Like it or not, the work of a GM tends to get judged in hindsight.
And in hindsight, DD did a pretty poor job this year.
He signed Eovaldi and Pearce and that was basically it.
He did next to nothing about starting pitching depth or the bullpen.
And he put us in a position where the late season 'additions' to the lineup were Gorkys and Owings.
I suspect that Henry was comparing this to what Cashman did, which was to provide incredible depth to a team that was decimated by injuries but still ran away with the division.