TL;DR: Browns suck at drafting talent on either side of the ball. And as this author suggests a weak supporting staff makes for failed Browns QBs.

The problem is everyone and everything around the quarterback. Jeff Garcia won a playoff game with the 49ers. Jake Delhomme almost won a Super Bowl with the Panthers. Trent Dilfer is the patron saint of the “bad QBs can win Super Bowls” argument. The Browns had them all and lost with them all because they are the Browns and not the 49ers, Panthers or Ravens. 

Source: http://www.theguardian.com/sport/blog/2016/mar/29/cleveland-browns-rober...