The Mandalorian secretly explains why Yoda and the Jedi High Council were skeptical of training Anakin Skywalker. Qui-Gon Jinn may have been convinced that the boy from Tatooine was the Chosen One in Star Wars: Episode I - The Phantom Menace but that didn't fast track his journey to becoming a Jedi - something that consistently frustrated him. On the surface, Anakin's contentious relationship with his superiors may have been what ultimately drove him to be easily manipulated by Emperor Palpatine who took advantage of his weakness and fed his ego.
When Anakin was freed on Tatooine and allowed to leave in the hopes of becoming a Jedi, he was made to believe that he's special - hence, it contributed to his expectations about his new path. Qui-Gon, with his more nurturing side, regularly appeased Anakin; unfortunately, when Qui-Gon died, Anakin was teamed up with a lesser-experienced Obi-Wan Kenobi who's essentially only carrying on his dead master's mission. The Jedi High Council was already opposed to training Anakin despite being the supposed Chosen One - something that would burden the young Padawan moving forward as it made him feel insecure and unappreciated by his superiors.
In hindsight, more actively training Anakin may have prevented his fall to the dark side. But while it appears as if this was the Jedi High Council's fault, The Mandalorian offers a better explanation for their decision through Ahsoka, who refused to train Grogu. Despite her official status, Anakin's former Padawan could still help Grogu hone his Force skills, but she turned it down, explaining that there is much fear in the Child, making him more vulnerable to the dark side. Instead, leaving Grogu untrained longer would result in the eventual disappearance of his Force capabilities. This would be safer than teaching him to control his power and risk the possibility that he would use it for nefarious reasons if he fell to the dark side just like Anakin did. Jedi Master Yoda had the same nagging feeling about Anakin when Obi-Wan asked for his permission to make him is Padawan in The Phantom Menace. He might have immediately recognized Anakin's attachment issues; training the young Skywalker would be a bad idea: "grave danger I feel in his training," the legendary Jedi shared.
While The Phantom Menace didn't further explain the reason why Yoda was against training Anakin, Ahsoka's refusal to take in Grogu in The Mandalorian justifies Yoda's original stance, which was initially perceived wrong. What's curious to know is whether or not leaving Anakin untrained would've actually resulted in all his Force powers fully fading considering his high midichlorian count. Anakin seemed oblivious to his capabilities when Qui-Gon and Obi-Wan first met him on Tatooine. If the Jedi left him on the desert planet unaware of his potential, does that mean that he would've continued to live not knowing how powerful he was with the Force, or would he have accidentally discovered it anyway?
Both Rey and Luke Skywalker tapped into their abilities much later than Anakin did, and yet both turned out to be capable Jedi. Grogu, who has gone years without guidance, also remains relatively powerful. So if Anakin is stronger with the Force than them, it might have taken longer for him to lose his powers, if at all. Given the lessons the Jedi learned from Anakin's fall, it's curious what approach Luke Skywalker will take with regard to training Grogu. Unlike Ahsoka, he took on Grogu as part of his efforts to rebuild the Jedi Order in The Mandalorian season 2 finale. Based on what's known in Star Wars canon, this new endeavor from Luke would also fail spectacularly following Ben Solo's turn, but one thing that hasn't been revealed is what happened to the Child.
