Wolf and Jay: Two Landlords’ Approaches to a Troubled Neighborhood

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In January 2016, local Chicago newspapers ran the obituary of a Chicago landlord. His name was Jay Michael and he had died at the age of 34 after a long battle with non-Hodgkin’s lymphoma. He had made his name by investing in unused real estate in struggling neighborhoods. In October 2018, local Chicago newspapers ran the obituary of another Chicago landlord. His name was Louis Wolf and he had died at the age of 94 after years of failing health. He had also made his name by investing in unused real estate in struggling neighborhoods.

Michael’s obituary contains words such as “brainchild,” “creative,” and “forward-thinking.” Wolf’s is peppered with more sinister terms: “cautionary,” “ruthless,” and always in the same sentence with his name, “notorious slumlord.”

Two famous figures in the local rental industry, of the same faith, race and gender, working in the same neighborhood. One, born into wealth in the 1980’s is praised as a hero, although not without his critics. The other, born into poverty in the 1920’s, is condemned as the “worst landlord in Chicago history,” but was also a proud grandfather who is remembered by those close to him as a quiet and kind mentor. What can we learn about being a landlord from the divide between the two?

Make your money from both rent and sale.

Michael’s companies, Cedar Street Properties and FLATS Chicago, were known for purchasing known problem buildings in Uptown and Edgewater and renovating them to make micro-apartments. By subdividing the existing apartments into much smaller units and working to attract young professionals with far more amenities than the standard vintage apartment community normally offers, he was able to improve the resale value of the properties while returning them to working use as occupied residential structures rather than vacant eyesores.

Wolf’s m.o. was to buy decrepit buildings not for their own sake, but because he knew that the land they stood on would eventually grow in value to far exceed the purchase price. He would fill the units inside for as long as they were inhabitable, but would not do anything to keep them in livable condition. Eventually the buildings would decay to the point where demolition would be the only option remaining for a potential buyer. By doing this with many buildings up and down Broadway in Uptown and Edgewater, he kept his overhead low but also caused the ruin of numerous historic buildings, including the beloved Uptown Theatre.

Work with your city leaders.

The buildings that Michael purchased were headaches for local officials. Some were abandoned, others on the verge of collapse or used as drug and gang houses. By taking on the conversion projects Michael removing these troubled buildings from the to-do list of local officials. He got building permits for his work. He parleyed with protesters who accused him of gentrification, allocating some of his new apartments for low income renters. He made friends with the city council members and made a massive effort to remain on everyone’s good side.

Wolf broke laws. In the 1950s and 60s he was part of a small group of five men who owned about 2000 buildings in Lawndale, and they were leading the charge for blockbusting and redlining, selling properties to black residents in the formerly Jewish enclave that had been their home. The owners couldn’t get loans, so he would sell them on monthly payment contracts only to take them back when payments were missed and sell them again to another black family. When the buildings decayed he would burn them for the insurance. He was convicted of arson in 1969. In the late 1980’s he submitted plans to the city to construct three 3 story buildings at State and Division, but instead constructed a single four-story building without a permit. The city had to sue him to demolish it. In 1993 he was convicted for racketeering and mail fraud for failure to pay his property taxes.

Live publicly and share the rewards.

Michael used the press to his advantage. He was highly visible. He did reality TV. He did interviews with everyone. When he was diagnosed with the cancer that would eventually kill him, he did a whole blog series on living with a potentially fatal illness. He made sure everyone knew that he was investing the money he got from being a landlord into start-ups and local businesses. He understood the value of having a saved up cache of good PR to offset his work in a maligned profession. For every article that criticized Michael’s gentrification of Uptown, there were three talking about all the other cool stuff he was doing on the side.

