Since having 'talked' to Pitch, Jack had been thinking about him a lot. His story about why he had chosen to attack the Guardians after so long, though possibly a complete lie, was quite touching.
Jack had talked North into telling him about Pitch's past shortly after they had defeated him last Easter, and was truly baffled. All the good that had been Kozmotis Pitchner had long since been destroyed by fearlings. There was no humanity left in him...
Right?
Or was there something left?
Really, after being far more alone than Jack had been for more than twice as long as Jack had been alive, Jack couldn't believe that Pitch was still sane at all. So to still have some human goodness in him... He had to find out.
After spending forever thinking up ideas on what he could do (really, it had taken only a few hours), Jack settled on a plan. It was simple, and he was positive it would work.
All Jack had to do was drop in and bug Pitch on a nearly-daily basis. He could keep on eye on Pitch, in case he tried to take over the world again, and learn more about the creepy, ancient spirit. And as much as he was certain Pitch would deny it, Pitch could probably use the company. If Jack were in his situation, he knew that company- even the company of his archenemy- would do him some good.
So, with a devilish smirk, Jack tumbled through the air toward the ground, spiraling around, before calling to Wind to take him to Burgess.
Jack had no idea what he was getting himself into by starting this: Both very good and very bad things would happen to both Pitch Black and himself.