Craig Counsell went to two WS as a player, both times with teams with little to no playoff experience who were playing against historic teams that were heavily favored to beat the crap out of them, and his teams won both times anyways, both on walkoffs, and Counsell was instrumental in both winning runs. Now he's managing a team with little to no playoff experience in a year when the AL team, whoever it turns out to be, is heavily favored to beat the crap out of the NL team.