Greatest failure?

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Sheev
What character would you say has failed the hardest overall?

xPRIMEx
Maul is the first that comes to mind

Galan007
Yoda.

Lord Stark
Anakin Skywalker.

Tzeentch
Palpatine, followed by Anakin. Palpatine literally snatched defeat from the jaws of victory by just not being able to read the room.

ozz81
Anakin

Total Warrior
Anakin. Even more so in canon, where his final redemption and victory over Sid was apparently very short-lived.

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