Donald Trump investigated several sites in Massachusetts for a potential Trump casino, but it never came to pass. Pictured here, the now-defunct Trump Taj Mahal in Atlantic City.

Donald Trump has found a new target for his wrath, blasting Massachusetts casino regulators as “crooked bums” who are “hugely stupid” and “clearly unable to understand my incredible, incredible genius” for pulling his license to do business in the state.

The Massachusetts Gaming Commission took the unprecedented action after Trump failed to make payroll for the third week in a row for the 3,000 workers at his Trump Boston Harbor, triggering riots outside the half-empty gambling hall.

In a campaign stop at his beleaguered waterfront casino, Trump blamed Hillary Clinton for “stirring up trouble” at his casino and threatened to “kick Massachusetts out of the union and right back to Mexico where it belongs” should the state vote for his Democratic rival.

OK, so that didn’t actually happen. But if Bay State’s long-winding road to casino legalization had taken a slightly different turn, we might be stuck cleaning up after another multibillion-dollar Trump business fiasco right in our own backyard.

Scott Van Voorhis

Scott Van Voorhis

Trump was for years a lurking presence on the state’s nascent casino scene as lawmakers debated endlessly whether or not to give a green light to Las Vegas-style gambling. But we can thank a famously irascible mayor and a convicted felon for ensuring that Trump never got a real shot at bankrupting yet another promising venture.

Trump made his first move – that we know of – back in 1996, when he tried to convince the late, great Thomas M. Menino to let him build a casino, condominium development and marina in Boston Harbor on Long Island.

Menino was even said to be ready to meet Trump on his home turf in New York to discuss the proposal, only to be a no-show. We can only speculate what spared Boston from falling into the Trumpster’s clutches, but a good guess is that Menino wasn’t having any of Trump’s billionaire tycoon act. Menino didn’t suffer fools or buffoons lightly; any display of boastful big talk on the part of a developer was a surefire way to anger the mayor and sentence a project to death by a thousand bureaucratic delays.

Just ask Don Chiofaro about that.

It’s too bad Menino isn’t still with us – I can only imagine how he would be grumbling away about Trump right now in his uniquely mangled but colorful syntax.

Blocked By DiMasi

Trump’s second move came a decade later, in 2007. Gov. Deval Patrick had rolled out grand plans for a trio of resort-style casinos, Trump was one of the first casino tycoons to take the bait, with his executives scouring sites across the state.

Trump’s minions had talks with the owner of the Plainridge racetrack – now Plainridge Park casino – in Plainville on the Rhode Island line, The Boston Globe reported at the time.

Apparently there were some nice chats with Gary Piontkowski, the longtime track chief who was ousted in 2013 for helping himself to more than $1 million from Plainridge’s money room, repeatedly taking out small sums over the years as if the business were his own personal piggy bank.

The big man’s flunkies also kicked around sites in Fall River, New Bedford and Warren, and chatted with the mayors of Holyoke and Chicopee.

Who knows whether Patrick would have fallen for Trump’s act, but he never got a chance.

Former House Speaker Sal DiMasi, now languishing in federal prison, apparently didn’t have a problem taking a kickback from a tech company, but he drew the line at gambling, torpedoing Patrick’s casino bill.

Trump’s interest in opening a casino in Massachusetts remained a matter of speculation for years after that. His well-known friendship with the Krafts and their short-lived push to build a casino next to Gillette Stadium certainly kept the rumor mill abuzz.

(Speaking of the Krafts, in another nightmare scenario, it might have been Trump, not Robert Kraft, who ultimately bought the Patriots. The Sullivans, the owners of what was then a hapless franchise, supposedly approached Trump in 1988 to see if he was interested in buying the team.)

The Krafts wound up teaming up with Las Vegas tycoon Steve Wynn on plans for a $1 billion casino, only to face an open rebellion from Foxborough officials and residents that killed the proposal before it even made it to a community-wide vote.

Wynn later resurfaced in Everett with a new casino plan, and after years of vetting, appeals and delays, broke ground this summer on his $2.1 billion Wynn Boston Harbor, the largest private development project in Massachusetts’ history.

We can only wonder what might have happened had Wynn taken a pass on Massachusetts after the Foxborough debacle and it was Trump who wound up competing for the Boston-area casino license.

It’s hard to imagine how far Trump would have made it in the strict vetting process run by the Massachusetts Gaming Commission, given his well-known history of declaring bankruptcy and racking up huge losses and debts. Then again, Trump might have made it just far enough to make trouble and file a lawsuit when his bid was rejected. If nothing else, Trump has proven to be master salesman, even if most of the time he is selling snake oil or worse.

Alas, we will never know what mad spectacle we were spared, but it surely would have been just that.

Imagine A World With Trump Boston

by Scott Van Voorhis time to read: 4 min
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