It is because of the Rule of Two.

Imagine these two individuals:

Beng the only Jedi. If the Jedi adopted the Sith system, Yoda would be master, Windu would be apprentice, and all the others would be nothing. Qui-Gon falls into this category of “nothing”.

Sith and Jedi titles are incomparable. There are hundreds of Jedi masters. All it takes to become a “master” for a Jedi is to complete training and then train someone else.

To be the “master” of Sith? You’d have to be pretty much the strongest dark sider. The strongest. Not among thousands. And to be an “apprentice” you’d be the best that the master can find.

Plus, for Jedi, “apprentice” equates to “unfinished training”. While for Sith, “apprentice” just means you’re not the master yet — the Sith apprentice is usually fully trained and highly dangerous.

Qui-Gon was good, but nowhere near Yoda or Windu level. Maul’s status was the Sith equivalent of Windu’s status, and he overpowered Qui-Gon.

I’m assuming you mean this by the two Jedi.

And this by the one.

To put it bluntly, Maul was overconfident.

As far as he was concerned, his opponent was already dead. And, against most people, that would be true. Disarmed, barely hanging on to a ledge while stuck in a hole.

Unfortunately for Maul, Obi-Wan was resilient. Not only that, but he took one of his master’s last lessons to heart.

Keep your concentration here and now, where it belongs.

Obi-Wan, mind in the present, was able to think on his feet and find a way out of a seemingly unwinnable situation, by taking his fallen Master’s lightsaber and using that to defeat Maul.

Even so, Maul may have been able to avert this, had he had heard and heeded that same advice. His mind in the future (the dead Padawan, his master’s approval, eventually revenge on all the Jedi) he was unprepared for Obi-Wan’s renewed, and final, attack.

Darth Maul was an absolute savage with his sabers, however Darth Sidious was just on another level really.

Darth Maul mastered two forms of lightsaber combat. Those being form 6 Niman which was a combination of the previous five forms and form 7 Juyo which was a common form used by Sith as it would often enrage the user.

Sidious on the other hand mastered all 7 forms of lightsaber combat. The only other force user that had mastered all 7 forms other than Sidious was Yoda. Sidious could use whatever form he wanted depending on the situation really, or he could use a hybridised form by incorporating moves from each into one.

However this is not to say that the gap between both Sith’s saber prowess was massive.

Maul was an amazing duelist and managed to hold his own against Sidious the moment his brother Savage got killed and he got engaged.

Proving that he wasn't too far off from Sidious's level. But he just wasn't there yet at his master's level.

See the thing about Sidious is that, he was basically a master of everything while most others in the galaxy weren't at their peaks yet. Maul was reaching his peak, Sidious however already was there!

This question seems to me to be backwards. You’re looking at Darth Sidious beating Darth Maul in a duel, and concluding that he doesn’t have dueling prowess.

The whole point of this scene is that Sidious is much better with a lightsaber than Maul anticipated. It plays on Maul’s preconceptions, and the audience’s, to further Maul’s character arc.

So let’s back up and discuss that for a moment. One of the things that Star Wars is unequivocal about is that the Sith are wrong. The Sith and the Jedi aren’t two sides of the same coin. The Jedi have their problems—many and varied problems—but they don’t hold a candle to how problematic the Sith are.

You’ve got to remember that the Sith are not just “people who use the Dark Side.” In Lucas’ Methodist-Buddhist, Campbellian worldview, there is room in a balanced world for both the Light and Dark sides of the Force. But the Sith … no. Those guys are a morally bankrupt cancer. Lucas has compared Palpatine to Satan. The Satanic elements of Maul’s character design should be obvious.

It’s … not subtle.

And, in the best Satanic tradition (or the best tradition of traditional Christian views of Satan), the Sith can present themselves well … but it’s all smoke and mirrors. There’s no moral substance underneath. Knights of the Old Republic is my favorite (and, in my opinion, underappreciated) example of this. For a while, the Sith and the Sith Code seem rather attractive, especially to the unattachment-on-steroids Jedi. It can sound like the Sith are actually all about self-actualization and empowerment.

