The road to opening wasn’t always smooth. Cianchette said in October 2023 that he was hoping to open at the start of the new year, but that fulfilling licensing requirements, solidifying a location, hiring staff and finding a partner in Caesars pushed the timeline back.

“It was making sure we thought everything through to be able to operate well,” he said. “It was (more) important for us to do it correctly than to do it quickly.”

Cianchette acknowledged that getting ready for the football season added an incentive.

“Earlier would have been better,” he said. “At the same time, this is when people are really interested.”

Soon after the mayor’s bet, customers began making their way in. One was Mac Simpson, a 39-year-old broker from Freeport who took $200 he made on a winning bet in Thursday’s Buffalo Bills-Miami Dolphins football game and turned it into a five-way parlay for Sunday (bets on five different players to all score touchdowns).

“It adds another dimension to watching sports,” Simpson said. “I honestly think in-person betting is more healthy, social, more entertaining, more fun to be there with a group of friends than sitting by yourself, placing bets on a phone. It doesn’t feel real when you’re pressing a button digitally. It feels real when you’re taking cash and putting it into a machine or giving it to a guy.”

Bernier, the letter carrier from Westbrook, said the state needed that option.

“When they passed it, I did download the app, I gambled for maybe a month or two. … But the in-person’s missing,” he said. “Sitting on your couch and betting is convenient, it’s fun, it’s easy. But to be able to come out … it’s the in-person thing that’s attractive.”

Some in the city have concerns regarding sports betting’s arrival. City Councilor Kate Sykes voted against Oddfellahs’ request for a liquor license, hoping to slow the bar’s arrival and give Portland more time to set up rules and limitations regarding gambling within the city.

Sykes, who joined the council in November, said statistics show a trend between male gamblers in their 20s and diminished credit scores. She also expressed concern about the parlor’s proximity to schools and said that the bar might not boost businesses as well as hoped.

Portland City Councilor Kate Sykes Photo courtesy of Kate Sykes

“(Casinos) are very inward-facing businesses, meaning that they tend to draw people in and never spit them back out again. It can have a detrimental effect on area businesses,” she said. “Whether that’s true with sports betting parlors, we don’t know. They’re new. But these are all considerations that I think impact the fabric of the market, and could negatively affect other bars in the area, other businesses in the area.”

Sykes said that she’s not against gambling, but is more concerned with Portland’s readiness for a betting establishment, saying that the city is “behind the eight ball.”

“I was shocked that we didn’t have an ordinance, and that we weren’t prepared for this,” she said. “Portland, of course, is going to be one of the first cities in Maine to have one of these, and that may be a great thing. But it also may require a little bit more thought and consideration around where they go and other things.”

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