describes him as “a covert asset who could be utilized by the Office in extremely sensitive cases.”

In 1954, he worked on a project to scrap a Saudi oil deal with one Aristotle Onassis. 

The same year, he was about to be charged under the Mann Act due to “procuring and transporting prostitutes for (REDACTED) during (REDACTED)” but it got uhhh taken care of… 

Who took care of it? Fellow Crusader Edward Bennett Williams. Talk about “inner circle.” 

In 1957, he filmed a fake sex tape of Indonesian President Sukarno, intending to distribute it around Southeast Asia to hurt his reputation. The project, known as Happy Days, was mostly shelved. The CIA released a small portion of it years later, according to the Mafia Spies book. 

And then there’s this incredibly vague incursion into the “international labor” movement.

In 1960, he did the pre-Bay of Pigs Castro stuff we’ve already gone over, meeting with mobster Johnny Roselli on behalf of the CIA. Interestingly, though, it wasn’t the first time the two had met. A few years earlier, he asked for Roselli’s help getting a room in an overbooked Las Vegas hotel. It worked. “Magically, the doors opened up,” according to the book Mafia Spies, on which the docuseries is based. Who brokered that initial meeting? Edward Bennett Williams. Hm!

In the 1970s, Maheu got into the South America game. 

Oh and also his son was CIA as well.

Project QKENCHANT is about getting officially non-CIA actors, like Maheu (and Williams?), official security clearances. 

And he is maybe kinda sorta the go-between for Howard Huges and the CIA to “work out an arrangement whereby he or his organization could become a front for the CIA.”

On the CIA’s own website, they brag openly about one such instance: Project Azorian:

In 1974, CIA built a ship called the Glomar Explorer to secretly snatch a wrecked Soviet submarine from the bottom of the Pacific Ocean.

The cover story was that billionaire Howard Hughes was conducting marine research at extreme ocean depths and mining manganese nodules lying on the sea bottom. However, news reports on March 18, 1975 exposed the Glomar Explorer and its secret mission.

This is what the ship looked like:

Insane. All thanks to our good Holy Cross boy. 

Even more insane: Maheu might have been the inspiration for the Mission Impossible television series, at least according to Jim Hougan, author of Spooks. 

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Our other good Holy Cross boy, Edward Bennett Williams, never worked as a CIA agent per se. Not in the way Maheu did. The Mission Impossible way. At least as far as we know. 

Questions aside, his known involvement with the CIA was a lot more consequential than any one agent’s could ever hope to be.  As a trial lawyer, he just so happened to represent the defendants which made the CIA most uncomfortable, and he almost always got them off and further questioning suppressed. Some of these clients were powerful figures in organized crime, like Frank Costello, Sam Giancana, and Jimmy Hoffa. Williams’ FBI file is more than 600 pages long.  At the same time, he informally advised presidents on how to handle scandals like Watergate and the Iran Contra affair. They took his advice. He was so important, two presidents offered him the CIA directorship (he declined it both times). When looking for a link between the intelligence community and the mob, Williams would be a great place to start, and yet I couldn’t find an example of any researcher starting there. (For instance: He’s not mentioned once in the Mafia Spies documentary and only racks three cursory mentions in the book.) Hm! 

Before either got involved with the CIA, Williams and Maheu became friends on the Holy Cross debate team. The friendship would carry on for years and years. 

Early in both of their careers, the pair went on an adventure to Italy to exonerate the OSS (proto-CIA) spy Aldo Icardi of the murder of a fellow covert operator Bill Holohan. In Williams’ biography, The Man To See, author Evan Thomas puts it this way:

Williams was touched by Icardi’s plight and wanted to help. He could also see the potential for a headline-grabbing trial. He asked Icardi for $1,000 so he could go to Italy and investigate the case. Then he called his old Holy Cross debating partner Robert Maheu and asked him if he wanted “to go on a really exciting trip.” A former FBI agent, Maheu had formed his own private detective agency. (Although Williams did not know it at the time, Maheu was also on the payroll of the CIA.) 

Citation needed! Whether Williams knew at this time about Maheu’s involvement as a CIA cutout man is, to my mind, a very open question. I mean c’mon. Of course he knew. 

The pair flew to Rome and began interviewing “partisans” who may have known  something about Holohan’s death. They stuffed a recorder into a briefcase and met a local communist figure, Vincenzo Moscatelli, who, they say, confessed to ordering the murder. Though inadmissible evidence, Williams used the briefcase recording sneakily to get Icardi off the murder charges. (Icardi would later go on to write a memoir, calling himself a “master spy.”)

