Lets be real here. When playing behind someone else, the job is to make everybody sound better than they are. We try to make the mediocre players good, the good players great. Doesn't matter what context of the music is. The higher the level, the higher expectation that you can hold the fort by yourself and not get lost. So if you prod and push and dish it out, you better be sure you're on strong footing. And it all depends on the playing context.
If Miles rose from the dead and asked to play a straight ahead gig with him, I think we'd all get fired if all we did was stick to chord tones and roots. He'd want to be pushed and prodded as it would be safe to assume that would be his expectation from what we know. Who I play with matters. I'm not going to play the same way if I were to play with Wynton vs. Ethan Iverson. They will demand different things and some want more prodding than others. Some will allow more freedom than others and have different expectations. Playing it safe all the time does not always work for your longevity to get called again for a gig.