MALA i have no idea why this SUDDENLY occurred to me just now, but we could totally say that Link and Jack should have already met?!?! in the three years since he woke up, Jack has pretty much just been wandering around from place to place on his own totally fruitless search, and he circled back around to cities now and then just to listen for news and play with kids so like

he would totally have come to Citadel several times over the years and he would have loved to hang out with Link???