2003-2008 (6 years): 4 trips to the ALCS, 2 WS titles.....that's an A.
2009-2011 (3 years): 1 playoff appearance.....a D (a C in a smaller market).
Overall: with proper weighting (6 years vs 3), that's a B.
However, this discussion of grading made me think of a common concept used in subjective grading, which is what this is, that really applies here. Grading on a curve. Given the nature of the league, there are very good teams, good teams, mediocre teams, bad teams, and very bad teams (A, B, C, D, F) every year....or over a span of years. And, like in curved grading, I think it only fitting to be graded against your peers.....not absolute grading, which is graded against a perfect ideal, which doesn't exist in this population (MLB GM's).
On a curve, 10% of the "class" should get an A, 20% a B, and the remaining 70% a C or lower. B or higher means he's been one of the top 9 GM's in the league over his tenure. I can't think of 9 rock solid cases to move him into the lower 70%. Can you?
He's easily a B, with a strong case for an A, IMO. I think the disappointment of the last two years is eclipsing the success he had here. Only one other team has multiple titles over that timeframe (STL), but with more years missing the playoffs, and not as many trips to the LCS. Nobody has been the LCS as often. This stuff needs to stop being overlooked.