Pre-2019-20 Rank: #19, Pre-2020-21 Rank: #13, Pre-2021-22 Rank: #11, Pre-2022-23 Rank: #11, Pre-2023-24 Rank: #12.
*Peak Period: 2014-15 to 2020-21
When Damian Lillard joined the Milwaukee Bucks in 2023, it ended the run of one of the best players the Portland Trail Blazers ever had. In Portland, Dame was a six-time All-NBA Selection (one First Team, four Second Team, and one Third Team), and from 2017-18 to 2020-21, finished in the top eight in MVP voting. With that said, Lillard could only reach one Western Conference Final, and frustration naturally ensued.
Milwaukee was supposed to be Lillard’s best chance at an NBA Championship, but his pairing with Giannis Antetokounmpo did not result in much for year one. Like Paul George (who is above Lillard by one spot), a title will make the difference between first ballot and a bit of a wait.