Rev. Harold E. Bailey and Probation Challenge celebrate 31 years of helping troubled youth

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It’s a “vision” that keeps on giving and a great legacy for the annals of history


 World’s famous “Impressions” and Gospel Singer Calvin Bridges will provide entertainment for Probation Challenges’ Annual event on the International Stage, Friday, August 20, 2010, at the Condesa del Mar 


By Juanita Bratcher


Chicago, IL – He calls them “My sons and daughters”, sort of like a term of endearment. They are young people who had minor scrapes with the law, found themselves bottled up within the criminal justice system, and subsequently became clients of the Probation Challenge program.

They are former and current clients. And more often than not, they came to the Probation Challenge program through a court-mandated system put into place by the Illinois State Legislature.

                     See the full August 14, 2010 interview 

               with Rev. Harold E. Bailey on video stream, One on One

                    television, located  on the right side Cover Page of  

                    CopyLine Click on “On Demand” 

Rev. Harold E. Bailey, Founder & President of Probation Challenge and a former Cook County Adult Probation Officer, served in the courtroom of the late Judge R. Eugene Pincham. He started the Probation Challenge program some 31 years ago.

Probation Challenge is the first program of its kind in the country, and during its 31 years of existence has managed to help thousands and thousands of youth, sending them back into society as meaningful and productive citizens – something he enjoys doing, he acknowledged in a recent interview with CopyLine magazine. Many of his clients have gone on to various colleges and universities.

Since its inception, the program has had its problems and setbacks. In an August 28, 2009 article in CopyLine magazine, “God is Right, Somebody’s Wrong”, by Rev. Bailey, he talked about some of those problems and of physical threats made against him.

“Since the inception of the Probation Challenge concept in January 1979, I’ve had more than mere opposition to the program’s worth. I’ve had physical threats made on my life for seeking to educate young men and women filtering through the criminal just-us system,” Bailey said.

 For 27 years, the Probation Challenge program was located on the campus of Olive-Harvey College in Chicago. However, City Colleges of Chicago, owner of the facility, evicted the program from the premises, but continued to use the Probation Challenge name.

Bailey filed a lawsuit against City Colleges of Chicago after being “illegally evicted” from City Colleges’ Olive-Harvey campus, and their continued use “to make merchandise from the Probation Challenge name without mention of Bailey, founder of the organization.” 

On August 14, 2009, the Circuit Court of Cook County ordered that Probation Challenge, an Illinois corporation, incorporated on September 24, 1980, “shall have exclusive use of the name “Probation Challenge”.

It further stated that, “City Colleges of Chicago and Olive-Harvey College, their agents, assignees, representatives and successors shall discontinue the use of the name “Probation Challenge”, effective immediately.


Focusing on his 35 years overall working with youth and 31 years of Probation Challenge, Bailey said: I know how they (youth) think. I know how they tick…and it hurts to see my sons and daughters out on the street not getting the love and concern that they’re entitled to,” since his program was scaled back after the eviction from Olive-Harvey premises.


“They know me. They know I don’t lie to them. They know that I tell them the hardcore truth…truth travels. Truth does travel. It spreads, but lies fly. Truth has to stand up. And truth should stand up more than ever before; because our young people are suffering.”

Probation Challenge will hold its 31st Annual “Portrait of Achievers” Awards and its popular “Show of Shows” entertainment extravaganza on Friday, August 20, 2010, at the Condesa del Mar, 12220 South Cicero Ave,, beginning at 7 p.m.

This year’s award recipients are Marvin Forbish and Clarence Glover. The world’s famous “Impressions” and Gospel Singer Calvin Bridges will provide entertainment on the International Stage.

For more information and reservations, call (773) 978-3706. 


Although Bailey has dedicated 35 years to helping young people, he has no intentions of calling it quits. He will not walk away from his vision that has helped so many.


“We must have a spiritual and moral responsibility to these young folks,” he said. “A lot of this stuff going on is orchestrated, contrived and coming from the pits of hell. I was watching TV and saw two of my former clients had been arrested. It hurt me to see it. It viciously hurt me to see that they had gone back to old habits.”                                                                                         

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