Jazz Institute of Chicago

The DuSable Hotel and the Drexel Square Area

by Charles Walton

My first visit to the DuSable area was at night in 1946. I was in awe. The area was all lit up and alive with so much street activity. I had never seen anything like that before. Picture the Las Vegas Casino Strip or Burborn Street in New Orleans and then you can maybe visualize my amazement.

Looking south on Cottage Grove and on the west side of the street was a Walgreen Drug Store, east of there was a Power's Cafeteria, Nate's Men's Wear, a 5 & 10 cents store, a card shop and office supply store, a lingerie store, a hamburger snack shop and around the cornerwas the DuSable Hotel. All in all, this was a thriving community.

In 1950, while I was working for the Chicago Health Department I bought a car. I would drive many nights around to 39th and Cottage Grove, park in front of the Powers Cafeteria and watch, with other regulars, all the activities of the people on the street.I also visited that area during the day. A friend worked in Nate's Mens Wear which was on 39th and Cottage Grove and I would go by to see him from time to time.

Oakwood and Cottage Grove, looking north on Cottage Grove 1892. What would become the Morocco Hotel is on the right. (Courtesy of the Chicago Historical Society.)

I would stand outside of the Macombo Lounge, near the curb, and I would see the musicians, thru the lounge windows, performing in the club.Everybody came through there. Sometimes Leonard and Phil Chess would come out to the curb, stand next to me and confer with each other on something going on in the club. I didn't try to listen to them and they paid no attention to me.

There was so much going on. The area was very accessible because it was easy to get to Lake Shore Drive, going south, and exit at Oakwood Blvd.


"In its heyday, the DuSable Hotel was a major landmark in Chicago for Blacks. If a Black person visiting in Washington, D.C., inquired as to where to locate someone, the answer would be, "Go to 7th and Tee." In Detroit, the "Gotham Hotel," New York, the "Theresa Hotel," and in Chicago, you would be directed to the DuSable Hotel, 764 East Oakwood Boulevard."

CHARLES DAVIS, of Davis & Associates, a former Chicago Defender newsman, and DuSable Hotel employee:

"The DuSable was one of the "new hotels" where many travelers stayed. According to the jargon of people who worked in the business, it would be what you would call a "fast house." Entertainers, show business people, entrepreneurs, of a sort, some gamblers and so forth, stayed there and people who were traveling in the normal course of their business. It also had a few permanent residents and of course, these ranged all the way from "whores," who were plying their trade to business people, some professionals, and a delightful family of spinsters by the name of Jackson.

There were suites in the hotel and most of the permanent residents had them. There were a couple of policemen who kept ladies there.

Julius Soloway and Ben Cohen formed a corporation and bought the old Allen Hotel which later became the DuSable Hotel. At the time of the purchase, they were already associated in other businesses. Soloway knew real estate and Cohen was investing in the property with a partner who saw to the management of the hotel. The title was put in trust. That's the typical way to handle real estate in Illinois. With the title in trust, it's difficult to find the real owners.

Cohen and Soloway bought the building from a trust and they sold it to Katherine Noonan and she in turn put it in a trust and later sold it to Urban Renewal.

When Cohen and Soloway bought the Allen, it was boarded up and had been empty for some time. These fellows did a redecorating job and opened it up as the DuSable Hotel.

Oakwood Boulevard was primarily white. Most of the Blacks lived north of 39th Street. There were just a few Black families living on Oakwood Boulevard in the late 1930s. But that entire area was slowly yielding to the pressure of Black expansion, and ultimately Blacks occupied just about all the property along Oakwood Boulevard, and all the property east of Cottage Grove and south of Oakwood.

The DuSable Hotel was seemingly an instigator of this change. But, in addition to being an agent of change, it was also a product of change. It represented a kind of landmark and a high-water mark in that expansion. When Blacks occupied it, it was at the outer reaches of our residential area, although we had been shopping in the little shopping area at 39th and Cottage Grove for many years.

39th and Cottage Grove was a very busy area. It was predominantly white and stayed white for a long time after Blacks moved into the area. Drexel, Cottage Grove and Oakwood all converged at 39th Place. Oakwood began at South Park (now King Drive) and ran east to cross Drexel and Cottage Grove and ended at the lakefront a half block south of 39th Street. This area was a very convenient place for restaurants and other stores that provided retail services, including a drug store and a chain grocery store. One block of buildings had offices over them many rented to professionals such as doctors, lawyers, etc.

