Embarrassing loss proves Giannis Antetokounmpo and Milwaukee Bucks championship window is closed

The Orlando Bubble was not good to two-time defending NBA MVP Giannis Antetokounmpo and the Milwaukee Bucks last season.

They were swept by the Miami Heat in the Eastern Conference Semifinals, leading to speculation that the Greek Freak might seek out a new host city moving forward in his career.

Instead, the Greek Freak surprised the masses by signing a five-year, $228.2 million max extension with Milwaukee in December. That decision enabled the Bucks to pull off a blockbuster trade for Jrue Holiday while Antetokounmpo opted against hitting the free-agent market this summer.

Fast forward several months, and the Bucks are now on the brink. They stood absolutely no chance in Game 2 of their Eastern Conference Semifinals series against the James Harden-less Brooklyn Nets in the Big Apple Monday evening.

The Nets found themselves up 17 after the first quarter and boasting a 24-point lead heading into the half. At that point, Giannis had attempted as many shots as veteran big man Brook Lopez. He was also on the receiving end of a highlight-reel play from Nets forward Blake Griffin.

When all was said and done at the Barclays Center Monday evening, Milwaukee found itself in a 2-0 series hole following an absolutely humiliating and deflating 125-86 loss. The next few games (if the series goes that far) is now going to represent a defining moment for Giannis Antetokounmpo and his tenure with the Milwaukee Bucks. Here’s why.

Milwaukee Bucks lack of playoff success with Giannis Antetokounmpo

Giannis Antetokounmpo, Milwaukee Bucks
Sep 6, 2020; Lake Buena Vista, Florida, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) looks on from the sideline after an apparent injury during the first half of game four of the second round of the 2020 NBA Playoffs against the Miami Heat at ESPN Wide World of Sports Complex. Mandatory Credit: Kim Klement-USA TODAY Sports

Despite his otherworldly performance since entering stardom during the 2016-17 season, the Bucks have not had much postseason success with the Greek Freak leading the charge.

This has very little to do with his performance. That must be noted before you come to the conclusion that we are throwing Giannis under the bus. Rather, it’s been primarily about a lack of a supporting cast and struggles from role players. Whatever the reason, it has not been great.

  • 2016-17: Lost first round to the Toronto Raptors (4-2)
  • 2017-18: Lost first round to the Boston Celtics (4-3)
  • 2018-19: Lost conference finals to the Toronto Raptors (4-2)
  • 2019-20: Lost conference semifinals to the Miami Heat (4-1)
  • 2020-21: Down in conference semifinals to the Brooklyn Nets (2-0)

One might think that the Bucks were set to ascend into legit NBA title contention after a trip to the Eastern Conference Finals against Kawhi Leonard and the Toronto Raptors back in 2018-19. Instead, the team seems to have regressed. Barring some type of unlikely turnaround in this series, that’s going to be taken to a whole new level.

Giannis Antetokounmpo did the Milwaukee Bucks a solid by signing extension

This can’t be lost in everything. Rumors had persisted leading up to Giannis signing said extension that he was eyeing larger markets. The Golden State Warriors and New York Knicks came up as potential destinations.

Likely due to the fact that he received more money on an extension with the Bucks and some sort of loyalty that’s uncommon in today’s NBA, Antetokounmpo pushed back against that. It might not have been his best play.

Sure it’s too early to even initiate suggestions that Giannis might end up asking to be traded. But right now, things are not looking great for the Bucks in what promises to be an ultra-competitive Eastern Conference moving forward. That brings us to our final point.

Premature playoff exit will lead to more questions about the Milwaukee Bucks

Giannis Antetokounmpo, Milwaukee Bucks
Mar 29, 2021; Los Angeles, California, USA; Milwaukee Bucks guard Jrue Holiday (21) and forward Giannis Antetokounmpo (34) react against the Los Angeles Clippers during the second half at Staples Center. Mandatory Credit: Gary A. Vasquez-USA TODAY Sports

Outside of struggles in the first two games against an elite Nets team, there’s another overriding concern in Milwaukee right now. Just look at what the Bucks gave up to acquire Holiday from the New Orleans Pelicans in the aforementioned blockbuster trade last winter.

  • 2020 first-round pick
  • 2025 and 2027 first-round picks
  • 2024 and 2026 first-round pick swaps

New Orleans now has control over four of the Bucks’ next seven first-round picks. Remember, the Houston Rockets own Milwaukee’s first-round pick in 2021 stemming from the P.J. Tucker deal ahead of the March 25 NBA trade deadline.

None of this is to say Holiday isn’t a good player. He is. He’s actually been a darn good fit with Giannis Antetokounmpo and the Bucks. Rather, it’s about a lack of flexibility to improve this roster moving forward. The four-year, $135 million extension Holiday signed with Milwaukee back in April adds another layer to this.

Just look at what the Bucks’ top players are going to earn over the next couple seasons. It’s astonishing for a team that has proven it’s not on the same level as the Nets.

  • 2021-22: Giannis Antetokounmpo ($39.35 million), Khris Middleton ($35.5 million), Jrue Holiday ($31.05 million)
  • 2022-23: Giannis Antetokounmpo ($42.49 million), Khris Middleton ($37.95 million), Jrue Holiday ($33.54 million)

Without draft picks to entice teams to take a bad contract and existing over the NBA salary cap, the Bucks are clearly in win-now mode. They must make a run in these playoffs to quiet concerns over Antetokounmpo’s future in Milwaukee.

Based on what we’ve seen through the first two games of this Eastern Conference Semifinals series, that’s highly unlikely to happen.