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That's my final answer. One NLCS loss before he reupped one NLDS loss total in his 15 years with the Cubs. Wait, does it count even though he had 6 AB with the Phillies before going to Chicago?
In that case I'll change my answer to Todd Helton, no playoffs before extending. In fact 83 and 82 wins were the best until his 11th year when they went to the '07 series. Helton looks like the trump to me.