Can you handle a big salary?

I've noticed a relationship between salary size and inability to speak the truth. Essentially, how it seems to work is that well-paid senior management seem to be extremely choosy about the times they point out to their boss that they think something is a bad idea. They "pick their battles" and "build relationship" by saying yes. The other, rarely used alternative would be to present thoughtful, articulate and contrary advice. This advice is not invited, nor is it appreciated until it is appreciated.

I've tried to put myself in the position of these senior individuals:
A) They were hired to show results
B) The bureaucracy can at times be fickle and has demonstrated a hair-trigger response to employment issues in the past (read: they could get canned)
C) The salary they're now at is an increase for them... quite possibly the pinnacle of their career

I have trouble coming to the same apparent conclusion, though, that you have to play the game to get the odd win. I have a salary that is nothing to scoff at. In fact, I currently make double what I thought was wildly successful when I graduated university 10 years ago. I was naive, yes, but I'm still making well above average and more than I need.

I don't think you have to play the game and incrementally present a change of course. I think playing (and validating) the game guarantees we don't create value or effective results. Read The Wisdom of Crowds to become a believer.

There's clearly a deliberation that happens here. Individuals attain a pinnacle point, or at least the best so far in their career. The choice is to play safely and receive the paycheque or to stick to your principles and try and make meaning. It appears that with such big salaries on the line, the decision to play safely is just too tempting.

In one of the richest and most comfortable countries in the world, the excuse that you've got mouths to feed no longer cuts it. Is it the status, then? The trips and toys that can be bought? The validation of appearing in control? I find it hard to believe this stuff is better than making a meaningful result.

I might be seeing this all wrong. This also begs a question: Which came first? The sycophancy or the salary?