It was a really unique community. Four Police districts converged there: the Hyde Park Police District ended at Oakwood Boulevard, the Wabash Avenue Police District ended at Cottage Grove on the south side of 39th Street, the Stanton Avenue Police District ended on the north side of 39th Street and the Park District police had jurisdiction over all of the Boulevards.

Right across the street from the DuSable Hotel was the Drexel Bank. At that time they were not interested in minority business. Blacks could deposit there but it was a rare Black person who had a checking account. That practice lasted right up to the 1950s. The bank gave no loans or mortgages or anything like that to Blacks. The president of the bank during those years was Clarence Hoffenberger.

The average Black person could have a savings account, but not a checking account. That was the pattern citywide.

On the Southeast corner of Oakwood at Drexel was the Drexel Arms Hotel. Later, they changed their name to the Morocco. In the same block as the DuSable Hotel was the Oakwood Manor. That hotel was owned by a Jewish family named Sugar. The reason I remember is because I once worked for the Sugars. In fact, I also worked at the Drexel Arms, as a bellboy.

The DuSable was a beacon high point for us Blacks. It was not like a commercial hotel as in the Loop. It was an economic center and it worked just by being there. It didn't quite have that character, but it did attract Black travelers from all over the country. By having the bar downstairs which was such a success, other people decided to open taverns in the area. The businesses in the vicinity were able to cash in on the money being spent in the community because of all the people coming and going around there.

Different types of lounges were opened. Leonard Chess had the Macombo Lounge, there was the Palm Gardens on Oakwood Boulevard, across the street was the Morocco Hotel with its Lounge.

Policy playing [numbers] was a big business around there, too. Some people say that if it hadn't been for Policy, we would have been in even greater economic trouble. During that time, Policy gave employment to a lot of people. It was taking pennies and nickels, but it was giving people a chance to win, and it made some available jobs and it created a class of businessmen that otherwise would have had no way of accumulating capital to go into business.

There is no question that integration changed the character of minority hotels. When Blacks found that they could go into the downtown area, they went there in droves. And to stay open, hotels in the community had to become hotbed hotels to economically sustain themselves."

Because of the changing face of the population along Oakwood Boulevard, Cohen and his partners decided to "turn the hotel over" to Blacks. [This meant catering to a Black clientele—not transferring ownership.] The Allen was in a state of disrepair and Cohen closed it for renovation and refurbishing.The building opened again as the DuSable Hotel in November, 1941, amid fanfare and publicity as the showplace of the South Side.

Cohen had spent $120,000 to remodel and refurbish the building. He felt that he would recoup his money in five or six years. He actually got his investment back in two.

When the DuSable opened, Bill Johns was brought in to manage the hotel. He had worked as a bellboy and manager in several other small hotels owned by the syndicate. However, Johns was terminated a few months later, apparently because Levert Kelly, a union organizer with underworld connections wanted to unionize the hotel staff and Johns and Kelly argued over the matter. Johns was replaced by Eddie Flagg, who was referred by Levert Kelly. Eddie Flagg had been a bellboy at the Ritz Hotel, located at Oakwood Boulevard and South Park.

Flagg had made quite a name for himself by "taking care" of the many musicians and show people who had stopped at the Ritz Hotel. The Ritz was primarily a theatrical establishment because the Grand Terrace Night Club was housed in the same building [before the Grand Terrace moved to 35th and Calumet Avenue.] The Ritz and the Grand Terrace were owned by Ed Fox.

Because of his popularity, Flagg was successful in persuading most of the residents in the Ritz to move to the DuSable Hotel with him.

Several months after the DuSable Hotel opened, Ben Cohen decided to put a cocktail lounge in the basement of the building. Charlie Cole, a Blatz Beer salesman, was approached by Ben Cohen who asked him to find someone to operate the lounge.


I had just caused Harry Fields and John Simmons [two famous tavern owners] to go in on the Playhouse Lounge on 50th and Grand Boulevard [prior to becoming South Parkway]. So I told them I had another spot for them. I said, "I have a place called the DuSable, it's turning over to Blacks and I don't know, but I think it's going to be a nice spot, something different."

