The 10 Wildest what-if scenarios in Milwaukee Bucks history

The Milwaukee Bucks have won two championships and are planning on more. Giannis Antetokounmpo is the franchise’s latest all-time great. The Bucks are not afraid to be bold in improving their roster around the Greek Freak. They know how difficult it is to find a superstar, and Milwaukee is trying to maximize every season of his prime.

The Bucks won the title in 2021, but have been bounced in the first round of the playoffs in two straight years. After being upset by the Heat in 2023, Milwaukee traded for Damian Lillard. They focused on improving on the margins this summer and hope continuity brings success in 2025.

What if the Bucks never drafted Giannis? Milwaukee drafted two legends who never played for the franchise and almost traded for one of the biggest stars of this generation. Things would be vastly different in the 414 if any of these what-ifs actually happened.

10. Bucks trade for Bogdan Bogdanovic

Milwaukee knew they had to make moves in the 2020 offseason. They had just lost to the Heat in the second round of the playoffs and were searching for their first championship since 1971.

The Bucks made a bold deal to acquire Jrue Holiday and nearly acquired Bogdan Bogdanovic in a sign-and-trade. The pact was agreed to and announced days before free agency, which quickly became a problem. Bogdanovic had to wait before talking with teams, and the deal was suddenly off (subscription required). The Bucks even lost a future second-round draft pick for tampering, despite Bogdanovic never coming to Milwaukee.

He signed a four-year contract with the Hawks in free agency, but what happens if the deal went through? The Bucks went on to win the championship in 2021 without Bogdanovic. Does that still happen with him? It is impossible to say, but things may have been extremely different if this sign-and-trade had waited a few more days.