9. Tom Thibodeau
Tom Thibodeau's 32-year coaching career has been filled with many stops, including the Rockets, where he spent four seasons as an assistant coach under Jeff Van Gundy from 2003-2007. Thibodeau had a full-circle moment when he became the head coach of the Minnesota Timberwolves and faced off against the Rockets in the 2018 postseason.
The Rockets demolished the Wolves within five games, but the bigger story was the Wolves returning to the postseason after a 13-year drought. Jimmy Butler was a large reason for the Wolves' success in that 2017-18 season, as he averaged a team-high 22.2 points, along with 5.3 rebounds and 4.9 assists.
However, Butler had worn out his welcome by his second season and requested a trade out of Minnesota. Thibodeau, who also served as the President of Basketball Operations, was the bottleneck in any Butler deal, as he was the ultimate decision-maker.
The Rockets, who had a Hall of Fame duo of James Harden and Chris Paul, tried nabbing Butler from the Wolves in 2018-19 and even offered a whopping four first-round draft picks, although to no avail.
Thibodeau seemed hellbent on trading Butler out of the conference and instead sent him to the Philadelphia 76ers in exchange for Robert Covington, Dario Saric, Jerryd Bayless, and a 2022 second-round draft pick.
This was essentially Thibodeau giving the Rockets the middle finger, as that offer was significantly worse than what the Rockets were offering.