Milwaukee’s golden opportunity to finally get out of Chicago’s shadow has come

For decades now, the city of Milwaukee has been overshadowed by Chicago, the nation’s third largest city. When many people think of the Midwest — they tend to think of Chicago, first. The city with more skyscrapers than the whole state of California and Texas. The city with the seventh most millionaires in the world. The city with Michigan Avenue, the Gold Coast, the nice looking riverwalk, and the city where movies and television shows are being filmed on a regular basis, which is something you don’t see in most Midwest cities.

Chicago and its huge economy has dominated the Midwest on almost every level to the point that Milwaukee, the city just ninety minutes to the north, is often overlooked and underappreciated.

A couple of years ago, Milwaukee, gained national attention when Vogue magazine named the city “The Midwest coolest and most underrated city”.

To Miwaukeeans, the national press and its improved downtown, riverwalk and Fiserv Forum along with the dominance of the Bucks, and likely two-time MVP Giannis Antekounmpo had local residents thinking the time had come for Milwaukee to start getting the same respect as Chicago, Minneapolis, and other powerhouse Midwest cities.

Anyone who lives in Milwaukee or who follows the city could tell you how often the mayor Tom Barrett and local business leaders keep saying to the press that the city could compete with any city in the country.

Milwaukee even put in a bid to host the Democratic National Convention and won with probably a little help from the DNC Chairman Tom Perez, who met his wife in Wauwatosa, where they got married in Milwaukee, and his daughter is a student at the University of Wisconsin-Madison.

Before Milwaukee won the DNC convention bid, Milwaukeeans couldn’t turn the local news on without watching its local politicians and business leaders constantly saying the city is just as good as any other city, and how the city has changed so much over the past decades with the new developments.

Still, in some ways, Milwaukee was still just a small market city with big city dreams, which became apparent with the DNC convention bid as the city was competing against international cities like Houston and Miami for the chance to host the convention.

For an international big city having enough hotel rooms to host the event is an afterthought, but, for Milwaukee, it was a serious question since the DNC requires a host city to have 15,000 rooms within a 20-minute perimeter of the convention location.

The whole city of Milwaukee at the time only had 18,000 rooms including 5,000 rooms in its downtown area. For a city as large as Milwaukee those numbers are a bit low, and screams large city, not big city, and nowhere near an international city.

Chicago, the nearest big city, has over 100,000 hotel rooms and is still adding new hotels. At one point, Milwaukee mayor Barrett and other city leaders were telling the press about rooms in its surrounding suburbs. The Milwaukee DNC bid became more of a Milwaukee metropolitan area bid.

In Miami, some political leaders and donors were saying Milwaukee was not fancy enough to hold the DNC convention. A claim that those same political leaders and donors would not have made against Midwest big powerhouse cities such as Chicago, Minneapolis, Cleveland, and even Detroit.

Detroit with all of the bad publicity and population loss over the last decade or so is still a city with more than enough fancy hotels, restaurants and meeting areas to host the DNC convention.

The suggestion that Milwaukee, a city of about 600,000 is not fancy enough is a huge slap in the face, but than again it shows how the leaders in some big cities still view Milwaukee as a small market large city pretending to be a big city.

The city of Milwaukee is not considered an international city by many people in the country. Some people may argue that the city is a large city, but not a true big city like Houston and Miami. So the thought of Milwaukee getting to host the DNC convention over big international cities had whispers of favoritism, especially since many people were questioning if the city could pull off such a large scale event on its own.

The months after the announcement that Milwaukee had won the DNC convention bid followed by embarrassing news stories of delegates choosing to stay in hotels outside of the Milwaukee area, and even outside the state of Wisconsin.

The new plan was for 2,926 hotel rooms to be used by delegates in Wisconsin while 2,841 hotel rooms would be used by delegates to stay in Illinois.

In an interview after the announcement, Milwaukee mayor Barrett, went out of his way to make it clear that no delegates would be staying in Chicago.

Instead of Chicago, the delegates would stay in near-by Chicago suburbs like Rosemont, which is near Chicago’s O’Hare International Airport.

For mayor Barrett, he wanted to make sure people knew that delegates were not choosing the bigger Chicago with all its fancy hotels and restaurants over Milwaukee.

Staying out of Chicago must have been a big request by the Milwaukee officials. The last thing anyone in Milwaukee wanted was to be upstaged by Chicago on the national stage.

The DNC convention was built up by the city leaders as Milwaukee’s moment. The biggest advertising campaign and one of the biggest moments in the city’s history would happen at the convention. For a few days, millions of eyes around the world would be focused on Milwaukee, not its nearby neighbor ninety minutes to the south.

The DNC convention was to be all about showcasing the city of Milwaukee, its nice riverwalk, downtown area, the newly built state-of-the art Fiserv forum, and the city’s underappreciated restaurants, and shopping locations.

