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Well, according The Mandalorian executive producer Dave Filoni, the team did briefly consider bringing back Hayden Christensen for this flashback sequence.
“I discussed it with [showrunner Jon Favreau] briefly and I said, you know, there were some opportunities there. We always have to kind of look at every possibility,” Filoni told Insider during the PaleyFest LA TV festival. Ultimately, the team decided against an Anakin cameo for a very specific reason.
“At the end of the day though, a character like Anakin, one of George’s characters, we have to be very careful how we utilize those characters. It’s very special when we do. So, I think we quickly moved away from that,” Filoni explained. They also didn’t want the surprise return of Anakin Skywalker to eclipse what was a very important moment for Grogu: “We wanted Grogu to have his own story and tell it a slightly different way.”
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Like many fans forming their own headcanon, Filoni does find it very interesting that Anakin and Grogu were both at the Jedi Temple at the same time, and may have crossed paths at some point during Anakin’s early training.
“It’s interesting to think that they were that close to each other,” Filoni said. “And interesting to think that even when Anakin was a little boy, that he was there at the temple at the same time as Grogu. So there’s all kinds of weird things to melt your brain and wrap your head around, but, in a fun way.”
Does this mean there could be a way to show Anakin meeting Grogu at some point before Order 66, perhaps even before Anakin left Coruscant to fight in the Clone Wars? We’ve already seen Lucasfilm de-age Christensen to play an Attack of the Clones-era Anakin in Obi-Wan Kenobi, so it’s not an impossibility. Since Grogu is already 50 years old during The Mandalorian, and Anakin joined the Jedi Order about 40 years before the start of the show, that’s plenty of time for the two characters to have run into each other at some point on the Star Wars timeline. Maybe they met right after The Phantom Menace?