Wolf had no similar extra-curricular activities. Almost every article I could find about him mentions how he refused to talk with the press. He was tight-lipped and secretive. Both men made a lot of maverick moves but Wolf had nothing good to offset the bad news every time he got in trouble with the law. The press really does want to find good things to include as a counterpoint in their coverage of people. (If they didn’t, we wouldn’t have a landlord¬† in the White House.) But the best they could do with Wolf was to suggest that his failure to pay taxes actually worked out for the better as it meant that well-meaning rehabbers could buy and save the Uptown Theatre for a very low price.

Never lose sight of class and race dynamics.

The unfortunate people who rented from Wolf were usually poor and black, elderly, or both. The uproar over his shoddy properties was not really originated by them, although they certainly complained. The trouble came from activists representing those tenants, highly educated defenders of the downtrodden. Powerful people tend to get upset when they catch you taking advantage of the protected classes. There was nobody with access to visible distribution channels who could speak up and say “hey, I live in a Wolf building and it isn’t all that bad.”

Michael rented his micro-apartments to young white professionals. When the anti-gentrification activists went on the attack, he had a whole army of happy, vocal, tech-savvy tenants to offer a counterpoint. When he conceded to the complaints and allocated a portion of his buildings for low-income renters, the rest of his units were already full with market rate tenants.

Your buildings are your legacy.

In all of the many articles covering the actions of Michael and Wolf, there is a glaring absence. There are no interviews with any of their tenants. Apartment buildings are investments, yes, but to their tenants they are home. There must have been thousands of people who lived in those buildings but not a single one was quoted by the media, and within a few years after moving out probably only a small percentage of them remembered that they lived in a FLATS or Wolf building.

But people know that Wolf was responsible for the ruin of the Uptown Theatre. And they know that Michael saved Lawrence House from demolition. Tenants will come and go. The buildings remain.

Greed must be tempered by altruism.

There is an imagined picture of the perfect “good” landlord in the minds of the general public. They are successful, but not to the point where they buy a Hummer and a mansion in Barrington. They put their tenants first and care for them in an almost parental way. It’s not too far off from the image of a “good” teacher, politician, boss. We like our authority figures to be completely benevolent Santa Clauses.

The reality is that landlords are investors first. If they weren’t interested in making money they wouldn’t buy rental property. When the practical desire for money collides with our ideals of “good” power brokers, we cannot allow both to exist in the same individuals. We immediately assume that the landlord is entirely a servant to their own greed, to the complete exclusion of their tenants’ well-being. And so the landlord becomes, in our mind, a “bad” landlord. There is no grey area.

Michael went on record saying that he saw nothing wrong with gentrification. But he spread his money around and he gave ground to allow LIHTC tenants into his renovated buildings. He saved historic buildings from destruction. He knew the popular sentiments and used them as emotional levers to offset his substantial success as a landlord and whitewashing of Uptown. It took an enormous public relations campaign that must have consumed the majority of his time, but he managed to display enough altruism to offset the “bad landlord” reputation. His death at an early age adds a heaping dose of tragic downfall to complete the picture of the hero landlord.

Post-mortem coverage of Wolf in his later years tried to rehabilitate him as well by talking about the community service work he’d done after getting out of prison. It was too little, too late. When we saw the kind and grateful comments on his obituary from those he had mentored in the real estate business we were a little surprised, even though have known many similar landlords with horrible public reputations who were wonderful people, but quietly so. He was loved by his family, who have refused to comment on his death to the many scavenger journalists looking for a scoop. He was a successful investor, he made a lot of money, he was respected by those close to him, we just never saw that side of him in the media, so all we know of him is “bad landlord.”


Without villains, there are no heroes. Things have to spiral down to the breaking point in order for a hero’s changes to be seen as good rather than scary. Without the big bad Wolf’s neglect of his houses of sticks and wood in the 1980s there would have been no grungy Uptown for Jay Michael to turn into houses of grey bricks in the 2000s.

Michael was not entirely a hero, and Wolf was not entirely a villain. But that is how they are remembered after their respective deaths. How about you? Would you rather be famous or notorious? What other differences can you pick out between the two landlords? Let us know in the comments.

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Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.