Monday night, the Milwaukee Journal Sentinel published a damning article on the leadership—or lack of leadership—of the Milwaukee host committee for the 2020 Democratic National Convention. It seems that two top officials, President Liz Gilbert and Chief of Staff Adam Alonso, are under investigation for creating an “unacceptable and upsetting” work environment. In addition to overseeing a “toxic culture rife with power struggles, backbiting and mismanagement,” Gilbert and Alonso are accused of “giving contracts to their friends in New Jersey, calling meetings and then failing to attend them and being more focused on accumulating power than promoting Milwaukee.” Fun!

Roughly five months remain until the 2020 DNC takes over Milwaukee July 13-16. So what else could go wrong? Plenty. While we’re still optimistic and excited for Milwaukee’s time to shine this summer, these seven screw-ups could put a further damper on the big event.


Wouldn’t it be great if, during the 2020 DNC, Milwaukee-area bars and restaurants could stay open until 4 a.m. in order to cash in on the expected 50,000 visitors? Yes it would! So who better to have a say in the matter—and likely kill the matter—than a Republican from Rhinelander? Yes, a committee chaired by Rep. Rob Swearingen (R-Rhinelander) would have to approve the late-night bar time proposal; Swearingen, however, wants to combine the proposal with a completely unrelated proposal that would require “wedding barns” to have liquor licenses. Why? Because Swearingen is a former president of the Tavern League, and the Tavern League hates those darn “wedding barns.” Also, Swearingen and his wife own the Al-Gen supper club in Rhinelander, so be sure to tell them how to run their business the next time you visit.


Oh wait, this one isn’t even up for debate. The Milwaukee streetcar will not be expanded in time for the DNC. Happily, 50,000 people will still be able to enjoy the route’s handy Milwaukee-Public-Market-to-the-Panera-Bread-by-the-East-Pointe-Pick-‘n-Save route.


File this one under An Extremely Good Problem To Have. As the Journal Sentinel notes, the 2020 NBA Finals begin June 4, and could run through June 21. If the Milwaukee Bucks keep winning and end up in the Finals, they’ll play some of their games in Milwaukee’s Fiserv Forum—which will host the 2020 DNC roughly three weeks later. That could create “logistical challenges, especially when it comes to preparing the arena for the once-in-a-lifetime DNC, an event unlike any others that have been held at the venue.” Again, this is a very, very good problem to have. So GO BUCKS.


The security footprint for the 2020 DNC will be a big one, covering about 75 city blocks and bordered by “West Cherry Street on the north, Water Street on the east, West Clybourn Street on the south and North 10th Street on the west.” And while some media outlets claim that businesses inside the footprint will remain open for business as usual, at least one Milwaukee alderman isn’t so sure. At as recent meeting, Ald. Bob Bauman worried that the DNC will cause a “great deal of disruption.” Even worse, he might not be able to see his dentist the week of the convention.

“My question was when will we know the details?” Bauman said. “Normally not until that (convention) week or the days before. As a general matter, the public can expect a great deal of disruption.”

He cited as one example of how businesses are affected that his dentist inside the security footprint will close for the entire week of the convention.

Also, it’s a big-time convention. Probably the biggest Milwaukee will ever see. Sorry you won’t be able to park directly downtown for a whole week.


There’ll be plenty of protesting during the DNC, though it’s likely none of it will happen inside the security zone. Enter activist group Coalition To March On The DNC, a “broad national coalition of left and progressive forces” that is currently making a stink over being denied a permit to, well, march on the DNC. “They don’t want protest, they don’t want demonstrations. They want to paint a picture for the world that Milwaukee is a city without problems,” says spokesperson Ryan Hamann. So good luck with that (we’re fans), and expect the official demonstration zone to be located somewhere in Waukesha.


It seems a day doesn’t go by without Milwaukee topping another list of Best Places To Visit In 2020 Because Duh, The 2020 Democratic National Convention. But what happens if, during the convention, the fawning travel press turns on Milwaukee like they did when the city hosted the ill-fated 2002 Major League Baseball All-Star Game? (The game ended in a tie.) Here was Sports Illustrated writer Tom Verducci back in 2002:

“Keep the game out of Milwaukee. It’s a fine, friendly city, but let’s be honest. The only reason the game was held in Milwaukee was because Selig helped use it as a chip toward getting taxpayers to help build him a new park. […] Milwaukee might be equipped to host porcelain bathroom fixture conventions, but an All-Star Game? Forget it. The city was so eager to show the world its sophistication that it housed the international media contingent 15 miles away from downtown in roadside suburban hotels.”

Yeah, the Milwaukee of 2020 is a lot different than the Milwaukee of 2002, but still. Here’s hoping our 8,000,000 new hotel rooms are up to snuff for the likes of CNN, the BBC, and Teen Vogue.


The 2020 DNC is being billed as the Most Important Event in Milwaukee History—it’s gonna have a $200 million economic impact!—but, who knows, maybe the whole thing ends up being kind of underwhelming? “City officials view these events as the opportunity for economic impact and large-scale investment,” says David Wachsmuth, a professor at Montreal’s McGill University. “The evidence is clear that this doesn’t always pan out. These events can’t always be transformative. But that hope is more or less omnipresent.”

A recent piece in Curbed expands on Wachsmuth’s thoughts:

Attempts to boost U.S. cities’ economies by hosting political conventions have had mixed results. A study by Cleveland State University’s College of Urban Affairs found that the 2016 Republican National Convention didn’t live up to expectations for its host city, generating a financial impact of $142 million, about 30 percent below estimates. The number of visitors to Cleveland for the convention also fell short of projections by 11 percent.

But whatever. Despite current snafus, the potential for further snafus, and the general lack of excitement surrounding whoever the Democrats decide to run against President Trump, we remain excited for the DNC. Bring on the national attention! Bring on the scrutiny! And hell, even bring on Fox News, who will be setting up shop in the new Deer Camp bar and in the parking lot of Usinger’s. Sounds about right.

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Co-Founder and Editor

Matt Wild weighs between 140 and 145 pounds. He lives on Milwaukee's east side.