I picked Philly because it allows him to stay in the East. But it all depends a few things. One, firing Lue. Two, severely upgrading our roster. Three, using the pick wisely.
I don't know if Gilbert would do any of those things without LeBron committing. If we're able to get Paul George for Love, trade for a real center using a mishmash of our pieces, find a coaching staff who can actually develop players and then draft a good player... That would be the only way I'd want him to stay. He's still the best player in the world, but he's done what he promised he'd do for Cleveland, and I'm happy for him to go out there and chase his legacy. Unfortunately, losing to Indiana would basically fuck up any chances of him catching Jordan, but so would losing in the East at all this season (which I can't see him avoiding unless at least 5 other players show up).