And then you actually get to the Sith Academy on Korriban and find out they’re a bunch of emotionally stunted backstabbing victims of an abusive cult whose actual religion is perpetuating the cycle of abuse. They’re not edgy. They’re not misunderstood. The entire Sith religion is a monstrous lie.

Darth Maul exemplifies this. His hatred and rage and does not allow him to triumph on Naboo. Following his defeat and dismemberment, he turns to Sidious’ Sith teachings to keep him alive, to regain his power base … and all for what? So he can be humiliated by his master and then die at the hands of the man he hates, who pities him?

What Maul’s confrontation with Sidious shows is that all his assiduous attempts to follow the way of the Sith have given him nothing. Sidious—the great devil himself—outclasses Maul in every conceivable way. He is pathetic, a miserable echo of the man he idolizes, so pitiful that even his attempts at evil and cruelty are merely a child’s pretend. Compare Maul’s reaction to Savage’s death to Sidious’ heartless, pitiless laugh. Maul’s attempts to gain power through the way of the Sith have ultimately availed him nothing. It never would have. The way of the Sith is a lie.

Maul himself never learns this. He spends the rest of his life pathetically consumed with rage, nothing more than a toddler with a lightsaber throwing a tantrum and thinking it makes him powerful. But we do, and perhaps even come to pity the great fool who thought himself a devil.

But in order for the audience to understand this, it is important that Sidious outclass Maul in every conceivable way.

Sidious’ appearance makes it clear enough that he is some kind of dark wizard in SPAAACE!!!!

Whereas Maul, of course, is clearly remarkable primarily for his prowess with a lightsaber.

All of this has been clear from the very first time we saw the characters. Which is why it’s important that Sidious destroy Maul with a lightsaber. If he had beaten him with his dark wizardry, the lesson would not be clear. But when Sidious not only goes blade to blade with Maul and his brother but beats them … that’s a pwning that only someone as blind as Darth Maul could overlook.

All his rage. All his devotion to his Sith training. All his pontificating about power and the Dark Side and his master’s teachings … and he’s still just a pathetic imitation of Sidious. He isn’t even as good as Darth Sidious with a lightsaber!

You got lied to, Maul. This was never a pathway to true power.

We’ve seen this before, of course, when Sidious pulls out his lightsaber at the end of Episode III. But Sidious’ lightsaber fight against Mace Windu et al. was so unconvincingly filmed that it occasioned all sorts of after-the-fact explanations as to how Sidious won. Since The Clone Wars was not constrained by Ian McDiarmid’s lack of athleticism and stunt training, nor the inexplicable failure to allot adequate production time to film the scene, it could show Sidious simply being a fabulous duelist.

Because it’s not enough that Maul lose. The whole point of the scene is that Maul be outclassed in every conceivable way.

Ahsoka Tano as we encounter her on Mandalore is not the same 14-year-old girl that met all those years ago.

She has trained religiously for years with the greatest Jedi teachers and Anakin Skywalker in skills further honed by years of frontline combat against some of the toughest foes of that era.

I think it is important to remember that Maul, for all his menacing facade, is a haunted, broken man who spent many of the intervening years between his duel with Obi Wan and the end of the Clone War wracked with madness, failure, fear and loss. Even at this early time, he is a terrorized shell of the man he once was with little left to sustain him, but pure instinct for survival.

A cornered beast is violent and unpredictable, but a hone weapon is more dangerous.

Maul is also not invested in this fight. He is desperate for help. Failing that, he is desperate to escape. Killing Ahsoka Tano is only a priority in so much as she is hampering his attempt flee and hide.

Despite Maul's skill and determination, there were several reasons why he ultimately failed to defeat Sidious.

Firstly, Sidious was an incredibly powerful and skilled Sith Lord, with many years of experience and training, and he himself raised and trained Maul since childhood, fashioned him into his loyal servant, knowing all about his former apprentice's personality, strengths, and weaknesses, not to mention his overall fighting style, modeled after his own.

