Tommy Gordan, a self-absorbed criminal, believes he's above the law and entitled to special treatment due to his connections. His lawyer, Ed Crowley, has consistently gotten him off the hook, but Tommy's girlfriend, Kay Manners, is increasingly uncomfortable with his criminal activity. Despite being caught, charged, and sentenced to Sing Sing, Tommy expects Crowley to secure his release and special privileges, including not having to do what he doesn't want to do and wearing his expensive clothes. However, Warden Walter Long has a different plan, focusing on true rehabilitation rather than coddling inmates. As Tommy begins to change, Warden Long allows him unescorted day leave to visit Kay after she's injured in an accident. But when Tommy learns Crowley was involved in the altercation, his plans may take a drastic turn as he contemplates revenge.
Castle on the Hudson
A once-tough mobster finds a new path after being imprisoned, with the help of a wise and compassionate warden who guides him towards redemption.