Bill Simmons delivers cold hard truth about Giannis trade dilemma

They simply haven't played in enough big games since the title run.
Milwaukee Bucks forward Giannis Antetokounmpo reacts after scoring a basket in the third quarter against the Indiana Pacers at Fiserv Forum on December 13.
Milwaukee Bucks forward Giannis Antetokounmpo reacts after scoring a basket in the third quarter against the Indiana Pacers at Fiserv Forum on December 13. | Benny Sieu-Imagn Images

Winning has always been Giannis Antetokounmpo's primary goal with the Milwaukee Bucks, and there simply hasn't been a lot of it lately, as pointed out by sports analyst Bill Simmons. On a recent episode of the Bill Simmons Podcast, the analyst highlighted how the Bucks have only won eight playoff series in the Giannis era, including just one after the title.

"He's only had eight playoff series wins. I'm going to put that into perspective. LeBron [James] has 41. Tim Duncan has 35. Kobe [Bryant] had 33. Shaq [O'Neale] had 32. [Kevin] Durant 22... I think he's just looking at this like 'I just want to be in the playoffs. I want to keep playing past April 30.' I think it's really starting to get to him."

Winning more makes all of this go away for Giannis, Bucks

It must be added that four of those eight playoff series wins came during Milwaukee's 2021 title run. Outside of that year, this team hasn't had much luck in the NBA Playoffs. In fact, since the title, they've won just one playoff series, which came against the Chicago Bulls in 2022. For the last three seasons, they've lost in three consecutive first rounds, including one as the top overall seed.

Now, it would be foolish to sit here and act like the Milwaukee Bucks have done this much losing lately simply because they haven't been good enough. Even if the rosters weren't perfect, injuries have hurt this team mightily. Khris Middleton, Damian Lillard, and yes, even Giannis Antetokounmpo, all missed time in these playoff matchups due to injuries. It's hard to win when the best players are out.

Giannis finally got a taste of what winning was like during the title run. With his chances of making the NBA Finals in 2019 ripped away from him in heartbreaking fashion against Toronto, he finally got back on the right track and went all the way. As is the case with all competitors, he likely got attached to the feeling, and it keeps him up at night that he hasn't made it back in almost a half-decade.

If the Milwaukee Bucks want to convince Giannis to continue the partnership, it all boils down to once again winning games and playing under the brightest lights. It's far easier said than done, but with this retooled squad, the Bucks are hoping that changing their identity will lead to more success after three straight years of shortcomings.

This season feels like it will be the ultimate test. A deep playoff run could change everything for the Bucks and turn the Giannis trade rumors on their head. However, a quick exit or early end to the year could have dire consequences. Everyone in that building feels pressure to put their best foot forward and help the Bucks get back on track.

Stay tuned for more Milwaukee Bucks analysis.