No. 2 – The Jrue Holiday trade
After three brutal playoff exits, it was clear that the Milwaukee Bucks needed to move on from Eric Bledsoe, who struggled in all of them. The Bucks were heavily shopping the guard around the league in hopes of getting an upgrade. For a while, it seemed like the team was stuck, but that all changed on a historic November night in 2020 when a blockbuster four-team deal went down.
On November 23, the Bucks traded George Hill to the OKC Thunder while sending Bledsoe, three future first round picks, and two pick swaps to the New Orleans Pelicans for Jrue Holiday and the draft rights to Sam Merill in a deal that also included the Denver Nuggets. It was a major move for the Milwaukee Bucks, who paid a hefty price for an upgrade in the backcourt.
Yet, in addition to simply getting Holiday, this deal was also about assuring Giannis that the team would do everything possible to win a title. Indeed, the Greek Freak thought it was enough, as he inked a massive five-year extension shortly after that move went down. Sure, the Bucks gave up a ton for Holiday, but Antetokounmpo’s extension and what came soon after made it all worth it.
Upon arriving, Holiday instantly clicked with his new teammates. He provided excellent defense, which earned him a First Team All-Defensive nod that season. He wasn’t too shabby on offense either, serving as the perfect third piece next to Antetokounmpo and Middleton. Yet, the true test would be the NBA Playoffs, where history happened.
In his first playoff run with the Bucks, Holiday had his share of ups and downs with the Bucks, but he always came through when it mattered. Whether he made timely buckets or one of the most iconic defensive plays in NBA Finals history in Game 5 versus Phoenix, the guard was a key cog in helping the Bucks win it all in 2021.
Over the past two seasons, there’s no denying that Holiday has had his share of playoff struggles. Still, even then, the team would make this trade again 10 times out of 10. Holiday has been vital in making this iteration of the Bucks contenders at a time when the franchise desperately needed an instant shot in the arm. He was the best trade acquisition in recent memory up until very recently.
Though he’s no longer in town, he’ll still be remembered as the ultimate needle mover in 2020-21.