Game Changers

Wynning! One casino magnate has had a very good few years.

With his $2 billion casino gamble, Steve Wynn took on two Boston mayors and won.

Medford, MA - 3/15/2016 - Steve Wynn laughed after learning that his people had not invited Somerville Mayor Joseph Curtatone to a meeting of local mayors to view the plans for the proposed Everett casino after a reporter asked him if Curtatone was in attendance during a press conference in Medford, MA March 15, 2016. Jessica Rinaldi/Globe Staff Topic: 16wynn Reporter:
Jessica Rinaldi/Globe staff/file
Steve Wynn unveils Wynn Boston Harbor.

Sometimes, it takes an out-of-towner to show it’s possible to go up against Boston’s most powerful politician — a brash, trash-talking out-of-towner, particularly one with deep pockets. On the local gambling front, that’s Steve Wynn.

The Las Vegas casino mogul essentially took on two Boston mayors with his vision for a Greater Boston gambling palace. Wynn, of course, is building that $2 billion fortress on the banks of the Mystic River, the largest private single-employer development in the state’s history. While his casino and hotel will be just over the Boston city line, in Everett, Wynn still needed to tangle with mayors Thomas M. Menino and Martin J. Walsh to get there.

Wynn originally wanted to build on the South Boston Waterfront, but Menino sent him packing. He then tested the waters in Foxborough, but residents there chased him away. Finally, Wynn settled on Everett, a down-on-its-luck city eager for the 4,000 jobs his casino would bring.


Wynn emerged as the only developer brave enough to challenge a casino plan by Suffolk Downs for the sole Boston-area license. The Suffolk project was widely viewed as a sure thing, in part because co-owner Joe O’Donnell was close to Menino. But Suffolk’s political connections didn’t seem to help much with the Massachusetts Gaming Commission or the voters in East Boston.

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Walsh was in charge at City Hall by 2014 when the Gaming Commission voted 3-1 to back Wynn’s proposal. After the frustrated new mayor and Wynn couldn’t reach an agreement on the mitigation package for the city, Walsh took the issue to Suffolk Superior Court, hoping to give residents in neighboring Charlestown a chance to vote on the casino to be built at their doorstep. But that lawsuit was killed by a judge in December, and Walsh and Wynn struck an awkward truce.

Plenty of questions remain. Who knew about the casino property’s ties to a convicted felon, and when did they know it? Can an angry Somerville mayor, Joe Curtatone, be placated? And will Wynn come knocking at the State House door, looking for a tax cut, if a tribal casino opens in Taunton?

But for now, at least, Wynn has reason to celebrate. A major out-of-state company took on Boston’s political establishment and won. Wynn Boston Harbor is designed to be a high-end, 24/7 entertainment complex capable of drawing tourists from around the globe. However, the impact this will have on Boston’s economy is not exactly clear.

But the casino saga proves at least one thing: It’s risky going against Boston’s mayor, but for the right gambler, the bet can pay off in a big way.

Jon Chesto is a Globe staff writer. Send comments to