This being a fanciful trip by a couple rogues really stretches credulity—especially given all we’ve come to learn about the Operation Gladio activities going on in Italy at the time. The stay-behind units and the deliberate sabotaging of communist organizing and the compacts made between the Vatican, the mob, and U.S. intelligence (good breakdown of that in Matt Christman’s “The Inebriated Past” series). Reading this escapade in that light—as the work of two cutout men—makes a lot more sense.

A few years later, when a U-2 spy plane was shot down over the Soviet Union and U.S. pilot Francis Gary Powers was taken prisoner, Williams got the case: 

This was the great age of spy versus spy in the Cold War, and Williams, a staunch anti-Communist, wanted to join the game. He loved secrets; he loved knowing what others could not, and he understood that information was power in Washington. Williams was intrigued by the secret life of his friend Robert Maheu, a private investigator who performed “off the books” operations for the CIA. So when the U-2 spy plane of Francis Gary Powers was shot down over the Soviet Union and Powers was taken prisoner, Williams approached the State Department in January 1960 to see if he could serve as Powers’s lawyer.

Later that year, a CIA agent found Williams roaming the halls of the agency’s headquarters. Apparently, he was there upon return from a trip to the Philippines, where he was “checking out one of his clients.” An American businessman, unnamed in the biography, may have been involved in the communist insurrection there. Williams went to investigate, then was debriefed by then-director Allan Dulles himself. Who does all that? Who gets debriefed by the director of the CIA after going to Manilla to investigate communistic activities? A spook.  That’s who. 

For some reason, the author of this autobiography maintains all this involvement with The Agency was due to some romantic boyhood enthusiasm in spycraft. Nowhere within is the idea that Williams was in fact an asset. Simply not interrogated. Against all the evidence within it! Stuff like this: 

“Williams could not have been more cooperative,” (CIA General Counsel Lawrence) Houston recalled. “He had a keen sense of intelligence and secrecy.”

Hm!

He represented Sam Giancana, a Mafia boss involved in the CIA plot to assassinate Castro, when the feds were building a case against him. Williams went straight to a guy at the Department of Justice named Bill Hundley, had a chat, and the matter disappeared. 

“Whatever Williams told Hundley, it was enough.” 

He represented a Green Beret named Robert Rheault, charged for the brutal execution of a South Vietnamese double agent. He got him off by privately applying pressure on the Justice Department:

The Green Beret would have to testify as well that he had participated in illegal cross-border operations into Cambodia. The White House would choke on these disclosures, Williams predicted, and drop the case.

The feds dropped the case. Hm!

In 1975, the CIA was under fire in a post-Watergate era, and who was there to advise President Gerald Ford on how to handle it? Edward Bennett Williams. 

At the White House, Ford listened to the baying and worried about the future of the CIA. Congressmen were talking about creating a special committee to probe the Agency. With columnists inveighing against the “Imperial Presidency,” the balance of power was swinging back to Capitol Hill. What should the president do? Ford asked Ed Williams. Appoint your own commission, Williams answered. Get ahead of the curve. Ford responded by creating the Rockefeller Commission, under his vice president, Nelson Rockefeller, to propose reforms in the intelligence community. The commission was not able to entirely dull the sting of congressional investigations, but at least it showed that the White House was not on the defensive.

Then, Ford asked Williams to become the director of the CIA. He declined,  in part because he “didn’t want to get caught doing anything illegal.” And a public-facing position is, of course, hotter than the one he had as a man-about-town trial lawyer. 

The job went instead to George W. Bush. Williams was the first choice for CIA director over Poppy Bush. He declined it as one would a lateral move that comes with some mild personal inconveniences.

Instead, he joined the Foreign Intelligence Advisory Board, a commission Ford created to show the public that the CIA was being monitored. 

Williams was pleased to be put in the company of these men, and even happier to be made privy to the deepest secrets of all, the most highly classified operations of the intelligence agencies.

Hard to believe he was not already privy, as this bit of editorializing by the hagiographer suggests. 

In this advisory capacity, Williams successfully lobbied to increase the CIA and NSA’s ability to wiretap U.S. citizens. Hm!

When former CIA director Richard Helms got in trouble in 1976 for an off-the-books CIA breakin, Williams told him he’d personally defend him in court. He did, arguing national security made it “perfectly permissible for the Agency to do what the police could not do to solve ordinary crimes.” That worked. Helms got off! Williams represented him pro bono, refusing to take his money. Hm!

Williams was also close with William Casey, another CIA director:

Casey preferred this nonbureaucratic approach to problem solving. Williams was the CIA director’s own “off-the-shelf’ legal troubleshooter.

The author suggests that “suspicion arises” that Casey used Williams for more than that. Did Casey tell Williams about Iran Contra, for instance? Well, Richard Helms said no. So that’s where the biographer leaves it. I’m gunna go ahead and say, emphatically: of course he fuckin’ knew about Iran Contra. 

