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Long before Alex Cora, Boston has been a city of cheats

Clockwise from top-left: Rosie Ruiz received her crown after being the first woman to cross the finish line during the Boston Marathon in 1980; Colts linebacker D’Qwell Jackson intercepted a pass intended for New England’s Rob Gronkowski in 2015; Mayor James Michael Curley returned to Boston from prison in 1947. “The Gerry-Mander” cartoon first appeared in the Boston Gazette in 1812.David L. Ryan/Globe Staff/File/1908; Julio Cortez/Associated Press/File/2015; Charles Dixon/Globe Staff/File/1947; Wikipedia.

If you ain’t cheatin’, you ain’t trying, the old adage goes.

And here in Boston, no one’s ever accused us of being slackers.

News this week that (now former) Red Sox manager Alex Cora masterminded a brazen dugout sign-stealing scheme served as just the latest example of our fair city’s tenuous relationship with the rules.

Long before those nefariously deployed Apple Watches in the dugout, and even before deflated footballs and Spygate, Boston had a strong claim to the title of most crooked city in the land.

It is the birthplace of the Ponzi scheme, after all. Gerrymandering, the infamous political scam of rigging districts to secure power, was named after a Massachusetts governor back in 1812.


Boston not only elected a man nicknamed “The Rascal King” as its mayor in 1945, but did so while he was under federal indictment for mail fraud. Let’s not forget three successive House speakers who, from 1996 to 2009, fell to felony convictions.

And then there’s this to consider: Ashley Madison, a website that helps married people facilitate affairs, last year put Boston on its list of top cities for infidelity.

“I don’t know what it is in the water here that has led us to sort of go down this road,” says Tony Massarotti, a host on 98.5 The Sports Hub. “But it does feel like it’s a little out of control.”

Cheating knows no geography, of course; open a newspaper in any American city and you’ll read about a variety of crooks and swindlers, scoundrels and cheats.

But there is something endemic about it in Boston — where we don’t just tolerate the occasional bending of the rules, but take a perverse kind of pride in it.

“Manipulating rules and procedures was always part of Boston,” says Peter Drummey, librarian at the Massachusetts Historical Society. “Cheating is seen as being sort of clever, a sign of sharp-witted . . . manipulation, rather than being evil, or even scandalous.”


Even out-of-towners, upon entering the city limits, seem afflicted with a sudden aversion to the rules.

In what might be the most brazen example in modern-day sports history, New Yorker Rosie Ruiz arrived in Boston in April 1980 and proceeded to win the women’s division of the 84th Boston Marathon — except, of course, she didn’t.

In the days following the race, officials determined that Ruiz had run only a portion of the course, likely jumping into the race near the finish line.

Indeed, as the recent Red Sox scandal suggests, the city’s clubhouses, arenas, and playing fields have long provided a canvas for inventive transgressions.

Red Auerbach, the legendary Celtics coach, is rumored to have instructed staffers at the old Boston Garden to jack up the heat in the visitors’ locker room in an attempt to drain opponents of their energy. It can be almost impossible to keep the Patriots’ various scandals straight.

And back in the late ’70s, the Boston College men’s basketball team was involved in a point-shaving scheme that would make a few minutes of illegal sideline footage seem quaint.

Working with the same mobsters who would later be depicted in Martin Scorsese’s “Goodfellas,” members of the Eagles talented 1978-79 squad allegedly accepted money to manipulate the scores of games — and, subsequently, the Vegas gambling payouts.

But what in other places might be viewed as a fatal character flaw can, in Boston, serve as a kind of badge of honor. Bostonians idolize Patriots coach Bill Belichick, a man with the charisma of a sedated bullfrog, not so much in spite of his team’s tenuous relationship with the rule book but in part because of it. A genius who’ll do anything to win.


In Southie, there are still those who view Whitey Bulger — a murderous government informant who shattered countless lives — as a local folk hero, an old-school neighborhood guy who figured out a way to juke the rules a bit in order to tilt things in his favor.

And judging by the Downtown Crossing restaurant still bearing the name of Rascal King James Michael Curley, the laundry list of transgressions he carried out while mayor and Massachusetts governor have done little to dampen his legacy.

“There’s something about Massachusetts political culture that likes a little rascal every now and then,” says Peter Ubertaccio, dean of the School of Arts and Sciences at Stonehill College. “There’s a cultural trait that allows us to view people like Curley as merely a rogue who was working on behalf of the working class and others who had typically been outsiders in our political process.”

The root of this may be a deeply entrenched us-versus-them hard-headedness, a kind of civic defiance that can be summed up in the words of Bob O’Brien, a 48-year-old Sudbury resident who spent Wednesday afternoon lunching at a Fenway restaurant.


“They hate us,” he said, “‘cause they ain’t us.”

If nothing else, our city’s extensive experience with cheating seems to have produced a talent for snuffing it out ourselves.

Take last year’s explosive college admissions scandal, in which an extensive collection of celebrities and wealthy parents were accused of illegally paying vast sums for schemes to get their kids into college.

Though most of the alleged offenders were based in California, it was federal prosecutors in Boston who would ultimately break the case open — a fact that should well serve as a warning to the rest of the world:

Never try to cheat a cheater.

Globe correspondent Meghan Sorensen contributed to this report. Dugan Arnett can be reached at dugan.arnett@globe.com. Follow him on Twitter @duganarnett.