He may not have been there for it personally, but Garrett would be hard-pressed to not know about The Prague Incident. To this very day, his old contacts are still trying to work out what the hell actually happened that night, as if 'Jailbreak was involved' isn't already a sufficient enough explanation for everything. It is entirely possible that he knows a little more about what happened than most, but he's not known for his habit of outing his fellow associates.
...which brings him to the realisation that none of said associates are actually set up out here, and that for all of his talents, he is going to be well and truly alone in this place if he doesn't start swallowing his pride real fast. It's certainly not the worst price to pay for a free coffee and a shot at reconnecting with a powerful ally, even if she can be somewhat obnoxious to deal with.

"...if you're buying, there's a dainty little café back there. Off the beaten path, decently concealed, looks like the decorator read too many nursery rhymes as a kid..."

In a manner of speaking, Garrett trusts Jailbreak. Specifically, he trusts Jailbreak in the same way you trust a honey bee to leave you alone unless you piss it off. As far as he's concerned, she the most upfront and honest professional criminal in the business, so when she offers you a drink, she's just offering you a drink. Any subsequent Prague Incidents that occur as a result of her general vicinity tend to just happen regardless of what's already happening, though it's up for debate how many of them she actually causes on purpose.
(Garrett's current estimate is 60%. It'd probably be a lot higher if he had spent more time around her.)