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First of all, let me clarify this: when I first read Into The Wild, I actually liked Raggedstar- obviously not his choices (*cough cough*, taking his medicine cat as a mate). He was described as brave, calm and wise, and so do the books beyond that. Yellowfang's Secret just changed my opinion on this leader forever and made he realize what a horrible leader he is.
He is selfish, unseeing and he barely cares about his clan's future.
Spoilers for Yellowfang's Secret below.

Breaking the code

This is something that I disliked about him from the start. He's the leader of his clan, he should be enforcing the rules and making sure every cat is loyal to him and only to him. Not only that he broke the Warrior Code himself, but he encouraged Yellowfang (who literally has no self-control, by the way) to do the same. He was particularly on his knees begging Yellowfang to break the Warrior Code and be with him despite her being a medicine cat and when clearly, she was trying hard to be a loyal member of the clan.
What sort of leader does that? Even though he was only deputy at the time, he should have known better- The warrior code is there for a reason. Medicine cats should concentrate on their duties fully, and having a mate would distract them. One cannot enforce rules they do not comply to themselves. Without rules, no society can hold, and it should be a leader's duty to enforce them- breaking them is totally unacceptable, especially when he is encouraging others to do so as well.

Brokenstar

I literally was laughing as I read through how Raggedstar dealt with his son, Brokenstar. Raggedstar has no real judgement and his incredible bias shown towards his son is laughable. His arrogance just makes me gawk at the pages with absolute wonder of how this cat became deputy in the first place.
In the gathering, Brokenstar attacks a couple of apprentices, and Cedarstar rebukes the apprentice in front of the whole gathering. Raggedstar then says something that made me suppress a laugh of scorn,
"Brokenpaw was only defending ShadowClan's honour! [...] Loyalty and courage mean more than rules."
--- Page 370
Yeah, sure. Only defending ShadowClan's honor.
Defended ShadowClan's honor by breaking the truce and accusing cats based on his mere assumptions.
If you ask me, Raggedstar is nearly blinded by the fact that Brokenstar is his son and in front of him, he can see nothing. Everything his son does is right, even breaking a long held truce is nothing. Then he says rules mean little, which is untrue. No rules, no society. A society would collapse without regulations. If everybody can do what they want, what's the point? Raggedstar has no proof that his son attacked the WindClan cats out of loyalty, anyway.
That was just to show how much bias he shows towards Brokenstar, upcoming points show worse.
He later makes Brokenpaw into a warrior. Brokenpaw hasn't passed his final assessment, and Nightpelt reminds him about it. Raggedstar tells Nightpelt that he knows a cat is ready when he sees it. (382)
Raggedstar is just trying to push up his son as high as possible, almost blindly. Brokentail was clearly not ready, his over readiness to fight and his ignorance of the rules do not make him qualify for a warrior position, in my opinion. Raggedstar just makes his son a warrior, who obvious did not receive enough training. A warrior that isn't ready could endanger the clan- start unnecessary fights, etc. Raggedstar just blindly pushes his son to power without considering his clan's welfare.
Also pointing out that he had done this right after he received his nine lives, which means he had looked forwards to it for a long while.
Later, Brokentail brings back prey with some scent on it, and he wants the clan to attack. Raggedstar, agrees, and Yellowfang cautions Raggedstar that Brokenstar might be lying, but Raggedstar says that no son of his would lie, and tells Yellowfang to get lost.(408)
Yellowfang is his medicine cat, he should take advice from her, but he doesn't even consider her concerns worthy and just tells her to "get out of his way". Um. That is ridiculous. Also, who knows if his son "wouldn't lie"? Ragged star's blindness just makes me roll my eyes. A skirmish like this could cause serious injuries and even worse off, death. Rggaedstar barely considers anything and even when his medicine cat raises her concerns, he just shrugs them off. Unacceptable. His blind faith in his apparently perfect son later leads to his deputy's death, where he then makes Brokentail the deputy.
This is utter bull.
A skirmish just caused by his son kills the deputy, and now he's making him deputy? Wow, just wow. Yellowfang then cautions him to not replace CLoudpelt with Brokentail, but Raggedstar tells her to not ever question him again.(415) Raggedstar's ignorance of his clanmate's concerns and his blind determination to push Brokentail to the highest spot he can manage later nearly destroys his clan.
Not only that he is utterly blind to Brokentail's treacherous actions, but he barely cares for his clan anyway.

Foxheart

Foxheart... Was not a good choice for a deputy. But Raggedstar makes her one anyway. What really irked me was the reason why he made her deputy.
To make Yellowfang jealous.
This proves that he doesn't really care about his clan's welfare and only cares about his personal business. He didn't chose Foxheart because he thought she was a good cat, he did it to enhance one of his own personal "quarrels", which is pretty ridiculous. He doesn't even pause to think if Foxheart is the best cat to succeed him, all he thinks about is to try and infuriate his former mate, who clearly is only trying to be a loyal cat to the clan. Not to mention that his former mate is the medicine cat, whom he needs by his side for support. A soured relationship between leader and medicine cat could endanger the clan by far. Here Raggedstar not only endangers his clan, but he also promotes quarrel and unrest within his own community.

TL;DR

Raggedstar was a bad leader. Many problems ShadowClan faced later on can be traced back to his poor handling of his clan. Shame that this book ruined a supposedly good character.

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