"It takes a thief to catch a thief."
I don't know who coined it, but the saying seems generally accepted as true, and highlights a commonly perceived obstacle in law enforcement, that a law abiding officer -- which, I must assume, is one reason to have a robot police force, so ideally human sin and error are minimized -- however skilled, simply does have a criminal mindset. Professional criminals perceive the entire world differently, so adaption will likely be in unexpected, criminally brilliant ways.
However, there are also criminals who inadvertently outwit the law, and by unconscious heuristics subvert the system, and not by being very intelligent, but intuitively or by plain luck.
For example, if robot/people cops only use the newest and best technology, and the fortunate criminal keeps using his or her legacy system for communication, either by chance or some belief that it's 'lucky,' such a criminal would be very difficult to catch, especially in an advanced society. So long as no major blunders were made at least. Another way of saying this is, what if it never occurs to cops in a future society to read snail mail?
I think two things from Murphy's Law of Combat are parallel to the criminal mindset which cause untold trouble to law enforcement, which make criminals difficult to handle, regardless of technology:
- If it's stupid but works, it isn't stupid.
- Professional are predictable, the world is filled with dangerous amateurs.
In other words, however numerous and skilled the hounds, they never see the world as a fox.
Starting with a precept that criminals will cleverly hack and subvert a system, using the Man's technology against Him is a rather academic view of people whom generally aren't. Practicality rules. And using tech in any way would tend to give an edge to law enforcement, not the other way around. The creator of technology always knows it better than a user, even a smart one. The Man makes/funds tech, criminals will almost always just be users who found a crack in the wall.
And anyway, technology aside, as I understand it, according to Mitnick, the best hacks have always been via social engineering, not device exploitation, though it helps sometimes.
For reference on your subject, check out the original Stainless Steel Rat trilogy by Harry Harrison. The series explores the topic of future criminals.