I think the biggest thing Kraft wants is a HOF induction before he dies. Which honestly, probably would happen if he just shut the **** up for awhile.
Kraft already took a team with one SB appearance and got 10 out of them and 6 wins. He made the Patriots the most relevant team in the league for 20 years. Nobody longterm is going to care about slippage near the end of his run.
People bring up Landry's dominant run, they never talk about how bad he was when Jones fired him.
The truth is Kraft, Belichick, and Brady had their legacy in stone pretty much from the moment the run ended at the end of the 2018 SB. Brady got a little boost by doing what Montana never did and what Manning needed to be carried to in Denver. But everything else... nobody is going to really hold anything against them longterm for not winning more after already setting the bar.
Kraft did what every single owner dreams of doing, Belichick did what every coach wants to do, and Brady did what every QB wants to do. Most of them aren't even delusional enough to think getting halfway there is a failure.