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Meet the new casino boss. Holaday hopes to help Encore emerge from the pandemic

Dan Wolf comes in for his landing; It’s still not quite gala season; Pandemic “whack-a-mole” drags on for tourism chief; Connecting Massachusetts

Jenny Holaday, New Encore Boston boss.Chris Morris for The Boston Globe

Jenny Holaday started working in the casino industry as a college student, just as it was about to blossom beyond its roots in Las Vegas and Atlantic City. Career opportunities seemed to open at every turn.

Her circuitous career path eventually led her to Everett, where Holaday just became president of the Encore Boston Harbor casino, overseeing about 3,100 employees, after predecessor Brian Gullbrants relocated to Las Vegas at the behest of parent company Wynn Resorts.

Now, Holaday is determined to use her three decades of industry experience to continue the momentum the casino has seen since COVID restrictions were lifted in the spring. Encore exceeded $57 million in gambling revenue in each of the past four months — its four strongest months since opening in mid-2019 — and just enjoyed its most profitable quarter yet.


Holaday arrived as executive vice president of operations in October 2019, at a time when disappointing slot machine revenue hurt the casino’s numbers. The slot machines are seeing much stronger interest now.

“We spent a lot of time evaluating our slot business and figuring out the best practices from other regional markets and we’ve been implementing those changes,” Holaday said.

Revenue from table games, meanwhile, is almost back to pre-pandemic levels, even though poker won’t return until February.

Wynn also stripped out a buffet area that was losing $12 million a year, replacing it with a 14,000-square-foot sports bar called WynnBET with a wraparound TV screen. Wynn chief executive Matt Maddox boasted to investors last month that WynnBET is “probably the world’s best sports bar” — especially if, or when, the state Legislature finally legalizes sports betting.

The company also revamped its valet system, to prevent long lines of cars, and is doubling the size of its gift shop, dubbed The Drugstore, to keep up with demand.


Then there’s the activity across the street: Wynn is looking to develop four blocks along Broadway, starting with an 1,800-seat events space and a two-story restaurant; the casino operator is in talks with Ed Kane of Big Night Entertainment Group to manage the events space. The project also includes a parking garage and elevated walkway across Broadway to the casino.

The recent surge in COVID cases has caused some uncertainty. But the high vaccination rates in the Northeast, the casino’s main market, have Holaday hopeful.

She breaks down the early years of the casino into three chapters, with “rough start” and “pivot and learn” being the titles of the first two.

“Hopefully,” she said, “our third chapter is our fresh start.”

A well-timed landing

When Dan Wolf steps down as CEO of Cape Air at the end of the month, he won’t be flying off into the sunset.

The longtime chief executive is handing over the controls to Linda Markham, his lieutenant, on Jan. 1. Wolf, who turns 65 next year, will keep an office at Cape Air’s Barnstable headquarters and remain as the airline’s chairman. He’ll focus on strategic initiatives, such as figuring out how to electrify Cape Air’s 100-plane fleet.

“The only time I break into a cold sweat is when people congratulate me on my retirement,” Wolf said.

Here’s one strategic initiative he won’t be working on: starting seasonal seaplane service between Boston and New York. Wolf spent years trying to get that project off the ground before abandoning it in early 2020. (Rival Tailwind Air, meanwhile, pulled it off this year.)


Wolf, a Democrat and former state senator, ran for governor in 2014, and considered running again four years later. Will he take another swing? The timing of Wolf’s Cape Air announcement last Friday naturally sparked speculation that it was related to Governor Charlie Baker’s news earlier in the week that he would not seek another term.

No, Wolf said. The transition at Cape Air was long in the works, Wolf said, and he has ruled out running again in 2022.

“I know people are going to try to put two and two together and get five,” Wolf said. “But it was a total coincidence.”

An august gathering, but a small one

It was supposed to be a gala dinner honoring the two men who lead vaccine makers Pfizer and Moderna, in recognition of their companies’ efforts to help end the COVID-19 pandemic.

But in the end, the Edward M. Kennedy Institute for the United States Senate hosted just a few people in person on Thursday, including honorees Stéphane Bancel of Moderna and Albert Bourla of Pfizer, at the event, a reflection of the rising COVID-19 cases in the area.

Instead of a dinner, about 150 supporters tuned in virtually to watch NBC News correspondent Kristen Welker interview the chief executives, who received the Edward M. Kennedy Award for Inspired Leadership. Others on hand included: Ambassador Victoria Reggie Kennedy, Bank of America vice chairwoman Anne Finucane, and developer Bruce Percelay. (Finucane chaired the event for the EMK Institute, and Percelay chairs the institute’s board of directors.)


Percelay said he was disappointed at the last-minute change.

“A year ago, we would never have contemplated that we would still be having this discussion now,” Percelay said. “No one … is thrilled about it. But the reality is, better safe than sorry.”

Summer? Which summer?

But on the previous night, the Greater Boston Convention & Visitors Bureau was very much in person, drawing about 250 people for the bureau’s annual meeting at the Marriott hotel in Copley Square. It almost felt like old times again in the ballroom, except for all those face masks.

U.S. Travel Association chief executive Roger Dow, the featured speaker, talked about how dealing with the pandemic’s impact on his industry has been “the biggest game of whack-a-mole I’ve ever played in my life.”

Dow recalled a White House meeting, held in the early days of the pandemic in 2020, with then-president Donald Trump and several top aides.

“I said, ‘Mr. President, this thing could go all the way to summer,’ ” Dow said. “He said, ‘I think it could be over by Easter.’ I said, ‘summer.’ Well, I had the wrong summer.”

Build Back All the Way Across Massachusetts

Could the path finally be clear for higher-speed, more frequent rail service between Boston and Springfield? Representative Richie Neal sure thinks so. During a virtual Greater Boston Chamber of Commerce event last Thursday, he talked up his favorite transportation project now that President Joe Biden has signed a $1.2 trillion infrastructure package.


Neal, who chairs the House Ways and Means committee, said three Massachusetts congressmen sit on the transportation and infrastructure committee overseeing the deployment of these funds: Representatives Steve Lynch, Seth Moulton, and Jake Auchincloss. “Their priority,” Neal said, “is east-west rail.”

Also due for an overhaul: the Cape Cod Canal bridges, he told chamber chief Jim Rooney, and the perpetually backed-up exit where Interstate 84 joins the Mass. Pike.

Neal said he has needled Governor Charlie Baker about the pressing need for better east-west rail service.

And Neal asked Boston chamber members to help figure out how the western and central parts of the state can share in Boston’s economic success. Neal praised the quality of life there, with few Boston-style traffic jams to be found (I-84 backups on the Pike being a notable exception).

“Look at what happens trying to get out of Boston on a Friday afternoon,” Neal said. “I said to Governor Baker, ‘You could be there for days, never mind hours.’ ”

Unfortunately, that might be a problem that no federal funding windfall can solve, no matter how large.

Jon Chesto can be reached at jon.chesto@globe.com. Follow him @jonchesto.