The English international had made a name for himself during his stint with the Gunners.
At the age of 19, he struggled to pay fines for traffic offence and was sentenced to 14 days in prison, something which he now claims gave him the power and passion to succeed in football.
The ever-controversial former English international was jailed for six months in May 2008 for attacking a man in Liverpool city centre.
The then Newcastle player was caught on CCTV kicking and punching his victim to the ground while being drunk. He was also given a four-month suspended sentence in the same month for relentlessly attacking Manchester City team-mate Dabo in a training ground incident in May 2007.
The Arsenal legend spent time behind bars for drunken driving in 1990 and spent 57 days inside. He was found to be 27 times over the permissible limit after knocking his car.
But his prison term hardly influenced his playing time and he was soon a regular in the Gunners team once more.
Then an Arsenal youngster, Pennant paid the price for crashing his Mercedes into a lamp post while under the influence of alcohol in 2005.
He was given a three-month sentence but just served 30 days behind bars and was released on parole, immediately signing for Birmingham.