When news of it broke, and Oliver North was facing charges, Williams would have represented him, but it was too messy, given how close he was to all of it: 

The players in Iran-contra were all familiar names in Williams’s Rolodex. Williams was a close friend of the lawyer chosen by the Senate to lead the Iran-contra investigation, Arthur Liman. At the time, Liman was Williams’s co-counsel in the defense of junk bond king Michael Milken. Williams represented the Washington Post, a newspaper with a score of reporters devoted to uncovering the secret acts of Williams’s friend, Bill Casey, and the firm’s client, Oliver North. To make matters even more incestuous, Williams was an old and useful source to the Post’s top investigative reporter, Bob Woodward.

So instead, Williams’ protege Brendan Sullivan represented North and, of course, got him off. 

The second time Williams turned down the CIA director post was when Ronald Reagan asked, and it was for health reasons. 

So in conclusion, I think it’s safe to say that Maheu might have been the stereotypical spy, but Williams was the real CIA operative of this Holy Cross pair. Curiously, Bennett’s name doesn’t get invoked the way Maheu’s does when it comes to CIA conspiracy theories, but then again, the big dog doesn’t have to bark as much. That doesn’t mean Williams was any less involved—in fact, quite the opposite.

Just two good Catholic boys getting a decent education in our city Worcester MA then going on to facilitate the most shadowy and brutal excesses of an evil, paranoid empire that is still destroying the world. Always a Worcester connection! We love it. 

Back to the local angle, Maheu all but disappeared after his Holy Cross days, but Williams continues to loom large. 

Williams was on the Holy Cross board for years, up until he died. As chair for most of his tenure, he raised millions for the institution.  He also got pissy about little things: “It bothered Williams that a college building facing the street had unsightly air conditioners sticking out of the window,” his biography reads.  He demanded that they be removed. 

Williams was a prolific letter of recommendation writer for both Georgetown and Holy Cross. His recommendation meant the recipient would be accepted—when he wanted them to be. He had an explicit agreement with both schools: “If he sent a handwritten note, it meant admit; if he sent this form letter, ignore it.”

An interesting gaff: In 1985, he had the mayor of Philly, Wilson Goode, come speak at the Holy Cross graduation. Only problem, it was a couple weeks after Philly police sought to eradicate MOVE and firebombed several city blocks into oblivion. “It was the shortest graduation speech on record,” Williams is quoted saying in his biography.

Upon her death, his widow, Agnes Neill Williams, gave the largest single donation to the school in its history—a $23.5 million lump sum of cold hard CIA cash. 

The annual football game between Harvard and Holy Cross is still named after him: the EBW Classic.  

He was also, apparently, Larry Lucchino’s mentor—guiding the man responsible for bringing Polar Park to Worcester through his professional life, from law to sports management. To Williams, Lucchino was almost a son:  

If Williams had any ambitions for a son who would follow in his path, they were fulfilled by his protégé, Larry Lucchino.

On top of all the CIA stuff, Williams owned the Washington Redskins and later the Baltimore Orioles. It’s through Williams’ mentorship that Lucchino gets into the world of sports, first with the Redskins and then with the Orioles, where he built his first ballpark. 

Williams was also close with Lucchino’s mother: 

Larry Lucchino’s mother, a Pittsburgh housewife, came to a Williams party that was studded with celebrities from government and the sporting world. Sensing her unease, Williams put his arm around her and guided her around the room “like she was his date,” recalled Lucchino.

And at one point, they had cancer at the same time, leading to this delightful anecdote: 

One afternoon at the office, Lucchino was moping about, depressed, fatigued by chemotherapy. “Let’s go have some real chemo-therapy,” said Williams. He took Lucchino to the Metropolitan Club, where they sat drinking gin at three o’clock in the afternoon. Worrying and resting was not the solution, Williams insisted. Work was.

Lucchino and Williams would remain close up until Williams died, in 1998. Lucchino was a pallbearer at his funeral, and reported feeling “deeply alone” after Williams had passed.

It was Williams’ law career and all the CIA activity within that put him in the position to throw his wealth at sports management. It was Lucchino’s ties to Williams that set events of his career in motion that would culminate in his coming to Worcester in 2018. 

So basically we have the CIA to blame for Polar Park. What a world. 

Then, for extra fun, consider the fact former City Manager Ed Augustus is a Holy Cross man—at one time the school’s director of community relations. The Polar Park deal was very much the result of personal negotiations between these two men, one connected to Holy Cross and the other to the school’s most famous—and, I’d argue, infamous—alumni. 

Hm!

Thank you for reading! No odds and ends today. Make sure to read the Thursday edition if you haven’t yet—has all that kind of stuff.

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