Harry said, "Well, if it's so damm good, why don't you come in with us?" I said, "Well, I was going to give it to you two, but if that's the case, it can be a three-way deal." So that's how we opened up the DuSable Lounge.


We put entertainment in the lounge and different musicians would come out to jam. We were there 24 hours a day and that was a big factor. We had three bartenders. One worked from six in the morning until two in the afternoon, one from two in the afternoon until ten p.m. and one from ten p.m.until six a.m.

We sent Daddy O'Daylie to radio school. He learned how to tend bar right back there on our service bar. Ted Watson, who was a writer for the Defender, wrote all our publicity stories.

We took in big money. There were a lot of white people who came in. The frequent faces were from downtown as well as up north. The people who owned the Chez Paree always came out.We started gambling in the hotel on a Friday which didn't usually break up until Monday. We gave Jimmy Cooper a job on the door. He later won enough money in a gambling game to buy the Ritz Lounge. Al Benson was very popular back in those days. He came in the Club often. He would spend his money, gamble, and drink.

I think the reason that the DuSable and many other places flourished was due to the fact that prosperity came about because of World War II. At first, people were very frugal, they saved money because they had been used to rough times living through the depression. They were limited as to things they would buy. But back in 1944, everybody had money due to the war and they began to live much less frugally.


Cohen put the bar in the lower level of the hotel and all we had to do was buy some whiskey. We agreed to give him five percent of the gross sales—which he never did get because we never gave it to him. I got Vernon Rose, he was cooking at Morris' Eat Shop on east 47th Street, and I put him in the kitchen.

CLARK TERRY, musician:

When the DuSable Hotel turned over, it brought about a change in that community and that whole area. I was introduced to the DuSable area in my Navy days. That was in 1942 when I came to the Great Lakes Navy Base to be in an all Black Navy band. The DuSable used to be the hang out for most musicians and show people.

We navy men were sort of a new breed as far as the Black man was concerned, because prior to our enlistment, all Black people associated with the Navy were chief cooks, bottle washers, boot blacks and stokers—shoveling coal. When we came in, in 1942, that was the year a new program was inaugurated. When we received our graduation diplomas and our ratings, we wore them on our sleeve. To see a Black man in the United States Navy without a "C," which meant a cook or whatever menial chores they could be subjected to, well, it was just an oddity, and we literally took over the town.

The popular spot had been the Bacon's Casino, on 49th and Wabash. That used to be our headquarters because the USO was there. After our graduation in 1942, we spread out in all directions, and somehow we ended up at the DuSable. The "Du" was far more popular than anything in that area. It was a new thing for us, crossing into a new neighborhood. So, we flocked into it mostly for the sake of being in a new area.

It was absolutely the most fashionable bar on the South Side in those days. It was very chic, and that big circular bar in there, that was the new thing. Daddy-O Daylie worked as a bartender. He'd entertain everybody with his rhymes; he had a special something to say to everybody who came in.

BRENNON GLANTON, Clerk in Nate's Men's Wear on 39th and Cottage Grove Avenue:

The DuSable Hotel was a renaissance for the area because it represented a status thing to the young Blacks who wanted to imitate Blacks they admired because of their life style. When you got to the place where you could afford to take a date down to the DuSable Lounge where Lefty Bates and his trio was playing, you felt you were into something. The bartenders were very classy and the women would dress well to go down there to flirt with the bartenders.

Blacks began to move into the area and displaced the whites who moved out. It was really a brothel red light fast district for whites day and night. A few of the swift, sophisticated whites stayed over and mingled. The "Du" had the class ladies and the Palm Garden had the flea market ladies.

DAVE YOUNG, musician, sax:

All the top prostitutes lived in the DuSable Hotel. Although the prostitutes lived there, they were never allowed to operate in the place. Not in Eddie Flagg's hotel. He ran it pretty clean. The prostitutes were downstairs in the lounge. So, if I went upstairs to rent a room, it was okay because Flagg didn't rent to the prostitutes directly.

The prostitutes really made 39th Street a flourishing street. In fact, that's almost the way it is, wherever you go, with the "girls" around—in fact, wherever there's entertainment. That's what is happening now on the Near North Side. Prostitution is flourishing because it's supported by the intelligensia: by doctors, lawyers, judges, everybody who, for all visible purposes, would be against it.


