The Mandalorian Season 4 Might Deliver a Major Crossover
The Mandalorian allowed the Star Wars franchise to recover from the blow, dealt by the sequel trilogy, and paved the way for creation of a string of live-action Star Wars TV series.
With most of these series set in the same timeframe, crossovers are to be expected. Boba Fett and Ahsoka appeared on The Mandalorian even before getting their own respective TV series, and are quite likely to appear again.
Another series likely to have a crossover with The Mandalorian in the future is Skeleton Crew, starring Jude Law. Star Wars creatives Jon Favreau and Dave Filoni mentioned this possibility in an interview. Favreau noted that when he'll be writing The Mandalorian's fourth season "all three new characters" will be available for him to use. As he explained (via):
"And now, I get to write the next season of The Mandalorian with all these new characters, and new locations, and new creatures, so it just keeps adding more and more, and so, where there's this cohesive group of stories that are being told thanks to all these filmmakers that are contributing. "
Dave Filoni, the writer and director of Ahsoka (as well as of several CG cartoon series) also clearly implied more incoming crossovers:
"You know, we have the greatest toy box in the world in Star Wars and so many great characters…"
However, he also mentioned that playing with those toys is not without its difficulties:
"I think the challenge is actually not when you start, it's where we are now, so many seasons in with Mando. So we don't just have Star Wars history and lore that came before us, we have our own that have been built upon, say just the Mandalorians, and the culture of wearing helmets, and not helmets, and how do those things intersect, which has become a big story point. "
Well, this does not sound entirely earnest, given Filoni's recent record of treating lore written by other people, but he raises a fair point about difficulties of writing a shared universe with complicated and constantly expanding lore. Whatever crossovers further seasons of the Mandalorian might have, writing them smoothly will take skill.