Recruiting the Criminal: There are those who wonder about the existence of crime (actual crime, not merely the assortment of smugglers and people like the Eldinimieuthunimis who no-one locally would consider to be engaged in real crime) in Imperial and near-Imperial space. Surely the Transcend should be able to stamp that sort of thing out completely, not just near-completely? (Well, no, for reasons which among other things, involve showing some respect for free will.) Other people also point to the influence of one of the more morally gray of the eikones, Éadínah, the Princess of Shadows, eikone of night, darkness, subtlety, deeply-laid plans, and some would indeed say organized crime, or with a roll of the eyes point out the way in which all too many Imperials will look at the Gentleman Thief or the Classy Cat Burglar and permit their respect for talent, skill and sheer awesomeness to outweigh, albeit not overpower, their sense of moral outrage.
And, while those are most of the reasons, there is also the fact that various agencies – from the Fifth Directorate through more well-known parts of ISS, certain private agencies and even, indeed, some parts of official law enforcement – find having people like Mass Effect‘s Kasumi Goto, the Leverage team, etc., around to call on for those skills that they don’t teach in academia extremely useful.
(Nor, indeed, are they particularly shy about occasionally recruiting out of the justice system, when they can, with the promise of challenging work, an excellent benefits package, and the opportunity to keep any unconsidered trifles one might pick up along the way…)