Ultimately, this allowed Darth Sidious to easily block and counter Maul's attacks, while keeping Savage Opress at bay.

Secondly, Sidious was able to use his superior Force abilities to overpower Maul, throwing him around the room and ultimately disarming him, and although Maul possessed a raw connection to the Force, perhaps even rivaling if not surpassing Sidious's, the old man's abilities eclipsed his powers due to the greater knowledge and experience at his disposal.

Lastly, Maul was also emotionally compromised during the duel. He was consumed with his hatred for Sidious and his desire for revenge, which clouded his judgment and left him vulnerable to Sidious' attacks. Maul wasn't ready to face his former master yet and was clearly caught off guard when the old man came himself to challenge him on Mandalore, not to mention the death of his brother during the battle.

In the end, Sidious proved too powerful for Maul to defeat at this point in time. However, Maul's fight against Sidious served as a testament to his strength and skill as a warrior, and his willingness to stand up against even the most powerful opponents.

But Darth Sidious was simply a superior and most experienced duelist and master of the dark side, combined with his prior knowledge of Maul's abilities and skills. Darth Maul's overall abilities were simply not quite enough to defeat the arguably most powerful Sith Lord in the entire history of the Sith Order, and his former master.

I really like Maul, and I will admit his feats are impressive.

But I gotta hand it to Sidious…Maul may be powerful, but he’s nowhere near as powerful as Darth Sidious.

Okay, Maul may be amazing and extremely skilled with a lightsaber, but Sidious is, for a lack of better words, the best.

Sidious is often regarded as the most powerful Sith (in canon at least) ever, and the smartest too. His devotion in the Dark Side helped him gain power, and his skills helped him gain fear in the people.

(This art lowkey scared me)

As far as Sith go, Sidious is the most, and if not, one of the most, powerful.

And his lightsaber skills aren’t to be slept on, either.

It’s kinda like the Jedi. Take Aayla Secura, for example. She’s extremely powerful, like all Jedi are, and had impressive abilities. But as far as skills go, she’s nowhere near someone like Mace, or Yoda, or even Anakin.

It’s the same with Maul and Sidious; Maul may be good, but Sidious just was, again for a lack of better words, better.

Hope this helped :)

May the Force be with you.

Weak? If he was weak, he wouldn't have been able to kill one of the strongest Jedi in the temple.

Evenly match the greatest duelist the Jedi have to offer, while also fighting an extremely powerful Master along with him.

Make Kenobi look like a joke.

Shortly stalemate a Sith Lord who's equal to Yoda in almost every way.

Easily beat Savage, someone who's beat both Kenobi and Anakin at once.

Bring down a Star Destroyer by destroying the inside.

And he could've easily killed Grievous if he wanted to, someone who can contend with Obi.

Maul is by no means, weak.

Whether it’s canon or legends Vader vs Maul, Vader wins this pretty easily.

Maul does have impressive feats and was renowned as a Sith, but he pales in comparison to Darth Vader, the Chosen One. Maul had been bested by Obi-Wan fairly easily. Twice.

Ahsoka Tano was also able to best the Sith assassin and eventually managed to beat him.

_

Vader, on the other hand, has some impressive feats: one of them was being able to take on an entire army.

Vader was also able at one point to take the full power of flamethrowers without flinching

_

At the end of the day, perhaps the greatest piece of evidence was Vader’s ability to kill Maul in one comic:

_

At the end of the day, when it comes down to it, Vader is just more in tuned with the force and a superior duelist to Maul.

Judging from his reaction to Vaders incoming approach, in Rebels, I'd say that Maul held a healthy degree of fear towards Darth Vader. Before Maul and Ezra Bridger met up on Malachor Darth Vader had already dispatched his Inquisitors to the ancient Sith Temple, built by Darth Tanis nearly 4000 years previously. Vader was more than aware of Maul thanks to Palpatine, and as for the Dathomirian he knew of Vaders tremendous powers. He knew that his former master had taken Skywalker as the apprentice that he should have become, and he knew that Vader had not only been trained by Sidious..but commanded the entire might of the Galactic Empire.

