I don't think Weidman could beat Silva right now, or even in a year, but once Chris reaches his full potential and sharpens up his game I can see him beating Anderson. He has a scary blend of athleticism, wrestling and an extremely dangerous ground game, which are three major things you need to be able to utilize against Anderson. Working with Ray Longo and Costa Philippou, his striking is only going to get better. The area I see Weidman needing to work on the most is his explosiveness. The thing that worked for Chael so well against Anderson was his explosive double. Weidman doesn't have that. One small (very small) dent in Anderson's game is that he lacks a natural base what makes defending takedowns easier. If Weidman can develop an explosive double I can see him giving Anderson a very, very tough fight.
I dare say by the time Weidman is good enough to beat Anderson (if ever) that anderson will be pretty much retired.