Drought: 45 Seasons
Last NBA Title: 1971
The last time the Milwaukee Bucks won an NBA title Kareem Abdul-Jabbar was just coming off his rookie season and was still named Lew Alcindor. They also had a guy named Oscar Robertson who, despite being past his prime, was able to help Kareem bring a championship home to Milwaukee.
45 seasons later and the Bucks haven't felt championship gold since.
Recently, things seemed to be headed in the right direction for the Bucks after drafting core guys like Giannis Antetokounmpo and Jabari Parker, but last year they returned to the bottom tier of the Eastern Conference with an abysmal 33-49 record.
Although their strength is currently at the small forward position the Bucks, and the entire city of Milwaukee, would gladly welcome LeBron James with open arms if he could end their gruelling 45-year championship drought.