Allegra, a self-professed Apple fanboy, is notorious for his JailbreakMe packages that allow iPhone owners to break through Apple's fortress-like software. Then Apple would patch things up with an update, only to have their defenses breached in another way. So the cat-and-mouse game went... until now.
In truth, Allegra's being hired has probably been in the works for awhile. What better way to stop a crime than to hire the criminal? It works in the movies, anyway. And they've done it before, having hired MobileNotifier's Peter Hajas shortly before they announced iOS 5.