Dan Jacobs, a contestant on the newest season of “Top Chef,” is having a national star turn with his soups, cheese treats and elevated snacks — and his open struggle with a rare degenerative disease.
But that publicity has not translated to a surge of prospective customers booking soirees at his Milwaukee restaurants, DanDan and EsterEv, ahead of the Republican National Convention, which is just three months away.
“We haven’t gotten one single inquiry, like nothing,” said the restaurateur. “That’s where I think everybody’s like, ‘What’s going on?’”
With the Republican convention slated to kick off in Milwaukee on July 15, some of the city’s biggest and most sought-after restaurants, concert halls and other venues are alarmed at how slowly the expected events around the gathering are taking shape.
Birch, whose chef, Kyle Knall, has twice been nominated for a James Beard Award for the best chef in the Midwest, has no signed contracts, and indeed has received only one inquiry, restaurant management said. The gracious, old-world Pabst and Riverside theaters also remain unbooked, according to entertainment industry officials. Leslie West, who co-owns and runs the Rave, Eagles Club and Eagles Ballroom, said she had given up and would “just book our own shows during the R.N.C. time period, no need to stress about it.”
“We’re seeing what everyone else is seeing,”said Adam Siegel, whose restaurant, Lupi & Iris, is finalizing contracts on two 100-plate brunches but has not seen the complete restaurant buyouts he was expecting. “There’s no sense of security that it will move forward in the way that most conventions move forward.”
His co-owner, Michael DeMichele, later pronounced himself “thrilled about brunches that are being booked.”
Last August, when the Republican Party chose Milwaukee to host its convention, the city’s Democratic mayor, Cavalier Johnson, promoted it as “full of unexpected gems” and urged conventioneers and partygoers alike to “take all your money to Milwaukee, spend it that week and leave it.”
Now, theories abound in Milwaukee about why bookings are off to such a slow start. Among them: turnover of convention staff after the presumptive nominee, former President Donald J. Trump, cleaned house at the Republican National Committee; a small city lacking event infrastructure; and a reluctance by would-be conventioneers to participate in an event showcasing Mr. Trump and his most ardent followers.
Republicans involved in the planning of the convention say that the concerns are overstated, that fund-raising is ahead of schedule and that bookings are actively being worked out between groups and venues. The R.N.C.’s Committee on Arrangements cited 50 events that “have already been signed or are moving to contract in short order.”
“The fact is the incredible support from the Milwaukee business community and beyond has put this convention in an unprecedented position for success,” said Reince Priebus, a former R.N.C. chairman and Mr. Trump’s first White House chief of staff, who now chairs the Milwaukee host committee. “We’re ahead of previous host committees in our fund-raising efforts, and ahead of schedule on our financial and other goals.”
And some bookings are coming through. The Bradley Symphony Center has “confirmed bookings,” said Rick Snow, the center’s vice president of facilities and building operations, with “additional events in the works.”
“A lot of work will start coming together now,” he said. “People who have done large-scale events before know things really come together in the final weeks of planning; it’s the nature of the beast.”
But about 100 miles south in Chicago, the city that will play host to the Democrats about a month after Milwaukee, the beast’s nature has been the opposite, organizers and event planners said. Navy Pier is booked up. Its Offshore Rooftop restaurant and another popular penthouse bar overlooking the lake, Cindy’s Rooftop, have multiple contracts, as does Chicago Cut, a popular steakhouse on the Chicago River. The Salt Shed, which has a capacity of 3,600, is signed for concerts.
Kimball Stroud, a Democratic event planner, said so many theaters were taken in Chicago this spring that she “dug deep” and discovered the newly renovated and opened Ramova Theater in the working-class neighborhood of Bridgeport, and then bought it out for two nights: one for former Representative Gabrielle Giffords’s gun-control organization, another for a yet-to-be-disclosed client. She is trying to get a third night as well.
Republicans involved in the convention planning say business in Milwaukee should begin heating up soon, though. Democrats putting together their convention in Chicago, a much larger city, had the advantage of being able to book the state delegations quickly into eight hotels downtown. In Milwaukee, though, the G.O.P. just sent out hotel assignments to delegates in late March — in 110 hotels scattered around southern Wisconsin.
