Davos arrived a year into the siege, so it must have been towards the end of the war.
You know, I want to know the story of how he got that job. I want to know it so bad.
Because someone had to actually track down a badass smuggler, which if they could do reliably you’d think he’d have already been in gaol, and then they had to make it worth his while to sneak past the entire frickin’ Redwyne fleet, which is a MUCH DIFFERENT proposition than dodging customs patrols and maybe bribing some inspectors. Did they threaten him? Or just promise him the knighthood and wealth that he eventually received and Davos was thinking “I’m married and have kids now, I need to think about my future” and was like “okay deal.”
I just love the idea of Jon Arryn reluctantly sending a bird to his less-than-couth Gulltown Arryn cousins and being all “we need a someone to sneak into Storm’s End, you guys run the biggest port in the Vale, who can you find for me?” and them being all “Well, nobody legitimate. Legitimate merchant captains aren’t in the habit of running blockades. We’ll need a smuggler.” And Jon is like “UGH FINE whatever, make any deals with some douchebag who brags about how he makes the Kessel run in less than twelve parsecs you have to, just get them onions to Stannis” and it turns out Davos is just in the right place at the right time to get dragooned.
It wasn’t a hired job; Davos had a load of onions and whatnot and decided to break the siege to get a better deal.