Joseph Caldwell Sr., beloved tailor for Chicago White Sox, dies at 92

Wednesday, October 22, 2025
CHICAGO (WLS) -- Joseph Caldwell Sr. was known as a tailor and trailblazer, who helped countless people look their best.



He died last Tuesday at the age of 92.

He was the pioneering business owner of TailoRite Cleaners and a fixture on Chicago's South Side for nearly seven decades.

Joseph Caldwell Sr. was known as a tailor and trailblazer, who helped countless people look their best.



Caldwell was the tailor for the Chicago White Sox and prominent city leaders.



A celebration of life will be held on Saturday, Oct. 25 at House of Hope on 114th Street at 9 a.m.
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