Harry Fields and I left the DuSable in 1944 and we went out to the Pershing Hotel. We left because the building had become a fire hazard. The steps were wooden, and all the insides of the building were wooden. There were code violations everywhere. I thought it was wise to pull out and go to the Pershing Hotel which was a fireproof building. It was solid, it had six inches of concrete between each floor.

People began to go further south and further east. The neighborhood surrounding the DuSable started going down especially with street prostitution and dope so prevalent. The better element of people was all living out south. The DuSable had become nothing but a low-rate house of prostitution. Later, John Simmons, who bought Harry and I out, turned it over to "Cadillac" Bob. Bob renamed the lounge downstairs, "The Toast of The Town".

DUKE GROANER, musican:

"I was around 39th and Cottage Grove before Leonard Chess bought the Macombo Lounge. I don't remember who owned it before Chess. I used to work at the DuSable Lounge. I had a trio with Ernest Ashby on guitar and Robert Montgomery on piano. This was in 1945. The Floyd Smith Trio, with Floyd Smith, guitar, Bill Huff, piano, and Booker Collins, bass, followed us into the DuSable Lounge.

39th street was a sort of Mecca of entertainment then. There was the DuSable, the Macombo, the Palm Tavern with Oliver Coleman, drums, Silvester Hickman, bass and I've forgotten who was on piano now, but it was quite an area around there. There were two or three other little places that had piano players in and along 39th Street. Cleo Napier used to play there. She was a single pianist. She also worked at the DuSable as a single.

At the DuSable, Wilbur Hobbs was the main attraction. He used to make so much money playing torch tunes. He'd come out of the club with 50, 60 or 70 dollars a night in tips and that was a lot of money then. The average salary of the man on the street was about 15 or 20 dollars a week. However, in 1945, with the war going on, the money was a little bit greater.

The Macombo Lounge was something with Ike Day on Drums and Willie Jones, piano and later Bill Searcy played there with Tom Archia. For some time it was the spot. You weren't afraid of being ripped off, you just went and had a good time.

Tom Archia was there when Chess took over and he began to record all of us. We first recorded for Chess on the Aristocrat Label. That's when I made "Dragging My Heart Around." Horace Palm was the vocalist. Chess and two ladies picked out two tunes for us to do. One called "Blue Bird of Happiness" and then "Dragging My Heart Around." Sax Mallard and Tom Archia also recorded for him. Chess made a remark to someone that before it was over, he was going to own every Black musician out there, and put them on his label and he almost did that. I heard him make that remark.

Leonard was a nice guy. He was very aggressive and after he got a taste of the record business, he just couldn't turn it loose and he became a millionaire with it. His brother went right along with him, but Phil wasn't the man that Leonard was. At first Leonard just started the recording business for a little hobby but he had no idea that it would blossom into the moneymaker it did.

He still kept the Macombo although he wasn't paying the guys much money, but everybody was happy playing there for just a little or nothing. Everybody came through there. I remember one morning we were there and Buddy Rich came in. He had come to hear Ike Day. Buddy Rich came down to see him and so did Louie Bellson. They just shook their heads when they saw Ike playing the drums the way he did. He was just something else.

If you ever hung out with Ike you paid dues. Ike would borrow money from everybody. One of the last times I saw him, he wanted $3.00 and wanted me to hold his necktie. I said, "That's alright, just take the s--- $3.00." He never did come back.

Yes, there was a sort of cast system, as to who hung out and where. There was one class who hung in Leonard's Macombo and another class who hung in the DuSable Lounge. The gamblers and the big shots, so to speak, and people with more money hung at the DuSable, along with a lot of the entertainers who came to town like Ben Webster, Duke Ellington, and Coleman Hawkins. They all hung out over at the DuSable because most of them all lived at the Hotel. And the Lounge was right downstairs.

The prostitutes walked the street night and day and you could just sit in your car and watch them hustle tricks. A lot of the prostitutes hung out in the Macombo. The high class ones however were in the DuSable Lounge while others hung out in the Palm Garden Lounge east of the DuSable. There had to be quite a bit of payoff to the police for the ladies to be as open as they were because they couldn't operate as they did if somebody hadn't been paid off. There were not many Black cops around 39th and Cottage at that time.