Vader had been doing the bidding of Darth Sidious for over a decade and a half at this point, and would stop at nothing to not only eradicate the last remnants of the Jedi,…but annihilate any possible threat to his power. That included Maul, being Vaders predecessor, and a living violation of ‘The Rule of Two’. In Vaders eyes Maul should not exist…and Maul knew it.

During the last hours of the Galactic Republic Maul knew that Darth Sidious would be taking on his new apprentice, and after the rise of the Galactic Empire Maul knew the extent of Vaders reach. He also knew that he could not survive in single combat against Vader, and that his rage was something to never provoke.

He feared him for various reasons, but he feared him most because the former Sith Lord knew of the Jedi prophecy of ‘The Chosen One’. He knew what that entailed, and even in his last moments alive he had to know if Skywalker really was the prophesied bringer of balance to the force. He didn't want to stand in Vaders way, because Vader was the one man alive who could achieve what he dreamed of most;..killing Palpatine and destroying the Sith Order.

Maul feared Vader because he knew if the prophecy was true there would absolutely be no stopping him; until Vader had finally stopped Sidious first. Kenobi relieved his doubts, and as Maul died he believed that the chosen one would avenge he and Kenobi both.

It’s mostly part of his personality, but the root of this comes from his upbringing.

For essentially his entire life, Maul’s master has been preparing and hyping him up for the time when they will take their revenge on the Jedi Order and rule the galaxy. That has to create quite a high opinion of oneself. He has been training physically and mentally for that moment for 20-odd years, dedicating his every fiber of being to ready himself for it. He is supremely confident in his abilities, and this confidence brims over into outright arrogance. He believes he is prepared for any meager challenge the Jedi can possibly throw his way, that he will be the instrument of their destruction and pave the way for the Dark Side’s final victory.

Maul was far from incompetent. Maul even excelled beyond just competent. He was highly proficient at most anything he was tasked to do or set his mind to do.

MOST IMPORTANTLY, as far as this one question goes, we have reference books from old and new canon that say quite the opposite of the what the questioner assumes. I will add screen captures of the pages from the books and comics at the end of this answer, but we know from these sources that Maul was, out of the entire history of the Sith Order, one of the most skilled, most dangerous, most efficiently trained, and most deadly Sith and/ or Sith apprentices. It is canon that Maul > Dooku, as well. If Maul was incompetent, then why did Sidious consider him a loss (also new canon) and not Dooku?

1. Sidious greatly valued Maul.
   
   During the time that he was Sidious’ apprentice, he showed extreme skill and capability and accomplished what his master tasked of him. He was what Sidious wanted of an apprentice, and when Sidious thought he died, he became physically sick. In another novel, Lockdown, when Plagueis told him that Maul had to die, Sidious became physically ill as well. In the novel Darth Plagueis, Plagueis makes a comment that the relationship between Sidious and Maul was “almost filial.” In another novel, Sidious says that Maul is the most valuable thing to him. I can’t remember the exact noun, but “most valuable” was used.
2. Sidious intended and trained Maul to replace him.
   
   It is stated repeatedly in Legends and in new canon that Maul was indeed intended to be Sidious’ replacement. This was before Sidious learned of Anakin’s existence, though. Maul would have to be exceedingly competent to be the intended replacement of the most powerful Sith ever in the entire history of the Sith Order. Someone like that…no, not “someone”, not just anyone. A Sith that powerful would never entertain incompetence of any type.
3. Maul completed many missions as an apprentice and accomplished his tasks.
   
   Legends has some great stories that details these missions.
4. Maul was cut down by Kenobi only because of gloating (canon and Legends).
   
   In Legends, there are several novels and reference books that detail this.
5. Maul accomplished a lot before being beaten by Sidious, the most powerful being in the galaxy.
   
