Tail Dragger at Cook County Jail (Photos by Jon Sall)

James Yancy “Tail Dragger” Jones was confronted by fellow blues musician Bennie “Boston Blackie” Houston in the early morning hours of July 11, 1993 at the Delta Fish Market at Jackson and Kedzie. They had an ongoing dispute about payment at that year’s Chicago Blues
Festival. Blackie had threatened Tail Dragger with a knife and according to 1993 court records, Tail Dragger testified that he shot Blackie in self defense. Blackie was hit  in the left eye.

Blackie, 49, died on the scene.

Tail Dragger was convicted of second-degree murder. He served 17 months and three days of a four-year sentence. Tail Dragger first went to Cook County Jail for processing before being dispatched to a minimum security prison in downstate Lincoln.

Tail Dragger, 77, returned to the scene of the time on May 2 when he appeared in a rare concert in the gymnasium of the Mental Health Transition Center at Cook County Jail, 26th and California. Blues legend B.B. King recorded the hit “Live in Cook County Jail” in 1970. But King was never imprisoned like Tail Dragger.

The gig was recorded for a Tail Dragger documentary. There was no other media besides this reporter and a photographer. About 150 inmates attended the show. Many entered the arena handcuffed two by two. They all wore beige DOC jump suits. The highlight of the hour-long
set was when Tail Dragger removed his trademark cowboy hat and sang his hit “My Head is Bald.” The bald and lean blues singer walked towards inmates who sat on bleachers. Tail Dragger eyed a female prison guard and and serenaded her eye to eye. The audience applauded and howled in playful delight. It was a timeless memory in a place where time moves slow.

Tail Dragger wore shiny black snake eel skin cowboy boots he bought at Alcala’s Western Wear in West Town. He was accompanied by long time compatriot Martin Lang on harmonica, Kevin Shanahan on guitar, James Murphy on bass and Dean Haas on drums. Tail Dragger has released four albums, all of them since he left prison. Chess and Sun Records legend Howlin’ Wolf pinned the “Tail Dragger” name on his guitarist because he was always late for gigs.

Christopher “C.J.” Jacobs is program manager for the Cook County Sheriff’s Office Dept. of Corrections. He tries to books quarterly shows at the jail. Past performers have included the blues band Mississippi Heat and the Chicago rock band Where’s Fernando. “The music is therapeutic, visual and about communication,” Jacobs said before the show. Tail Dragger will appear in a more public setting at 5:30 p.m. June 8 at the Chicago Blues Festival’s Front Porch Stage.

Tail Dragger and his friend/harp player Martin Lang (Jon Sall photo)

Tail Dragger’s story is filled with colorful Chicago history.

His attorney was the iconic public-interest lawyer Marshall Patner. Patner had represented clients as diverse as  Jeff Fort and the Blackstone […]