Chicagoans Bid Farewell To Joseph "Joe" Caldwell Sr.

Owner of TailoRite Cleaners

Joseph Caldwell was born with the help of a midwife on December 19, 1932, to Florence Wilson Walker and Joe Nathan Caldwell. Born and raised in Marvel, Arkansas. Joseph spent his early years on the Farm outside of Marvel learning from his grandparents. His grandmother called him "Little Bo Peep" as she rocked him to sleep, reciting the nursery rhyme. The nickname stuck. His grandfather had a huge impact on his life, teaching him how to hunt, the value of education, and the importance of character. A few months later, his first cousin, Stella, also moved in with his grandparents. Stella was like a sister to him. 

At an early age, he accepted Christ and was baptized at New Light Baptist Church in Marvel. The one-room church doubled as his elementary school. 

His mother, a sharecropper, first introduced him to picking cotton when he was 4 years old. At first, she dragged him through the field on her sack, and then she made him his own sack with a sash. His small hands were quick, and he was a great asset. So much so that when he was five, her sister, his aunt, Julie Robinson (OC), asked that he move with them to Osceola, Arkansas to help with the picking of her cotton. His Uncle OC ran a Roadhouse where Joseph learned to roll dice, Horn Dice, Pad Roll, Soft Dice, Lock Dice. In fact, he had dice in his pocket every day and would shoot dice and win at 7 and 8 years old. He did not stop gambling until he came out of the military.

He sharecropped with his aunt from the age of 5 until the age of 14. He picked 300 to 400 pounds a day but ran back to his mother, who lived on an adjacent farm, because his aunt would not give him 35 cents for a haircut. His aunt shot at him as he ran away. He credits his aunt for giving him his work ethic and teaching him responsibility. 

He continued to sharecrop with his mother while he attended Tate High School, played baseball, and boxed. To attend school and help his mother economically, he picked cotton by moonlight, making Sl.50 per 100 pounds of cotton and $15 per bale of seeds plus free room and board. It was enough for him to assist her and save. At age 16, he knew that he needed a better life, so he wrote to his father and asked him to come to Chicago. 

He got on the train to Chicago in his green suit, tin suitcase, and $85, quite a stash at that time. When leaving Helena, Arkansas, he heard a passenger say he was on his way to Chicago. Deathly afraid, he followed that man all the way! There were two stops in Chicago, the first was 63rd and Dorchester, an area that had not been integrated. and he waited for the second stop. 

He often remarked that he did not know what would have happened had he got off at the first stop. When he got off the train. his cousin met him at the train station. He asked his cousin how he knew it was him, he said because "you were the countriest man on the train!" His cousin showed him the handwritten letter that he had sent to his father. That cousin, Charles Wesley Caldwell, "Little C". looked out for him from that day forward. 

Upon arriving in Chicago, his father could not take care of him, so he lived with his Uncle Charles Caldwell and his family on the West Side of Chicago. He slept on a couch and worked at a mattress factory at night while he continued his education at Wells High School. His uncle and aunt assured him that they would always make room for him. 

In 1950, at the age of 17, his Aunt Julie's husband, his Uncle OC, got gravely ill, and she asked that he return to Arkansas to help her through another cotton-picking season. Though he had run away from her years earlier, he still returned to assist. 

In 1951 he returned to Chicago, bringing his childhood friend, Richard Phillips. America had just instituted the draft for the Korean War.

Richard was drafted into the A1my in June 1951. He now had a dilemma; he could not afford his rent by himself. His Uncle Charles, impressed with his work ethic and quick wit encouraged him to join the Air Force. 

He passed the admission test and went through basic training at Sampson Airforce Base, was stationed at Lockbourne Air Force Base, went to Cheyene, Wyoming for technical training as a Supply Technician, got deployed to Casablanca, Morocco in North Africa where he earned the rank of Corporal. He was honorably discharged in 1954 from Camp Gilmore. 

When he came out of service in 1954, Richard had been back in Chicago for two years. Joseph and Richard moved into an apartment on 40th and State. It was next door to Robert's Temple, where they held the funeral for Emmitt Till. He recalls witnessing the funeral procession from his bedroom window. It was a scene that underscored Joseph's decision to migrate north away from southern landowners. 