I lived at 3809 Lake Park with Wild Bill Davis, the organist. The neighborhood was just beginning to change from white to Black. Across the street from the Palm Garden was the Morocco Hotel and it had a lounge with entertainment. "Cadillac" Bob took over the lounge, redecorated and renamed it the Flame Show Bar. Tiny Davis and her band and Anita O'Day were the opening acts. I worked at the Flame. Bob was a nice guy, in his way, but Bob's ideas were always higher than his bank book.

He built some fabulous places, or rather Dan Gaines built them and let him manage them. Bob always stayed in debt with the musicians. You never did get your money on time but you would finally get it. He had trouble with the musicians' union, but he always tried to provide a place for musicians to play. He just couldn't make the money."


I was in the army from 1943 to 1946 and my brother Leonard owned the 708 Club during that time. When I left for the army he had a liquor store at 5100 South State Street and 2971 South State. My father Jake owned a junk yard. When I got out of the army he owned the Macombo Lounge.

April of 1946 I went into the Macombo with Leonard. 39th Street was a fast life and a lot of money was spent there. After four months we got a band which included Tom Archia and every famous jazz musician came by. We never closed. We just pulled the blinds.

We got into the record business when Leonard met a lady that had the Aristocrat label. She was recording all white artists. They were not selling so when Leonard got into the business he started to record Black acts. Sax Mallard, Duke Groaner, Andrew Tibbs and others, including Muddy Waters and Sunnyland Slim.

Jack L. Cooper did not play our records. Al Benson played our records. He changed the music appetites of the radio listeners. I don't think Al lent Leonard any money but I could be mistaken. Al Benson was a tyrant. You had to admire him and hate him all at the same time. He could make a record.

Musicians were not taken advantage of by Leonard. They were treated like family. They had their car payments paid for and home mortagage payments paid, and never saw the payment books. They might come in and say maybe their girfriend was having a baby and needed to have some cash to cover medical expenses to avoid having their wives find out, and other problems. Whatever monies they received was advanced on their royalties.

John Burton was the company counsel. He recorded on his own. The bar business was rough. One business opportunity ran into another, from records to radio. If Leonard had lived, we would have gone into TV.


Jazz was one of the things that kept that area going. They had some of the best jazz and they had a variety of jazz all around the Drexel Square corner. There were commercial show bands, smooth slick trios, and hard driving quintets. They even had far-out playing jazz cats. There was even the blues when Jo-Jo came out. (Dr. Jo-Jo Adams was a blues singer who appeared at the Flame Lounge on East Oakwood Boulevard).

Leonard and Phil Chess, who owned the Macombo Lounge, were the ones who made the big step to capitalize off jazz by recording it. They also brought in different all-star groups. The Macombo would have Tom Archia, then Jug (Gene Ammons). Then they might bring in Eddie Chamblee. I never worked the North side in those days. I played in Chicago for almost ten years before I worked the North side. Wasn't anything there for me.

Eddie Chamblee:

I was making plenty of money on the south side. You could make a living playing music on the South side, working in your environment. You didn't have to go north.

There was more vice on that corner of 39th and Cottage Grove it was amazing. The Macombo was where most of the vice was. All the girls hung out at Jimmy's Palm Garden but all the heavy traffic, drugs, prostitution, everything else was at the Macombo. It was a heavy dope scene. A guy could just sit on a barstool and actually make his contact. Such as "two pills, a boy and a girl" (the boy was horse and the girl was cocaine), you could get a cap of each for a dollar and a quarter.

The dealers would have the stuff taped under the barstools. Certain guys had certain barstools. That was their stool from eight o'clock in evening till four o'clock in the morning. While they were sitting there, they might spend 20 or 30 dollars at the bar, but they might make $200 or $300 dealing. The police and everybody knew it. It was all sanctioned.

The police had to make a bust every now and then, but most of the busts were on the girls, the prostitutes. They never busted anybody in the Macombo. They were 90 percent white police. Most of the Black police were uniform police. There were a few Blacks that came out of the 48th Street Station, 48th amd Wabash Avenue. But all of the detectives were white. They got rich. A few of those police were really living. Later, I found out a few of them had bought homes out on Longwood Drive in Beverly Hills.

The Black police weren't allowed to get in to all that. When they did get in, it was on the tail end of everything that had been going on. If you were a Black detective, you still weren't equal to a white one, even though you might have more years. All orders came from the top, I believe. The vice couldn't operate unless the police department sanctioned it.

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