Instead, the coronavirus hit with a pandemic of the likes that few people (if any) expected. The DNC convention was more of a virtual event. Joe Biden, the former Vice-President, and democratic nominee was not in the city when he accepted the nomination.

Milwaukee’s golden opportunity had turned into a decent opportunity. Many in the city must have be disappointed, but watching all the looting that went on in Chicago’s wealthiest areas for the second time in less than two months; makes you wonder if it is possible for Milwaukee to steal some of Chicago’s attention and wealthy residents since some in the city’s wealthiest areas like the Gold Coast are wondering if they should leave the city.

Let’s be honest, some Chicago police officers can’t solve a murder if it happens in front of them. The gangs in the city are doing YouTube interviews and looters are looting Michigan Avenue and other parts of the city for hours as if the police do not exist. One female and male looter even broadcast their looting live on Facebook.

The gangs in Chicago take the CPD, mayor Lori Lightfoot, the state’s attorney Kim Foxx, and Governor J.B. Pritzker for a joke. They are not even trying to hide anything anymore as they post the time, date and location of their looting in advance on social media.

So the big question is: Will Milwaukee make a pitch for Chicago’s wealthy and other income residents who are tired of the crime and looting? In 2018, Wisconsin spent $1 million in advertising in Chicago on a failed attempt to lure the city’s millennials.

Now, maybe, Milwaukee, would like to try its hand at luring Chicagoans to the brewery city. The city is so close to Chicago to the point that the adjustment would not be so huge.

For those living in or near Chicago’s downtown area; the adjustment would be huge since Milwaukee does not have anything near Michigan Avenue or State street or the amount of Michelin Star restaurants, but the city could offer a nice urban downtown living option with less taxes of course.

The biggest problem would be the likelihood of a large number of Chicagoans choosing to move to Milwaukee over one of Chicago’s nice nearby suburbs.

The one thing the Chicago area has is a lot of nice suburbs from the many blue collar working filled areas to the ritzy Deerfield and Highland Park areas.

Still, Chicago’s struggle could be Milwaukee’s gain. The city of Chicago is quickly becoming a gang and crime paradise city. Rapes and robberies are happening in broad daylight in the crowded downtown areas like the police does not exist.

The local officials have not said a word about toughening the laws and minimum sentencing, because longer sentencing could likely stop or at least reduce most of the lawlessness along with holding the Chicago police accountable for their ineffective policing.

For all the news stories being reported in Chicago about the looting and crime in the city; the one thing Chicagoans did not hear or read about in the local news after the looting was the CPD response time to the looting, which is part of the problem.

The DNC convention was a big promotion for the city of Milwaukee even with the mostly virtual event. The city received a lot of national media coverage for months leading up to the virtual event. Many people who rarely thought of Milwaukee saw news stories about the city, which could lead to a boost in tourism revenue.

A boost in tourism revenue is a great thing for the city, but the city should be more focused on trying to replace Chicago as The Midwest City, but the leaders in Minneapolis would likely put their own campaign together to lure fleeing Chicagoans, and try to become the most dominant city in the region in the next decade or two since replacing the third largest city in the country or even being able to compete with a city with an economy bigger than most countries would likely take a decade or more of rapid decline and population loss.

If Chicago cannot stop the violence or its residents from fleeing the city; Minneapolis leaders could soon put together an advertising plan to lure Chicagoans, which was the case in 2013 when Minneapolis mayor R.T. Rybak visited the city with a new digital and print campaign to lure same-sex couples. It is possible for Minneapolis to benefit the most from a possible Chicago decline once the George Floyd protests settle down, but unlike Milwaukee, the city is still a six-hour drive from Chicago.

Milwaukee would be an ideal big city for Chicagoans looking to move. And I am aware of the city’s racial problems and crime areas as well, which exists in many cities.

No one is sure if Chicago would become another Detroit, which would be very unlikely to happen. What is sure is the possibility of the city losing 10–40k residents a year until the Governor, state politicians, and local residents realize the weak laws and sentencing are causing the problem.

The state of Illinois has become a criminal’s dream state with its lack of severe punishment for felons. Rehabilitation only works if people are willing to change. Letting harden felons back on the streets have caused the mess the city of Chicago is in. Now, the city has aldermen calling for the National Guards, which is a short-term answer. The long-term answer is to become a one strike state that locks felons up by the decade instead of the week.

Until the state of Illinois makes a change, the thousands of people leaving Chicago and the state must live somewhere. So, why not Milwaukee? The city leaders went for the DNC convention because they believed the city could compete with the best international cities in the country.

They wanted to send the message they keep repeating. The message that Milwaukee has arrived and is ready for the world stage and big name conventions. What better way to send the message that Milwaukee has arrived and is on the level of Miami and Houston than to go after Chicago residents, and their strong spending power.

Chicago, right now, is a vulnerable city. The next few months and years would be some of the biggest in the city’s history that will decide the city’s international standing. For Milwaukee, the moment is now for the city chance to finally get out of Chicago’s shadow. Such an opportunity probably won’t happen again.