James urged Theo to sign Ortiz in 2002 and not to sign Crawford (Ben C and Tippert pushed for Carl).

Tippett and James disagreed on whether the club should sign Carl Crawford. The former said his defensive ability would not be reduced because of the short left field at Fenway Park, the latter said it would. So far, Tippett said, James has appeared to have read things better -- but added it's too early to judge.  What Tippett stressed, though, is how often the front office disagrees: always.   "I always find it interesting that the public debate is always a lot more simplistic than the private debate," Tippett said. "The public debate was, 'Did it work or didn't it?', and if it didn't, 'Who should we fire?' 2012

Prior to the 2013 off-season John Henry stated the following:

… as Henry informed the Herald, James had fallen “out of favor over the last few years for reasons I really don’t understand. We’ve gotten him more involved recently in the central process and that will help greatly. He’s the father, so to speak, of baseball analysis and a brilliant iconoclast who looks at things differently from everyone else.”