The 10 Wildest what-if scenarios in Milwaukee Bucks history

7. Keep Ray Allen

Allen became a star with the Bucks. Milwaukee drafted him fifth overall in 1996 and instantly made him their starter. Allen was an elite shooter from day one and transformed into an All-Star by year four. He made third-team All-NBA in 2001 but was shockingly traded during his seventh season in Cream City.

It is easy to forget that the Bucks made the conference finals in 2001 with Allen as their leading scorer. They lost to Allen Iverson and the 76ers in seven games and failed to make the playoffs the following year. The relationship between the Bucks' star and head coach George Karl deteriorated, which led to this stunning deal.

Jesus Shuttlesworth was an All-Star in six of the next seven seasons and played a key role in the Celtics winning the championship in 2008. Allen added a second title with the Heat in 2014 before retiring after 18 years in the NBA. He shot 40.0 percent from 3-point range and is second all-time in threes made behind only Stephen Curry.

The Bucks did not win another playoff series until 2019. They had a star in his prime and decided to trade him for a 34-year-old Gary Payton. It was a massive misstep by Milwaukee and keeping Allen would have certainly changed plenty for the Bucks during that era.