Connor's friends have seen him get picked up from school by a wide variety of people, if he's not walking home or staying overnight with them that day. Usually, it's a woman with striking features, Ziio, his mothers, who stands by the school gates and who's face lights up immediately when she sees her boy. She would greet Connor's friends warmly, maybe chat with them a bit, before they both walk home, chatting idly in their native tongue.
Another person whom they saw was Connor's Aunt Jennifer, who picked him up whenever Ziio, or Haytham were too busy. She took a liking to Elise whom would chat with her when waiting on Connor, while she was waiting for Arno to finish his class as well. Jennifer would never let her brother know, but she loved picking Connor up, having no children of her own and loving his gentle nature. She treasured her time with him, so she would usually go with him to get food (healthy of course) or go to the park.
There was one man who very rarely picked Connor up, his dark hair pulled back in a small pony tail, usually checking messages on his phone. Shay would be leaning against a large black car, looking up every now and then to see if he could spot the boy. Arno, for no reason he could fathom, took an instant disliking to him whenever he saw him, so would Achilles, Connor's teacher, whenever they talked after class, even though he felt more melancholy than anger. Connor's face would always slightly drop at the sight of him, knowing that Shay only did the picking up whenever Haytham promised he would but suddenly couldn't make it. Shay would feel bad, offering a sympathetic smile to the boy and would try to make it up to him, allowing him to grab food (unhealthy if he wanted, but only if he could snag a few chips as well). Connor didn't really mind Shay, he was nice, tried to be friendly to his friends whenever they walked with him, he was funny and would tell embarrassing stories of Charles Lee when driving, such as the time Shay convinced him that crocks with socks was the height of fashion and would impress Haytham. It was just what he stood for, which Connor hated. He stood for his father's broken promises to his son, not being there and sending someone else, not thinking about his son wanting to see him once in a while.
Then there were the times they saw a sleek business car. At first they didn't associate it with Connor, so when he stopped right in front of it, they didn't know what to think. Haytham never got out the car, just sat in the driver's seat, answering messages on his phone, scheduling meetings with De Sable, Torres, Borgia, Starrick, endless names which meant nothing to Connor. Haytham would be so engrossed that his son would lightly tap his knuckles on the window so he could unlock the door. Connor's father would offer his friends a small nod before driving off. Things would always start off well, his father actually setting his phone aside to talk to his son, chatting about school, plans for the weekend, about getting Connor a dog (he'd been begging for one since he was young with Haytham masterfully always avoiding the subject) until his phone would light up. Connor would see the name on the dashboard, CL, Charles Lee, and his small smile would utterly disappear. No matter if Haytham answered to call to his subordinate or not, by the time they reach home, they'd either be arguing or sitting in angry silence. Ziio would always beg the two of them to spend more time with each other, avoid touchy subjects, become closer but Charles Lee would always be the split in their relationship, a chasm that seems unfix-able. Ezio even, whenever Connor ranted about him, had an epiphany that Charles Lee would spy on him and his father and whenever they seemed to finally get along, he'd call to see if he could ruin it. Altair and Evie promptly buried their faces in their hands, utterly done with Italian, while Jacob heartily backed him up. Arno just rolled his eyes and Aveline advised Connor to talk it out with his father.
Now, one day, they saw someone pick Connor up, they've never seen before. They had walked out the gates and no one was there. The boy scanned the road, eyebrows furrowed before his face broke into a wide smile and he advised his friends to stands back from the curb. A few seconds later, a beat up pick-up truck, crusted with sand and littered with dents swung haphazardly onto the curb, loud music blasting. Edward Kenway, his grayed hair tucked into his usual ponytail, his skin tanned from a lifetime on the sea, in the sun, laughter lines prominent on his face, jumped out and immediately embraced his grandson. Connor wished he took a picture of his friends, Altair had never looked so gobsmacked, that this beach bum was related to Connor, was related to Haytham. The moment only got better when Professor Adewale walked out of the school, smiled and embraced Edward like they were long-lost brother and immediately reminisced about the good old days. Ezio liked him on sight and Jacob was dying to go home and get Evie to help him go through his family records, to see if he could be related to this awesome grandpa.
Calling Edward his ride back home wouldn't be apt. Connor and his gramps wouldn't be home for hours, the senior Kenway taking him out to eat at the beach, talking excessively, driving around town, teaching Connor how to hunt Sharks, prank calling Charles Lee's office with appointments that will never happen, letting his grandson meet his buddies, Ed Teach, Mary, Benjamin, Stede, Vane, even Calico Jack, which is an unforgettable experience in itself.
They'd return home after dark, Haytham out his mind with worry, while Ziio being quite relaxed about the situation, as she phoned Edward up, begging him to see his grandson, telling him Connor's school and when it ended, to ignore the boundaries Haytham tried to set between his alcoholic father and his impressionable son. Edward, who missed his family, who wanted to see his grandson, agreed immediately. Connor had only met him a few times before, like when at his grandma's funeral, when Edward had ambushed Haytham and begged to let him see his family, when Edward had actually shown up in person on Connor's birthday to quickly slip him a present, wish him happy birthday and slink off before Haytham showed up. Connor still wore the shark tooth necklace everyday, underneath his clothes.
Edward would happily take the blame, could take Haytham's yelling, even enjoying the panicked tone in his voice, which betrayed how much he worried about his son. Connor had been sent to bed by Ziio with a small grin and a promise that everything would work out. He woke up in the morning and knew something had happened while he slept, as suddenly there was an arrangement, allowing Edward to pick Connor up on Fridays and spend a few hours with him.
Connor would always treasure those Fridays, especially the time when Edward allowed his friends, everyone, Altair, Ezio, Arno, Aveline, Jacob and Evie to come with them and spend a Friday with Edward's buddies, the kids spending time with the retired Pirates, even maybe committing a few slightly-illegal acts under the watchful eye of Mary.
But anyway, that's who picks Connor up from school.