   I am not sure where the idea comes from that he was incompetent. It took highly skilled and powerful beings to defeat him. He took control of the three most powerful crime syndicates in the galaxy after taking control of a group of some of the most capable warriors (Death Watch).
6. There are interviews with Dave Filoni and Sam Witwer, who, although an actor, helped create the character of Maul for The Clone Wars and for Rebels, and in the interviews, they say that Maul had been trained to help Sidious complete the Sith’s Grand Plan. Sidious did intend for Maul to be his right hand man in the same manner as we saw Dooku in The Clones. Maul commanded armies of men in The Clone Wars, as well as in Legends short story, “End Game”, he successfully lead droid troops in the invasion of Naboo and was addressed as “Commander.”

There is way too much to detail to fully reply to this incorrect assumption that Maul was incompetent. At least we have the following canon and Legends sources to correct it. There is more than what I’m adding below, but, again, it’s just too much. In no way was Maul incompetent.

New Canon:

New Canon:

Legends:

Legends:

New Canon:

Depends on your definition of evil I suppose. I would argue no he wasn’t truly evil.

Maul was stolen as a child by Sidious away from his mother Talzin and never experienced any love or affection in his life. He was stolen to become a Sith.

To become a powerful evil force user. Sidious was successful in turning Maul into Darth Maul.

What did he do so evil to begin his life? Nothing too bad but by the end of his life he’d committed some horrible atrocities.

Maul also hated the Jedi. He hated them and was filled with rage because he realized that as a child they never came for him.

Maul did not know if they found him unworthy or simply ignored him but their neglect fueled his rage counting the days until he could have his revenge.

He was impatient with his master's planning, resenting the pain and suffering he felt as he waited for his time to unleash himself on the galaxy that had hurt him so much.

Was Maul truly evil? He was fueled completely by hate and rage. Some of his acts resulted in great evil though.

He had killed the Duchess Satine, tried to kill Obi-Wan multiple times and killed numerous Mandalorians, slaughtered women and children , Crimson Dawn, other innocent and criminals etc.

He even tried to kill Kanan Jarrus and tried to corrupt Ezra Bridger. His sole motivation for most of his life was to torture and kill Obi Wan.

He was obsessed with Kenobi.

He even kept a creepy shrine to the Duchess Satine and Obi Wan.

Maul survived and lived so long on hate. There are many redemption stories for numerous number of villains ranging from Kylo Ren to Darth Vader.

When Maul was finally dying maybe for the first time in his life his rage left him as Obi-Wan cradled him.

Maul finally meets his end

Because Maul asked with his last breath if Luke was the chosen one.

When Obi-Wan answered in the affirmative, Maul looked at peace for the first time in his life and said, “Good he will avenge us.”

For a being that was born and bred in hate and violence to him that was the ultimate justice. For Maul that was a good thing.

Maybe at the last moment in his life Maul finally was not truly evil. Maybe he never was. Maybe he was just an angry bitter being filled with rage until the last moment of his life.

I hope that clears up any confusion!

I ❤️C2, questions, disagreements, curses and hexes!

-Jason

He has to abandon his preferred fighting style because he's covering Anakin, which means he has to keep pace with him, something that destroys Kenobi's entire form. Obi-Wan being a defensive fighter, isn't supposed to be rushing his opponent.

We've seen him do better against Dooku alone. He doesn't have to change his fighting style to match Skywalker’s energy.

Extremely powerful. Darth Maul has to be one of the most underrated fictional characters ever. Some people think he was only an assassin. Nothing more. That couldn't be further from the truth. He was implied to be holding off Sidious while Talzin regained her power.

He landed a kick on Sidious, while rage amped from Savage’s death.

Fought against both Aayla Secura, and Mace Windu. Two of the strongest Jedi of their time.

Easily beat an angry Kenobi. Although the Jedi was weakend.

Charged Grievous, making him submit.

Without effort, defeated Savage. Someone who used his physical power to beat Anakin and Obi-Wan.

He ranks above Dooku in dueling.

Ventress was getting overwhelmed by Maul's strikes.

He's fast enough to dodge a rocket.

