No. 3 - Doc Rivers
Despite being ranked as one of the 15 greatest coaches in NBA history, Doc Rivers does not have the greatest track record. He did win a championship in 2008 with the Boston Celtics, but since then, his teams, typically full of star talent, have come up short. Notably, teams with Rivers at the helm have a history of blowing playoff leads, which has essentially become Rivers' legacy at this point.
Winning a championship with the Milwaukee Bucks would not undo his past coaching shortcomings, but it would certainly give Rivers' legacy a big jolt. It would show that he was not just a one-hit wonder who won with one of the best Big 3s of all time and that he was more than deserving of making that top 15 list.
Rivers would undeniably earn bonus points for taking the team over mid-season. There was certainly dysfunction for the Bucks early in Rivers' tenure, but if he can right the ship and help the team finish strong after the incredibly turbulent season they've had, it would only make a championship-winning campaign that much more impressive, similarly to the Cleveland Cavaliers in 2016.
The Bucks clearly believe in Rivers, dishing out a hefty paycheck to pry him away from his analyst job and get him to lead this team. Time will tell if it ultimately pays off.