There's nothing that brings professional athletes together than shared adversity. And during the Milwaukee Bucks' run to the championship, the team certainly went through a ton of turmoil, forever binding the star trio of Giannis Antetokounmpo, Khris Middleton, and Jrue Holiday in the annals of NBA history after they hoisted the franchise's first championship in 50 years.
Alas, all good things come to an end, perhaps to bring further good down the line. That's what the Bucks did when they dealt away Holiday, their blockbuster acquisition in 2020 that proved to the team's final piece to the championship puzzle, to the Portland Trail Blazers in the deal that brought Damian Lillard to the Cream City.
Thus, it's not too difficult to imagine the remaining Bucks players in that 2021 title-winning squad feel a mixed bag of emotions in the aftermath of Jrue Holiday's departure. Khris Middleton appears to be one of the players who'll miss Holiday the most, as the Bucks forward posted a picture of him and his now former teammate in their 2021 NBA Finals postgame presser on his Instagram story.
Khris Middleton also said goodbye to Grayson Allen, another piece the Bucks trade that's proven to be instrumental to the team over the past two seasons. Allen, of course, was not yet on the team during the Bucks' championship-winning season, although he did play a huge role in very good Bucks teams in both 2022 and 2023. However, the last memory Bucks fans will have of Allen is him failing to get a shot off in time during the 2023 NBA playoffs as the team suffered a first-round exit to the Miami Heat.
Trading for Lillard will certainly be bittersweet for Middleton, as he's been through plenty of ups and downs with both Jrue Holiday and Grayson Allen. There will be an added tinge of heartbreak given that Holiday declared his love for the Bucks franchise just a few days ago, even going as far as saying that it'll be an honor for him to retire with the team. Now, the hope now for both Middleton and the Bucks is that the sweet far outweighs the bitter.