Create four afterimages while blocking blaster fire.

Spin his saber fast enough to block rocks being thrown by the force.

Jumped over an attack from Sidious.

And casually block an attack from a Jedi Knight. Without even looking.

He took Palpatine’s lightning for who knows how long.

Took a grenade from point blank range.

Maul didn't talk, even after Dooku used force lightning to try and make him.

Threw Kenobi all the way down a tunnel. Collapsing it.

Pushed away several battle droids.

Force pushed Grievous through a concrete wall.

He even destroyed a Star Destroyer's hyperdrive.

There you have it, Darth Maul is extremely powerful, and extremely underrated.

Maul is the living embodiment of the aphorism “Pride goeth before the fall".

He is a perfectly exceptional duelist on some abstract, technical level. But his arrogance is without any bounds. Far beyond his rather modest station in the overall scheme of things. Believing his natural talent is peerless and will always carry him against any opponent.

Leading him to often fight unseriously and in a mocking way against enemies who are far more grim in their determination. Treating opponents mockingly is a fatal flaw against those whose conviction is deadly.

He’s not?

No, but seriously. Maul is one of the most overrated characters in the Star Wars universe. Maul isn’t quite as popular as Vader (who is one of the most popular fictional characters just about ever), MAYBE Maul isn’t as popular as Sidious (though he probably is, I haven’t seen the stats), but he is definitely more popular than Dooku.

Why, you ask?

I honestly have no idea.

Maul:

Looks cool

The majority of fans: “Such a masterful and interesting character.”

Dooku:

An ex-Jedi who joins the Sith in order to destroy the Sith Order from within, is seen as a villain by the Jedi and the Republic, and because he is betrayed by his master before he could betray him, is remembered as a villain

The majority of fans: “Boring placeholder.”

This isn’t even counting the Sith Lords from the EU, who lots of people have never heard of.

Basically, no, Maul is definitely as popular as the other Sith Lords.

Darth Maul performed very well against two Jedis and would have won if he had a tiny bit more practical mindset. But that is the core. Sith apprentices are meant to be immensely Forceful executioners and not tactical geniuses. Any sane Sith master would want to enslave the strongest available conscious creature in the galaxy that could easily be fooled with lies and manipulated through his/her/its emotions or ambitions. (Palpatine always TALKS about use of fear and anger, but never seen ACTING out of either. Neither Snoke. Being smug is another issue…) Darth Maul, Darth Tyranus and Darth Vader are variations for the same theme, just stronger and stronger versions. Remember Darth Vader’s battle entry over Scarif in the Rogue One? Spectacular as hell, but not exactly cunning…

“Evil” is a very broad concept.

Darth Maul was twisted since childhood by Darth Sidious, molded, corrupted and altered by the dark side.

Ultimately, he indeed became completely amoral, profoundly wicked, he wasn't redeemable, he's one of the worst out there.

Maybe, in another life, he could have been different, if he wasn’t abducted from Talzin by the Sith, taking away from his kinsmen and heritage on Dathomir, from his mother and blood brother.

Or perhaps, if he was found by the Jedi as a child, then Maul might have been a fantastic, or at least, decent person.

But as a Sith Lord? Darth Maul was a truly cruel and heartless warrior, willing to go to great lengths to achieve his vengeance, and gain more power and strength, and came to embody the obsessive and frenzied aspects of Sith revenge.

Maul was deeply indoctrinated in Sith dogma and a true Sith can never find fulfillment because they perpetually look for more power.

Well maul is still life long martial warrior with decades of combative experience and has retained most of his skill through mussle memory.

He has been confirmed to being stronger than rebels ahsoka who in turn can challenge prime vader as a fighter.

Vader level fighter(although inferior By slim degree) like that so it comes as no suprise he can clown inguisitors.

I don’t think Palpatine was racist at all.

He doesn’t seem like the type of evil who would go that low.

Remember that the Clone Wars was a thing that Palpatine concocted so that he could reap and exploit its results.

