The Godfather of Chicago Real Estate: Randy Pavlock From Hunter Properties

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The Godfather of Chicago Real Estate: Randy Pavlock From Hunter Properties

If you want a deep dish pizza, there’s a thousand places you can go in the city of Chicago.

if you’re craving a hot dog or an Italian beef sandwich – everybody’s got an opinion about who’s best.

But when it comes to renting an apartment on the North Side of the city, there’s one thing all the locals agree on. And it ain’t Zillow or It’s Hunter Properties.

Randy Pavlock is the big boss at Hunter Properties – and the godfather of real estate in Chicago. And when it comes to vintage architecture, cholera outbreaks,  Al Capone and all things Chicago – the man has plenty to say.

Right off the bat, I wanted to know what it was like to be known as the Godfather of Chicago real estate. So he told me.

“You know, I’m always surprised when people come up to me at things I go to like the Lincoln Park Builders Club  and say that I bought a building that they tried to buy and that I always beat them out of it. And that I’m their idol!” He says with a laughs.

“I’ve been around long enough I guess and when you’ve had some success, people get to know who you are.”

So what was it about real estate that hooked Randy early on?

“It was completely accidental. I started college with a scholarship got sick in my junior year. I was in the hospital for several months there for them to determine what was wrong. They found out I had a defective kidney. And they did the surgery I was in the hospital for three weeks. Medicine wasn’t quite as advanced. This was 1971. And after that was all over I missed most of my junior year. I lost my appetite for being in pre-med.”

“In order for me graduate in three years and with my class, I switched majors to English literature. I had a lot of classes in that subject already. And I graduated with my class with the degree in English and I was going to teach school.”

“My wife’s grandmother was managing a building and was going to retire. So she wanted to know if I wanted to take her place temporarily until I could secure a job teaching high school. So I took the building at 530 Barry in Chicago and wound up living in the building and managing the building.”

“It was 32 apartments. I took out the garbage and did all the repairs. A year later the building was purchased by a gentleman in the restaurant business who was going into the real estate business. Within another two years I was managing five different buildings; about 150 apartments and doing all the work in all those buildings.”

But Randy was just getting started. “In 1977 I wound up getting my real estate license. I started doing sales in addition to management. I wasn’t stuck in an office somewhere. I was always going from one building to another. So inadvertently I wound up learning all the trades. By having to do those things.”

“I learned that I liked to build things. So I self educated myself on the techniques of carpentry, electrical and plumbing. Which were rather invaluable in terms of managing a building the rest of my life. If you know the job, and you’re familiar with it, you have a better appreciation for what people are doing. How hard the work is. What’s appropriate to charge. What’s involved. And you know you have some respect for the people that work for you because you know that you’ve done it yourself. And you know how difficult it is.”

Randy’s never been afraid of doing the work. But as a Chicago native working in real estate, he quickly developed an appreciation for vintage buildings.

“You don’t become a manager or get in the real estate business if you don’t have some appreciation for the real estate. I have great admiration for the way old vintage buildings, primarily those built in the 1920s until the fire happened in 1929. They did a tremendous amount of building in Chicago in the 1920s. And its astounding considering that every two by four was cut with a handsaw. The bricks were being laid by hand. And there was complicated decorative patterns – a lot of terracotta. Work. Those buildings will last virtually forever if properly cared for.”

But some of the most interesting trademarks to Randy’s buildings have nothing to do with construction techniques. Trademarks like bullet holes.

Randy gets a big smile on his face. “922 West Eastwood”.

“We had purchased the building some years ago. It is a very nice terracotta facade building. The two top floor units are duplex apartments which is very unusual.”

“One of our tenants sent me a Tribune article about gangster who had been killed in front of this building in the 1920s. Which was something that I had never heard before. This particular gangster worked for a North Side syndicate run by a fellow named O’Banion who got into an argument with Al Capone. And people generally didn’t win arguments with Al Capone. He even challenged Capone to a duel on Madison Street once. Two Time Tony was his nickname.

“It was more or less a gunfight at the OK Corral. And a little too public an affair for Al Capone to get involved with.”

“Capone wound up killing O’Banion and some his guys most famously in the Valentine’s Day massacre. Which happened at the Biograph Theatre on Lincoln Avenue. Al Capone had taken offense to whole duel thing and instead hired some people to kill Two Time Tony.”

The story gets better. “They rented a unit in the building across the street. This was apparently a technique that was adapted by the guy they were about to kill. They had a sniper, a guy with a shotgun and a guy with a handgun from across the street.”

“They shot him from across the street. They waited in front of the building for when he and his wife came out. And as soon as he walked out of the building, the guy with the rifle started shooting and hit him several times. Then the guy with the shotgun shot at him as well. Did less damage. And as a follow up, the guy with the handgun ran across the street after Two Time Tony was wounded and shot him to make sure that he was mortally wounded.”

“They had a car waiting and took off. Of course they were never apprehended. Tony was taken by ambulance, and died in the ambulance, on the way to the hospital having been shot several times.”

