Questioned deal hires Monty Williams as head coach

The biggest mistake: Hiring Monty Williams as head coach (2023)

In four seasons with the Phoenix Suns, Williams made the finals, won the Coach of the Year award and won 63% of the games. He is a highly respected coach and a long-time NBA spokesperson.

But his tenure in Detroit was a disaster, and he was hired shortly after the Suns fired him after the second round of the playoffs. Given the biggest coaching contract in NBA history at the time ($78.5 million for six years), Williams didn’t seem to have mastered the strengths and weaknesses of new players, and his rotation was incredible. He slams his players in public. His two teams squeezed the Pistons' space. He started the draft, beating promising sophomore Jaden Ivey

Amid all this turmoil, Detroit set a record 28-game losing streak, ending its worst record in team history with a 14-68 record. This is not just a lost season, but also a regression for a team that needs momentum to move forward. The situation became so unsustainable that Williams was fired after the season, even though he still owed $65 million.

If anything, in retrospect, Williams' tenure looks worse. Williams’ replacement J.B. Bickerstaff, who finished second in the Coach of the Year vote, cleaned up Williams’ mess, led the Pistons back to the playoffs and helped Cad Cunningham grow into the All-Squad.