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.

Pre-2019-20 Rank: #18, Pre-2020-21 Rank #17, Pre-2021-22 Rank: #19, Pre-2022-23 Rank: #20, Pre-2023-24 Rank: #23.

*Positional Notes:  Love has also played a significant time at Center.

*Peak Period: From 2010-11 to 2016-17.

It is safe to say that Kevin Love is nearing the end of his career and has little time to add more accolades to his Hall of Fame resume, so if that is in fact the case, has he done enough?

Love was a three-time All-Star and twice a Second Team All-NBA player in Minnesota and was brought in to be the third piece to LeBron and Kyrie in Cleveland.  It worked, as the Cavaliers won the Title in 2016, but it also exposed Love as somewhere between role player and All-Star.  His ceiling might be post-career acknowledgments from Minnesota and/or Cleveland.

Pre-2019-20 Rank: #15, Pre-2020-21 Rank: #14, Pre-2021-22 Rank #14, Pre-2022-23 Rank #14, Pre-2023-24 Rank: #15.

Peak Period: 2014-15 to 2020-21.

For many years, Kyrie Irving has been the most polarizing player in Basketball, and at times, all North American sports.  It has never been about his play, as he is a multi-time All-Star, a three-time All-NBA Selection at Point Guard who can take over a game.  He helped LeBron James win the NBA Championship in Cleveland, and when he wanted to be the alpha, he was primarily applauded when he became a Boston Celtic in 2017, but that was when things became weird for the former Uncle Drew.

Irving pledged to bring greatness to Boston, but despite two All-Star years (and no deep playoff run), he signed with their rival Brooklyn, where a super team formed with him, Kevin Durant, and James Harden.  The big three fell apart as quickly as they came together, with Irving’s Brooklyn run marred by his refusal to get the jab and alleged antisemitism.  Irving, who marches to his tune, may have alienated many fans, but he is true to his convictions, knowing that it would (and did) cost him millions in endorsements.  He would force his way out of Brooklyn and, in his first full year in his fourth team, the Dallas Mavericks, where, along with Luka Doncic, he went to the NBA Finals.

With all his past (and maybe future) controversies, Irving might have to do more than most to ensure a spot in Springfield, and if he adds a ring in Dallas, his biggest haters will struggle to keep him out.

Pre-2019-20 Rank: #14, Pre-2020-21 Rank: #12, Pre-2021-22 Rank: #7 Pre-2022-23 Rank: #6, Pre-2022-23 Rank: #5.

*Peak Period: 2017-18 to 2023-24.

You could argue (and we will) that 2023-24 was the most disappointing season of Giannis Antetokounmpo’s career.  He was joined by Damian Lillard, arguably the biggest star he ever shared a court with, but Lillard and new Coach Doc Rivers were bounced in the first round and fell well short of expectations. 

Nevertheless, Antetokounmpo is a two-time league MVP and an NBA Champion who will turn 30 this year.  What does that mean?   The “Greek Freak” is in a prime position to add to his lofty resume, and since he is already a first-ballot HOF entrant, the only question is what his 30s will bring.  We would wager that will be an awful lot!