One such result was the galaxy at large developing hatred for the aliens and droids that enslaved them before the Republic/Empire rescued them from that fate.

What else to gain the loyalty of racist citizens other than to enact racist laws that pander to those people, laws that give them power, and by extension you?

Palpatine wasn’t racist.

In fact he got along with figures like Thrawn and Maul quite nicely (as you pointed out).

However, Palpatine was a creature that fed off power, and did whatever it took to get it, whether it be kidnapping children, exploiting people’s fears for their loved ones, or pandering to racists.

Several reasons. The first being that Obi-Wan was dam pissed off and just itching to get at Maul as you could clearly see. He was WAITING for that energy barrier to go down so he could get right at Maul.

Of course that first volley which was excellent didn't land anything at that time and the fight was about even until Maul force pushed Obi-Wan off the ledge.

He never expected Obi-Wan would be strong enough for force pull himself up from the ledge and call Qui-Gons lightsaber to him and cut him in half. Maul was over confident where as Obi-Wan was learning to trust in the living Force more and more from his master. Also

It's the same reason why Obi-Wan and Yoda didn't go after together but each took on one of the sith, Obi-Wan going after Vader and Yoda after Sidious. It's because Yoda KNEW that the sith were training for decades to take on the entire Jedi order and that their training likely revolved around being experts at taking on multiple Jedi at once.

This is why Sidious was able to take out three of the best Jedi Masters in matter of seconds, but when he was one on one against someone as good as Mace, he was having a lot of trouble and eventually lost. Yoda probably realized this from Obi-Wan's report in his dual against Darth maul and how he was taking them both on but eventually once it was just Obi-Wan and Maul, Obi-Wan was starting to make headway, even cutting his weapon in half and getting some strikes in on Maul before maul force pushed him over the ledge.

This is why in the novel of Revenge of the Sith, Obi-Wan said to Yoda that Sidious took out 4 of the best Masters in the order, even you and I together won't stand a chance (which I don't think is correct). Yoda replied that together they won't, but one on one they might. That's why Yoda went to confront Sidious and sent Obi-Wan to seek out and destroy Anakin.

Of course the strategy worked and even though Yoda wasn't able to take out Palpatine, he did hold his own and Obi-Wan was successful against Anakin.

In real Martial arts, generally if you can take on several people at once FOR REAL, you'll have an easier time with just one person but it Can depend on how you were trained because taking on several people at once with weapons can be quite different from a one on one confrontation and if you practice more against multiple opponents than a single person you could be defeated by a skilled opponent that it training more in single person combat.

The Jedi had NO NEED to practice taking on several Sith at once because they were believed to be extinct. But the sith KNEW that they would be possibly facing several Jedi at once and trained more for that type of combat, but the Jedi were better at one on one because that's how they mostly trained among master and student.

Yoda was Well versed in taking on multiple opponents at once and even did a demo without any weapons and he asked three of the best Jedi Masters to attack him unarmed. With sometimes almost imperceptible movements, Yoda stepped, shifted, jumped, dodged, weaved, slipped, bobbed, rolled, flipped and avoided every single saber strikes from the Masters for a good 30 seconds. Even the top Masters who thought they knew how skillful Yoda really was were blown away by his empty hand vs. Weapon skills.

So because Yoda was so skilled in multi and single opponent Combat and everything in between, he knew that the best course of action would be to take them one on one.

So this is likely another of the reasons that Obi-Wan' defeated Maul the first time other than Obi-Wan's great focus and determination. When he defeated Maul he was infuriated over Qui-Gons death. When he defeated Vader, even Sidious was surprised and impressed and said that if the entire Jedi order had the kind of focus and determination that Obi-Wan showed he never would have been able to get a junior senators seat on the council let alone be elected chancellor.

His own. During his peak, in the Clone Wars. He made his own faction. And while it wasn't nearly as big as the rest. It was big enough to cause a few problems. Being the King of Mandalor meant the strongest warriors in the galaxy all stood behind him.

He wasn't under the Sith.

Or beside the Jedi.