After the collapse in the Eastern Conference Finals last year versus the Toronto Raptors, the Milwaukee Bucks had several looming questions to answer. The biggest surrounding Khris Middleton, who was set to become a free agent after his first All-Star appearance.
Middleton had a sensational season for the Milwaukee Bucks, but it was up in the air if the forward could be a true second option on a championship-caliber team. The Bucks had faith in Middleton, though, rewarding him with a lucrative five-year, $178 million contract extension.
The move was criticized by many who believed Middleton was overpaid and undeserving of this deal, and that Milwaukee would eventually regret the deal.