He convinced Richard that they needed to takeadvantage of the GI bill. Joseph wanted to go into business, so he started shopping for a trade school. They happened into tailoring because Richard could not qualify for tool and dye making! 

In 1955, they enrolled in an 18-month course at the Metropolitan School of Tailoring where they earned the rank of Master Custom Tailor. So impressed with his talent and character, the owner of the school, Celious Henderson. not only became his mentor but his business partner, along with Richard Phillips and Esley Williams. Upon graduation in 1956, they opened Tailorite Complete Clothing Care Company. 

Joseph was also a man who liked to have a good time. In 1956, he and his Metropolitan classmates started the Gentleman's Tailor Club. They threw parties to raise money for various charities. In fact, it was that group that first brought Dick Gregory to Chicago to perform. Members included his lifelong friends Henry Johnson, Sidney Cunningham, Esley Williams, Richard Phillips, Robert Johnson, B Johnson, Henry Mitchell, and Johnny Johnson. All the club members were trained tailors  except for one, Robert Johnson. Sidney Cunningham (Sadie) brought Robert Johnson  (Oristine) into the group  because they were dating two sisters whom they eventually married. Sidney introduced Joseph to his sister-in-law, Barbara Jean King, in 1957, and they married in 1958. "Uncle Sidney" remained one of Joseph's closest friends and confidants until his death. 

Joseph credits comedian/activist Dick Gregory with his and Barba-ra's first marital argument. Dick had performed at the Esquire, and his show ended at 2 am. They decided to go to the next spot in Robbins that had a 4 am license, but it never closed. When Joseph saw sunlight, he jumped up, leaving Dick Gregory at the club, and ran home. He snuck in at dawn and tried to set the alarm back two hours, but Barbara was wide awake! 

The couple rented apartments at 6964 S. Parnell and 900 West Marquette Road 2nd floor, before buying their first property in 1964, a two-flat at 8137 South Green for $26,ooo. It was the first thing either of them had ever owned. 

In 1959, his cousin Stella moved to Chicago after her husband was killed in Marvel, Arkansas, by southern landowners. She did not know how to contact her cousin Joseph. There was a bar called the Longest Bar where people from Arkansas would frequent. She went every day until she found someone who knew her Cousin Joseph. Growing up Stella made doll clothes; it was enough. She went to work for Tailorite in 1960, where they worked closely until her death. Tailorite has employed many family members: Wille Mae Wilson, Lee Robinson, Charles Robinson, Vernon Caldwell, Joseph Caldwell Jr., Kevin Fleming Jr., Karen Caldwell, Christoria King, Morgan Charles, Payton Charles, Veta Caldwell Charles, Benjamin McKinney and Barbara Caldwell. Outside of his wife and children, Charles Robinson and Stella Wilbon have been his most ardent supporters. 

Recognizing that to run a business it was not enough to be a master craftsman, in 1959 he continued his education studying business at the Illinois Institute of Technology. In 1960, he completed his education at Marion Business College.

Tailorite is a proven business concept of both retail and commercial clothing care, servicing some of Chicago's most influential leaders, loyal community members and large Chicago institutions to include the Chicago White Sox, the Chicago Bulls, United Airlines, The Museum of Science and Industry, Trinity Unity Church of Christ, the Chicago and Metropolitan Chapters of Delta Sigma Theta Sorority Incorporated, the Daley Center, Chicago City Hall, Netflix, the Judge Mathis Show, Disney Quest, Harold Washington College, Chicago Public Library, and Israel Church of God; just to name a few. Now in its 69th year his legacy continues.  

He is survived by his wife Barbara Caldwell, four children Vernon Caldwell, Karen Caldwell (Kevin Fleming), Veta Caldwell Charles and Joseph Caldwell Jr.; nine grandchildren LaToya Dixon, Monee Franklin, Jeremy Caldwell, Kevin Fleming Jr., Lauren Caldwell, Kyle Fleming, Morgan Charles, Payton Charles and Joseph Cald-well III; beloved nephew Johnny Washington (Sharon); cousin Flora Robinson; and five siblings Charles Robinson, Lee Robinson (Genevieve), Benjamin McKinney, Francis McKinney Johnson (Frank) and Antionette Caldwell (Thomas). He also leaves behind a host of nieces, nephews, cousins, and friends to cherish his memory.



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