Laptop holding Trump Tower floor plans, Hillary Clinton email investigation info stolen from Secret

[ColemanMaskell]

92. It sounds like the thief knew the agent, or at least had been observing the agent.

Also it sounds like the agent is just incompetent, a trait we're seeing a lot in public life these days.
The thief may have observed, or become acquainted with, any number of agents until finding one careless and incompetent enough to leave a laptop in the car. The thief does not need to know the contents of the laptop to know that an SS laptop is likely to be valuable, either to hold for ransom or to sell to interested third parties.

The fact that the thief had the driver go right up to the driveway, rather than leaving the car a few blocks away, hints that they didn't want to be seen in the area any longer than absolutely necessary. If a friend of the agent, they could be afraid of being identified by a neighbor. Or they might simply have been afraid of being caught on security cameras. The thief must have had fear of being recognized, for whatever reason.

Could be the agent's boyfriend, or ex-boyfriend, husband, or some other close person who would know that particular agent well enough to be aware that she was careless with her laptop. Could be the agent herself is actually a very careful agent normally, and she was in on the deal and left the laptop deliberately, then reported it stolen.

As for "how would it be known that the thief got to the agent's driveway by Uber?" they actually only said the thief was dropped off and that the car might have been an Uber. If they know the thief was dropped off, then presumably either there was a witness or it was caught on a security camera.