Jackson was resident performer at the De Luxe and Pekin Cafes in Chicago, although in his later years his voice and dexterity were impaired by disease. Although it has been cited by some as syphilis, the diagnosis at the time of his death was the more likely cirrhosis of the liver which had been progressing for years, in addition to chronic epilepsy. His friends knew that his health was suffering and they held a benefit for him on February 17, 1921, calling it the "All Star Tony Jackson Testimonial" and raising $325 for Jackson. He died in Chicago on April 20, 1921.