Delegates, corporations, lobbying firms and trade associations may have been waiting to know where those hotels would be located before they would be ready to sign contracts for restaurant gatherings, concerts and warehouse parties.
Evan Hughes, a co-founder and the chief executive of Central Standard Distillery and Central Standard Crafthouse & Kitchen, said Friday he had three evening buyouts booked and three proposals in negotiation. CNN and Politico are expected to open a joint dining and media center, most likely at the same decorous downtown Turner Hall venue that the media organizations had booked for the aborted 2020 convention.
Mr. Hughes said he had heard from several planners that groups had prioritized securing venues for the Democratic National Convention in Chicago, and that they were now “turning their focus to Milwaukee.”
But if Mr. Trump is involved, white knuckles tend to follow. Venue managers say upheaval at the Republican National Committee, after Mr. Trump became the presumptive nominee and began installing an even more loyal team, has meant business partners have dropped out and been replaced by new faces. Prospective customers have asked for clauses in contracts to hold them harmless in case Mr. Trump simply calls off the convention.
“This is a great opportunity for our city to shine,” said Mr. Siegel, of Lupi & Iris, “and that’s all we want, for our city to shine.”
In 2020, Democrats opted to hold their convention virtually because of the coronavirus pandemic, canceling on the city of Milwaukee as hotels and businesses emptied across the country. Republicans staged part of theirs at the White House, a radical break from tradition that mixed politics with the trappings of governance and prompted Democrats to charge the Trump administration with a litany of Hatch Act violations. (The law generally bars government employees from participating in partisan activities.)
Eight years later, Mr. Trump is a known quantity, and his presence is far more of a complicating factor. One Milwaukee bar, the Mothership, announced last month that it was closing down for the convention, because, the owner, Ricky Ramirez, said, “I’m not trying to get involved with or actively take money or rent the space out to that tomfoolery.”
Some organizations will have a toehold in Milwaukee as they go all in on Chicago. The Latino Leaders Network will hold a reception at a Milwaukee law office for about 150 people, said the group’s chairman, Mickey Ibarra. It is holding a blowout on Navy Pier for 750 guests, with a contract that allows it to expand to 1,000.
“There will be a very big difference,” he said.
But even in Chicago, there is some concern that, beyond labor unions, state delegations and liberal interest groups, major corporations could be shying away from the Democratic convention, because those businesses are also shying away from the Republicans, said Sam Toia, the president of the Illinois Restaurant Association. As in Milwaukee, conversations are happening with such companies, but contracts have yet to be signed.
Skittishness from deep-pocketed corporations may be keeping some of the largest, priciest venues out of the conversation. The Milwaukee Art Museum, with its panoramic views of Lake Michigan designed by the renowned Spanish architect Santiago Calatrava, will not be hosting private parties, for instance, convention and Milwaukee officials said, citing cost and a desire not to entangle the museum with politics.
In some cases, there has been a clear mismatch in expectations. The Riverside Theater had planned to charge one group $116,804 for a film screening, an open bar and appetizers for 50 people, according to an invoice obtained by The New York Times. The venue remains unbooked, entertainment industry officials say.
Numerous businesses say that, three months out, such disputes should have been long smoothed over. By February 2020, just before the pandemic threw plans into chaos, much of Milwaukee was already booked for the summer Democratic convention.
Ms. Stroud, the Democratic event planner, said that, by February, she had been looking into building a temporary floor over the fixed seats at the Pabst and Riverside theaters to let partyers dance and mingle. And Mr. Jacobs, the Milwaukee restaurateur, said he had been selling single tables for a day at $1,000 a seat, as Democratic conventioneers nailed down places to hold court.
There is a potential cost to the slow start. Like other Great Lake cities, Milwaukee comes alive in the summer. The convention will put much of the city off limits in the middle of July, and send locals scurrying out of town.
“If we don’t see the business, I don’t think our locals are going to be here to support us,” Mr. Jacobs said. “With the D.N.C., we never felt this level of trepidation.”
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