The list also includes Russell Wilson, and the punditry are particularly bothered by Deshaun Watson and Patrick Mahomes being available when the Bears were on the clock the time they hired Mr Trubisky.
It might be that Bear management made the right decision given the information they had at the time, e.g. "Mahomes was criticized for improvising too frequently and becoming too much of a risk taker whose desire to hit the big play created a habit of frequently throwing the ball into coverage and hoping for the best" and "Watson’s 32 career interceptions at Clemson were seen as a red flag. There were additional questions about his slender frame and ability to hold up physically against NFL defenders."
And yes, multiple teams passed on the opportunity to draft Tom Brady ("Can you imagine if the Bears had a 2000 draft class that featured Urlacher and Brady?") and Aaron Rodgers (the Bears were still relying on Rex Grossman calling signals, and Cedric Benson at running back was not a bad choice) and a number of the current playoff quarterbacks, including Drew Brees and Russell Wilson were written off as "too small."
My quandary, though, is a different one. Given the importance of the quarterback to a successful football team, and the multiplicity of Quarterback Prep high schools (and quarterback academies for middle-schoolers) and the efforts of colleges at all divisions (the current 49er quarterback, Jimmy Garoppolo, gave Northern Illinois fits in a cross-divisional game a few years ago, and he learned his craft as understudy to Tom Brady) why is there not a reserve army of underemployed quarterbacks ready to suit up and play at the professional level? You'd think tightwad owners constrained by free agency and a salary cap would do everything in their powers to take advantage of such a situation.