Several websites I've come across state "чалый" as a synonym of "рецидивист", but I haven't been able to find any definitions of чалый that would suggest it's synonymous with рецидивист.
Are they synonymous? Is one a slang word for another?
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Чалиться is a slang word meaning, in the wider sense, "be stuck somewhere, be forced to waste time": чалиться на заводе, чалиться в деревне etc.
In the narrower sense, чалиться means "to do one's time" (as in the prison). This might be used as чалиться на шконке ("do the time on the prison bunk bed") or чалиться на зоне ("do one's time in the corrective colony") or similar.
The person who is known to have been engaged in this activity might be called чалый.
This is an active participle from this verb, using an old pattern with -л- which is not productive in Russian anymore.