So I stumbled across the Bill James interview at Time (hat tip Tango) and found this nugget:
James: Everybody who is my age, or everybody who is over 30, knows that joke. I mean, I'm not sure I get the point of the over-shift against David Ortiz. It helps you if he hits a ground ball, but if the bomb goes off, you can put those infielders anywhere you want to, it doesn't really do you any good. The damage that David does comes when he hits the ball 380 feet. It really does not matter much where you put your infielders when that happens.
I have tremendous respect for James and his work, but this seems a little weak. What he's saying is by implementing the Ortiz shift the team is only aided if Ortiz hits a groundball, if he hits a homerun the shift does no good. Simply put that's common sense. Of course if Ortiz hits a homerun any defensive alignment is useless, but here's the thing; Ortiz only hits homeruns 16% of the time and he makes an out 62% of his at-bats, suggesting there is value in playing the shift.
This is a very small sample size, but take a look at Ortiz' 2007 hit chart at the Trop; nine groundouts, eight into the shift, one homerun. In 2006 he hit seven homers and hit into the shift eight times. Checking out Ortiz career Fenway numbers he's grounded out over 300 times, to the naked eye it appears to be split 60:40 if not more on groundballs hit to the right side. BR has Ortiz for 389 outs to the second baseman over his career, 313 to the first baseman, 183 to the shortstop, and 129 to third.
Does the shift prevent against Ortiz' homering? Of course not, and it's not the perfect solution to face Ortiz, however his balls in play data suggest that if Ortiz is going to make an out it's going to be beneficial to play the shift.