The Manny contract, which came with the team sold to JH was likely the best "large and long" deal the teams of the 2000's had. (Papi's 4 year deal is not really "long," and even that great deal that lead to 2 rings, ended very bitterly.
Take away the 4 year deals and how many deals were good to great start to finish?
How many were good for more than half the years?
Had AGon stayed with us and put up the same numbers, would that contract be called a good one?
While many of these deals were essential pieces to ring years, and that is a huge plus, not many really could be called clear winning deals. One might begin to understand why JH is reluctant about repeating the same mistakes over and over. Great business men are often known for not doing just that. They learn from their mistakes and try hard not to repeat them.
Had we extended Lester, large and long, that would have been in the "win column." Had we extended Jake, ERod and some others, not at all.