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Highlander 2 really really needed to listen to the tag line. "There can be only one" wasn't just cool sounding. It was a warning.

I'd say obi wan friendship was part of the issue. Anakin didn't need a friend he needed a father figure. Obi Wan was to young and inexperienced to provide that. Which is why sheev was able to undercut them. Because he did provide a father figure as opposed to a friend/brother.