But Outley came back.
Outley, who died May 17 at the age of 87, always believed that it was through divine intervention that his sentence was set at 10 years, not life, and he served seven.
When he was released from prison in 1962, his life course took an about-face. He went to school, earned a bachelor's degree from Goshen College in Indiana, a master's in social work from the University of Pennsylvania and ultimately a doctorate from Union Institute and University of Cincinnati.
The incorrigible, drug-addicted jailbird had become "Doc." The people he inspired to kick drugs had a watchword: "If Doc can do it, so can I."
After working with other agencies in the city, Outley founded SELF, Inc., in 1982. It became a renowned drug-and-alcohol outpatient treatment program with homeless shelters and treatment centers all over the city.
As Outley once told a group of homeless people, "You're not dumb; you're sitting in dumb seats. There are no dumb drug addicts. We had to be smart to stay alive out there on the streets. We just made a lot of dumb decisions.
"But we're made in the image of God with infinite potential. We have to learn to change the way we think, feel and behave in order to rebuild our lives."
Although Outley retired from SELF in 2005 and from the board in April 2012, the operation is still going strong, thanks to people like W. Wilson Goode Sr., Philadelphia mayor from 1984 to 1992, who worked with Outley over the years and has made a return trip to chair the SELF board and act as a volunteer CEO.
"He was a passionate guy who believed that everyone can overcome whatever issues they have and achieve great things in their lives," said Goode, who first served as SELF chairman in 1993.
"He always said he was 'exhibit one,' how he was able to overcome drugs and alcohol and jail and come back to work 30 years to help people achieve."
"The impact of the program has been immense," Goode wrote in an obituary for Outley. "Countless lives have been saved from addiction, crime and homelessness.
"There are literally thousands of SELF, Inc. graduates who have used Doc as a role model to rebuild their lives and become productive members of society again."
Outley wasn't the kind of crusader who spent much time in an office. He was out in the streets, confronting the homeless and the addicts and not always using gentle language. He was a devout practitioner of "tough love," and he didn't take any abuse from his potential clients.
Dave Davies, writing in the Daily News in 1996, recounted how he saw Outley talking with homeless men in a subway encampment at 13th and Market streets.
"He talked about rebuilding their belief in themselves," Davies wrote, "and said that once they had 'some principles' in their lives, the other things - a job, a car and a house - would come."
At the height of his "Clean and Sober" campaign, Outley had about 60 support counselors working with him - mostly former addicts who once lived on the streets - and ran regular group sessions at an intake shelter at Broad Street and RidgeAvenue and at Outley House, a residence for some 200 formerly homeless drug addicts in West Philadelphia. He also ran sessions at seven other large city shelters and at four group homes.
Outley was born a sharecropper in Alief, Texas, and grew up in Galveston, where his life of crime began. When he retired, he returned to Galveston. He died there of complications of myelodysplastic syndrome, a blood disease.
"He wanted everything for us," said his daughter, Astra Outley. "He wanted nothing more than that his daughters would be happy. He loved being with his family. Anything we wanted was ours."
Sylvester Outley lived in Overbrook Farms when he was in Philadelphia. Astra and her sister, Sylvia, attended Westtown Friends School.
Besides his daughters, he is survived by a sister, Lucille Crayton; his companion, Cecile Pridgen; and four grandsons.
Services: Memorial services in Galveston and Philadelphia are being planned.