It doesn't always work like that. Theoretically it should, as if he can do well with lesser players then he should be capable of doing better with more talented players, but there are other factors. Some managers just suit being the underdogs and working with lesser expectations more than they do managing star players with more pressure and expectations. Benitez is a good example of this. He did well with Valencia and Liverpool but when he took over Inter he struggled and did not do as well as people thought he would. People thought he would do better than he did at Liverpool and Valencia due to him having the best group of players in the league he was working in for the first time in his career, but it did not work out that way at all. Another example is Mourinho being able to win the CL with Porto but not with Chelsea or Madrid, despite having several attempts. Mourinho has shown in his career that he can win with both the underdogs and the favourites so I am not saying he struggles with pressure or anything, but the fact that he couldn't win the CL with Chelsea or Madrid and could win it with Porto shows that it is not as easy to win with big clubs is it is made out to be.
For what it is worth, I think Simeone would be a success if he had more money and more pressure at a club like Madrid, Bayern, Barcelona, Chelsea or if Atletico had more money to spend. I am just saying that him being more successful than he has been at Atletico so far if he had better resources is not as straightforward or guaranteed like some people seem to think. I cannot say for sure if he would do well and be more successful with greater resources and better players as he has been with Atletico and neither can you or anyone.