So are there still bullet holes in the building?

“When we purchased the building, I noticed there were some holes in the facade which were unusual. Sure enough, after I heard this story, I went back over there and took some pictures and clearly there were bullet holes and a tear out of where they normally wouldn’t be. I find that to be pretty fascinating.”

Renters love being part of this kind of Chicago history.

“Many of the vintage buildings with a lot of studio apartments were built when the rail line was constructed along the lake. Most of those buildings provided things like linen service and all those other amenities which millennial’s at a time that weren’t downtown needed.

“I’ve had two buildings that had speakeasies in them,” Randy notes with no small amount of pride.

“One on Damen Avenue had a very elaborate kitchen sink I wound up keeping for myself so that I’d have something to remember the building by. I also had one at Chicago Avenue near Clark. It was also a speakeasy and that was part of a property for Harry Levinson who is a very famous jeweler in Chicago. I don’t even think he was aware of the fact that there had been this speakeasy upstairs.”

Randy takes a moment to reflect on his love of vintage buildings. “I know it’s trendy right now to like new construction. But I like stuff with a little bit of history. Compared to Europe where they have buildings that are 500 or 600 years old. Our history is very limited in relation to that.”
“I wouldn’t have done it so long, and worked so hard at it, if I really didn’t care,” Randy insists.

“When we go to look at a building to buy, I get a certain vibe from it. A feeling more than anything analytical. Obviously we’re concerned about the potential of the building. But there’s also generally a feel I get in a vintage building.”

Randy’s love for vintage bleeds over into the way he and his team painstakingly restore each building they buy. “I try to keep any vintage touches in that building and bring it back to the condition that it was what it was in its when it was originally built. Otherwise, It’s kind of like destroying history.”

“I try not to disturb anything. We’ll try to duplicate arches that are already there. Replace original lighting with fixtures appropriate to the period. Because nothing is worse than taking a brand new Home Depot fixture and sticking it on a vintage building. It diminishes the building.”

But for apartment hunters in the Chicago area, Hunter Properties has more than just the best units available. They’re also one of the most practical places to rent in Chicago.

Randy explains that, “I never wanted to be in the high end of the rental market. If there’s a recession, and I’ve probably gone through three or four of them in my time, the high end gets hurt the most and gets hurt the fastest.”

“I prefer to have nice entry level housing; studios one bedrooms. A lot of investors tend to frown upon studios. The feeling being that maybe the turnover rate is too high. But I’ve never found that to be entirely true.”

“Studios are usually the most affordable sector of the market. And if there is a recession and things go badly, you’re the last one to get hurt. Our turnover rate is about 15 percent. Apartment luxury buildings downtown, the turnover rate is between 55 and 65 percent a year. and that’s brutal.”

Brutal indeed.

The history lesson continues, “After the 1871 fire they built everything from brick. Our electrical codes in Chicago were the most stringent in the entire nation. Same thing with plumbing codes.”

“One of the reasons the fire spread so quickly was there were a lot of frame houses jumbled together. Quite flammable. So the mantra of the building department for the city of Chicago became working with lot of great architects that all had their own projects. They wanted to rebuild the city. So a lot of things happened then we got the opportunity to rebuild the city again from scratch.”

“Development followed places that had streetcars. Most of the major arteries in Chicago; Western Avenue, Irving Park – they had street cars. We tend to purchase buildings close to public transportation. Primarily the L tracks. Because  a lot of people have given up using cars in the city for various reasons. They want to be near public transportation.”

“In the late 1800s, the lakefront was the source of cholera outbreaks. It was a swamp. They were dumping. And the Chicago River flowed right into the lake until they reversed it. It got pretty nasty downtown. Not to mention the fact that we were the railroad capital of the Midwest. It was train tracks and a harbor for shipping. So it was pretty ugly for a long time and because of the pollutants in the Chicago River and sewage going into the lake”

But all that has changed. The story of Chicago is a success story. Like the story of Randy Pavlock and Hunter Properties.

“You have to have passion for what you do,” Randy begins to wrap things up. “I think you should have passion for treating other people as you wanted to be treated. I think you have to have care for your tenants. Care for your workers. Because after all, if I didn’t have my workers I wouldn’t have my tenants.”

Randy sums up his success thusly, “I’ve been successful trying to make money in an honest and fair way. Is it hard work? Yes. I think it kind of comes involved with always doing the next right thing. Just do the next right thing.”

“There’s something pure and good about work as human beings. It makes us feel good. That’s why it’s important to work it’s something that you like whether it’s lucrative or not lucrative. Follow your heart. Never ask somebody to do something that you’re not willing to do yourself. It can be hard to do. But I think it’s important. There are some terrible jobs. But you have to respect the people that do those terrible jobs. And what greater respect can you have than being being willing to do it yourself?”

“Isn’t that what makes a dignified?”

Looking for an apartment in the Chicago area? Visit: for the very best the city has to offer.