I wonder if he means “the greatest” in terms of in-universe fame…?
Dunno if this is the case in Canon (then again Dave Filoni blatantly ignores any *non-motion* transmedia elements in Canon so meh), but in Legends he’s:
“Anakin Skywalker, the Hero with no Fear™, handsome, dashing, the face of the Republic’s army during the Clone War, the only Jedi who tried to resist the nefarious Order’s coup and was treacherously murdered for it”.
And I seem to remember that, in Canon, he’s like the Jedi Temple’s superstar anyway, every Jedi recognizes him on sight. I mean, that line from Baylon about “Anakin speaking highly of Ahsoka” must have some meaning beyond artificial personal stakes.
So from a fame and a “power level” standpoint… sure.
He’s the greatest.
I’m giving Filoni the benefit of the doubt.
While I’ve talked about why Filoni’s entire headcanon about the Jedi doesn’t track with what George Lucas’ intended narrative, I think it’s worth acknowledging that Filoni’s bias comes from part of his duties while directing The Clone Wars was.
One of the goals of TCW was humanizing Anakin, expanding upon his character make him go from “a character whose only purposes is to embody the themes presented in three movies based on the matinee serial format” to a relatable person, a good man, the hero Ben mentions to Luke in A New Hope.
I think it’s normal that he’ll see Anakin in a more positive light.
Also (and full disclosure this is just me theorizing I am no authority on any of this so if turns out I’m wrong just come right out and say so)…
I’m pretty sure that Filoni, Lesley Headland and most of the recent Star Wars authors are all Gen X, raised by baby boomers forced to conform to society, obey authority and have proper decorum (boys don’t cry!) all of which they strove to rebel against. Add to that the corruption they witnessed growing up and coming out of high school, and you see a kind of jadedness emerge. “The rules aren’t as black and white, the world is grey.”
So while most of them and the boomers despised the Prequels upon release, a few of them projected a more individualistic headcanon onto those movies that fit with where their head was, at the time.
As such: Anakin isn’t interpreted by them as a cautionary tale about what happens when you’re greedy. He’s a misunderstood rebel, a non-conformist who has his flaws but is ultimately good at heart. Which isn’t entirely inaccurate, but it is very clearly an embellishment of a character who will one day become a space nazi.
The fact is… the Prequels were made by a boomer. One with very liberal values and who was himself a rebel, but a boomer all the same. The whole point of his story is…
“we all must come together and fight as one, if push comes to shove; we must all be compassionate and selfless if we are to survive; don’t be greedy, let people go when it’s their time to leave”.
And then he makes the Jedi say that, making them beacons of truth and good and compassion in his fairy tale, now aimed at Gen Z kids.
Gen X-ers hear/read that and project all the boomer BS they had been told onto the Jedi…
“oh, so the Jedi are saying you shouldn’t love yourself, you shouldn’t be yourself, you should give up on what makes you an individual to fit in, you shouldn’t feel any emotions”
Because nobody is that good, realistically, right?
This happened in other mediums. The one that comes to mind on the spot is the relationship between Mufasa and Scar.
In The Lion King, Mufasa is strong and noble, Scar is weak and conniving. Simple enough. Around that same time, in A Tale of Two Brothers, young Mufasa is shown to be pretty nice with Taka (Scar), who is framed as a spoiled brat to begin with.
Skip to the 2019 remake, and it’s hinted Mufasa gave Scar his wound, and in The Lion Guard they explain that Scar got his nickname from Mufasa mocking him for a misadventure.
He went from being a noble king to a bully who had it coming, Scar is an underdog who got picked on. Because again: nobody is that pure, right? Fairytales be-damned.
Nothing is black and white, it’s all grey.
So yeah, long story short I do think that Filoni being part of the generation that wasn’t the target demographic but was old enough to retcon the crap out of the Prequels also plays a role into his view of Anakin.