5 teams who will regret not beating Bucks' offer for Damian Lillard

Damian Lillard is heading to the Milwaukee Bucks... these five teams should have made a strong effort to avoid that outcome.

Damian Lillard, Jrue Holiday
Damian Lillard, Jrue Holiday / Abbie Parr/GettyImages
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The Milwaukee Bucks sent the NBA fandom into a frenzy on Wednesday afternoon, trading Jrue Holiday, Grayson Allen, and future draft capital to acquire Damian Lillard from the Portland Trail Blazers. After months of Lillard banging the drum for a Miami Heat trade, he ends up with the team Miami eliminated from the postseason, poised for a productive partnership with two-time MVP Giannis Antetokounmpo.

The two sides also roped in the Phoenix Suns, who sent beleaguered center Deandre Ayton to the Blazers in exchange for a gaggle of role players.

Dame trade

The Bucks are huge winners here. There is undeniable risk in dealing for a 33-year-old Lillard with four years and over $200 million left on his contract. The risk is offset, however, when the centerpiece of the deal is 33-year-old Jrue Holiday. There is also the Giannis factor. He has spent all summer threatening to leave the Bucks at the first sign of trouble. Dame reinforces the Bucks' focus on winning now — and winning big.

Milwaukee will enter the season as favorites to win the East, and maybe even the whole darn thing. Lillard is coming off the best individual campaign of his career — 32.2 points and 7.3 assists on 64.5 TS% — and he's the ideal pairing skill-wise for Giannis. Dame stretches defenses thin with his deep range; Giannis breaks them down the middle with his bulldozing drives.

Again, it is essential to emphasize how good Damian Lillard is. Much was said about his age, injury history, and the size of his contract. But this is Damian Lillard, a generational offensive talent who now joins the best team of his career.

The Bucks fanbase should be reveling in the streets. These teams, however, will probably come to regret their reticence upon watching the first Lillard-Giannis pick-and-roll.

5. Why the 76ers will regret not trading for Damian Lillard

Could the Philadelphia 76ers beat the Bucks' offer? That's the most important question here, and the answer is yes. The combination of Ayton, a former No. 1 pick, and Holiday (who the Blazers can flip for more assets) is a striking package, but it's far from the best superstar trade package in recent history.

The Sixers' only path to matching or exceeding the Bucks' offer would have been the inclusion of Tyrese Maxey. It's fair to question the logic of such a trade from both sides — Maxey is the Sixers' only real shade of youth, and the Blazers have too many guards already — but Maxey is a 22-year-old with room to grow. He is a better individual asset than Holiday or Ayton, and he would fit the Blazers' timeline.

The buzz all summer from Philadelphia was that Maxey is off the table for Dame or any other player. It's hard to argue with the Sixers' desire to keep such a promising talent in-house, especially with the volatility of the roster's older core. There's no telling when Daryl Morey will have to pivot to a rebuild.

On the other hand, the goal has to be to maximize Joel Embiid's title window. The Sixers can't afford to hedge their bets, because it will only result in more second-round exits. Losing Maxey would have been a tough pill to swallow and the risk would have been significant, but it's Damian Lillard. His 3-point shooting and halfcourt playmaking, paired with Embiid's scoring prowess inside the arc, would have established Philadelphia as Eastern Conference favorites. It may even have been doable without involving James Harden, who could either return for one last season under Morey or deliver more quality contributors to Philadelphia as part of a separate trade.