Mace Windu may discipline him very well, but I'm not sure if he's gonna be more sympathetic to him than he is.

Not immediately for sure. But after seeing the darkness within Anakin, I feel like he’d see a bit of himself & come to better relate to him over time.

I don’t think they’d be playful w/ each other like Anakin was w/ Obi-Wan, but I do think the experience would soften Windu towards him just a bit & they’d both develop a deep respect for one another.

I was with you until you said Mace Windu would be a better teacher for Anakin than Obi-Wan. Apart from potentially teaching him Vaapad, I feel like Mace would do everything that Obi-Wan did wrong except times 10. Obi-Wan’s main friction with Anakin was not understanding and properly empathizing with his feelings and talking them through with him, he just told him to ignore his feelings and follow the Jedi code even though doing so didn’t make Anakin stop breaking the Jedi code, it only made Anakin feel more alienated towards his master. Obi-Wan’s intentions were good and he did his best, but putting a rigid and by-the-book master with an impulsive and rebellious padawan wasn’t exactly the definition of a good match.

I doubt Mace Windu would do anything different from Obi-Wan in regards to getting Anakin to follow the Jedi code, he’ll definitely be more firm but Anakin is just as stubborn which could create even more friction than with Obi-Wan, and at the end of the day I don’t think firmness was what Anakin needed to not turn to the dark side, what he needed was a master who understood him and judging by how he wasn’t a fan of Mace and already had a connection to Obi-Wan, I think overall Obi-Wan was still the better choice as a master, albeit not the perfect choice.

I don’t think Obi-Wan experience or lack thereof really contributed to his slightly complicated relationship with Anakin, imo it was more of their core personalities being opposite and them having different priorities. For example, Anakin was made a Jedi Knight and master to a padawan at 19, which is 6 years younger than when Obi-Wan was Knighted, and yet he and Ahsoka meshed really well, rarely ever had an argument or disagreement, and helped each other grow into better people- and it was because they were both so similar in personality and temperament that Ahsoka grew to be even more similar to her master over the years, unlike with Anakin and Obi-Wan whose paths seemed to grow apart over time (by this I mean their priorities became more and more different, though their relationship obviously still stayed just as close as before). Anakin was super inexperienced at that point too, unlike Obi-Wan he wasn’t even the one who offered to train Ahsoka, the responsibility was just thrust upon him out of nowhere- plus he and Ahsoka had even more of a sibling relationship (instead of a student-mentor relationship) than Anakin and Obi-Wan- and yet I think he succeeded more as a master than Obi-Wan did.

All this isn’t to rag on Obi-Wan btw, he’s awesome and it wasn’t his fault he was paired with a mismatched padawan, but it does show that sometimes experience and authority doesn’t have much to do with being a good master, it’s having a good mutual understanding with your padawan.

What do you think? Would Windu have been the best choice or would another have done it better?

In a perfect world Qui-Gon would have been the best teacher for Anakin imo, he was wise, patient and moralistic yet also flexible and wasn’t as by-the-book as Obi-Wan and Windu, but if canon cannot be changed and we can only pick from one of the Jedi who are alive, then I honestly don’t know.

If Qui-Gon didn’t die i would go with him to train Anakin

Anakin might have had a better fate if Qui-Gon was there for him

In my opinion, Mace Windu wouldn’t have been a good pick for Anakin

Qui Gon most definitely, he probably was the person Anakin was the closest to.

I think people don’t give enough credit to Mace. He may come across as more reserved and distanced than other Jedi but that doesn’t make him automatically less compassionate. On the contrary, he is shown to be quite compassionate and to care about others in TCW. He’s certainly more than just a dogmatic guy or a grump, lol.

I personally think you make great points about Mace as a potential master to Anakin. Especially considering that there was a time where he had faith in Anakin, I strongly agree that he would be a good choice in this matter, mainly because of the points you raised.

Another promising alternative would be Qui-Gon, in my opinion. Anakin would likely feel safe with him and given how patient, understanding, compassionate, and unorthodox Qui-Gon himself is, he would probably make a good guide to someone who has quite a lot of insecurities and who struggles with adapting. On the other hand, his own unorthodox ways could make it also more difficult for Anakin to integrate into the Order. But he would remain my second choice in this matter

Qui-Gon for sure because he was the only who believed in Anakin and he was willing to train Anakin where Obi-Wan wasn’t ready for the training

Plus I think Qui-Gon would have been able to make sure that Anakin’s chosen one path would have stayed him on the path of good and not turn to the Dark Side

For the record, I wholehearted agree Qui-Gon would have been best suited. I suppose I should have specified who was alive & capable of teaching him in the aftermath of Phantom Menace.

Although I may disagree with your conclusion, I appreciate the effort it took you to write up your detailed arguments in favor of your selected candidate! I can respect the arguments regardless.

Thank you!!!

In my case, I would have selected Grand Master Yoda, but that is only if Obi Wan was not available to begin with.

I think the original choice, Obi Wan, was the right choice. If the motivation was to prevent Anakin from becoming Vader, I am not confident any master would have prevented that fall, given Anakin's inherent demeanor, and Palpatine's intense grooming to turn him dark.