The consensus here seemed to be very positive on these guys when picked up but its hard to know exactly when a player overstays their welcome. Some on here even wanted Judge to leave in FA to get that comp pick. What would the Yanks have looked like the past few years if he signed with Oakland out of HS?
The consensus doesn't mean much of anything really though. You, me and everybody else not named Brian Cashman aren't employed by the NYY and not receiving multi-million a year in salary to build the team. While we can all get giddy about a shiny new toy, Cashman has to be the adult in the room and say maybe somebody like Stanton is not needed and they can allocate those funds elsewhere. He's the one paid to get it right. The buck stops with him.
You can look at any one move and excuse it away, say "it seemed like the right/good decision at the time", "can't fault him for that move" and I don't general bash a GM on one move that ends up bad, but at some point, when the GM has a body of work big enough, you have to look at the whole picture. For all the moves that Cashman made that "seemed positive" at the time, too many of them have turned up not working out.