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One could argue having an unblemished Super Bowl record puts Montana ahead. His postseason stats are also better than Brady's by a fair margin. Just playing devil's advocate here.
Is winning the conference championship and losing a SB worse than losing a conference championship and not even making it to the SB?
I think not.
I would also point out that Brady has a higher winning % in the playoffs.
Montana has a .696 winning % Brady a .737, so advantage Brady clearly a lot depends on how the rest of Brady's career unfolds.