Damian Lillard traded to Bucks: Big questions after the most shocking deal of the NBA offseason

Wow … what?

After nearly an entire NBA offseason of stasis between the Portland Trail Blazers and Miami Heat, superstar point guard Damian Lillard has been traded to the … Milwaukee Bucks!?

The shocking move — a three-team deal that also sent guard Jrue Holiday and 2018 No. 1 pick Deandre Ayton to the Trail Blazers and big man Jusuf Nurkic to the Phoenix Suns — doesn’t just dash the hopes of Heat fans, it creates an even more powerful juggernaut in Milwaukee led by two-time MVP Giannis Antetokounmpo, who now has another All-NBA talent by his side.

Did Milwaukee just become the unquestioned 2023-24 NBA title favorite? Which teams should be calling Portland about a deal for Holiday? Did Phoenix get better around its three stars? Where does Miami go from here?

Our panel of NBA insiders is breaking down what the biggest trade of the offseason means for all sides.

1. Lillard to the Bucks is _____.

Jamal Collier: League-altering. This move elevates the Bucks into superteam status, changes the conversation around Antetokounmpo’s impending future and sets the table for Lillard, after a decade in the league, to shine on his first true playoff stage with championship expectations.

Bobby Marks: Not risky. On the surface, trading for 33-year-old Lillard and the $200 million left on his contract is a huge gamble, especially considering Lillard has played a total of 87 games in the past two seasons. But when you factor in that the cost to retain Holiday could have reached $223 million on a new contract, the risk is mitigated. Also, if Holiday left next offseason as a free agent, Milwaukee had only the $12.9 million non-taxpayer midlevel exception to replace him.

Tim Bontemps: Stunning. I’m not sure it makes the Bucks much better, but it continues a trend of doing things that (seemingly) are designed to make Antetokounmpo happy. And if this helps him stay in Milwaukee long term, it’s an unquestionable win.

Dave McMenamin: Clyde Drexler-esque. After 10-plus years as the Blazers’ No. 1 option without reaching the championship mountaintop, Drexler was traded to Houston in 1995 to team up with the game’s most impactful big man in Hakeem Olajuwon to help Houston win a second ring (and his first). Nearly three decades later, Lillard could follow the same script with Antetokounmpo in Milwaukee.

André Snellings: An absolute game-changer. The Bucks have been my preseason favorites to win the championship in each of the past three seasons, but after winning in 2021 they have been really impacted by the injuries to All-Star second option Khris Middleton. Giannis is the most dominant player in the NBA and their team defense is tough, but they lacked the volume shooting from distance to be able to properly maximize their potential. Lillard gives them the best shooting-scoring option on the perimeter east of Stephen Curry — and on paper makes their team appear to be unstoppable in the East.

2. Antetokounmpo should feel _____ right now.

Collier: Powerful. His words carry weight. After Antetokounmpo cast doubt on whether he will stay with the franchise long term, the organization responded by pairing him with the best player he has ever called a teammate.

Bontemps: Satisfied. Giannis has talked openly about wanting to see the Bucks fully committed long term. This trade costs the Bucks a key option in Holiday and a ton of tax dollars. Now, let’s see whether Antetokounmpo can lead the Bucks back to the promised land.

Snellings: Elated, like he just got another 50-piece Chick-n-Mini meal after winning Finals MVP. Giannis has been holding the Bucks’ feet to the fire to make championship moves, and this is about the biggest move possible. Add in Lillard’s ultracompetitive “Dame Time” attitude on top of the incredible talent fit and it’s hard to imagine what else Giannis might be looking for before committing to an extension. The Bucks have shown they are all-in on helping him win more chips in Milwaukee.

McMenamin: Determined. The 2021 Finals MVP is adding a player who last season averaged 32.2 points (a career high) and 7.3 assists and shot 37.1% from 3 to a Bucks group that already had a momentous summer by re-signing Brook Lopez, seeing Bobby Portis gain big-game experience with USA Basketball and allowing more time for Middleton to return to form from his knee injury. Antetokounmpo couldn’t have asked for more from the front office.

Marks: Ready to put pen to paper. We wrote about how Giannis likely not signing a three-year, $169 million extension before Oct. 23 was a business decision. Especially with the uncertainty of Holiday entering the last year of his contract. Does that change with the addition of Lillard? Tacking on an extra three seasons would align Antetokounmpo’s contract with that of his new star guard.

3. Fact or fiction: Milwaukee is now the 2023 title favorite.

Collier: Fact. Losing Holiday hurts, but the Bucks have what they have been missing the past few seasons, a bona fide perimeter star who can pressure a defense off the dribble and score from the outside. Lillard will help Milwaukee avoid its most stagnant offensive tendencies. And if Lillard and Antetokounmpo can get on the same page in the pick-and-roll, there is no better combo in the league.

Marks: Fiction. I am not ready to crown Milwaukee the favorite even with the addition of Lillard. There are questions with their depth, especially at point guard. And losing a shooter in Grayson Allen hurts. And which Middleton is Milwaukee going to get this season: the All-Star from 2020-21 or the one who averaged 15.3 points in 2022-23?

McMenamin: Fiction. I’m not so sure the Bucks moved their championship meter any more than Phoenix did in this very trade by adding depth and another capable big in Nurkic, while parting with only one rotation piece in Ayton.

Bontemps: Fiction. How much of an upgrade is Lillard from Holiday? He’s obviously a tremendous player, but I’m not sure he’s a better fit for the Bucks. And there’s still Boston and Denver, among others, to worry about.

Snellings: Fact. I had them as the slight favorites pre-trade, in a close battle with a handful of other teams, including the defending champion Nuggets and new-look Celtics. With this move, health- and chemistry-dependent, the Bucks have by far the best team in the NBA on paper, with potentially the most difficult to guard duo since Shaq and Kobe — plus a raft of other talented players who know their roles.

4. Which team should be on the phone with Portland to get Holiday now?

Marks: Philadelphia. The 76ers can sit in a holding pattern and wait until the 2024 offseason when they can sign Holiday outright with cap space, but considering that the goal is to win right now, Philly should be drawing up Holiday trade options. The challenge comes with the reluctance of Philadelphia parting ways with guard Tyrese Maxey and the lack of appetite of Portland to take back James Harden. As with Wednesday’s Lillard blockbuster, the 76ers might need to rope in a third team to facilitate a Holiday trade.

Bontemps: About half the league, including Miami and the LA Clippers. Again, getting Holiday instead of Lillard would not be a bad Plan B. What’s certain is Holiday is going to be changing teams again at some point in the next few months. The only question is when.

Collier: Miami could rebound nicely by acquiring Holiday, although Jimmy Butler might need to apologize for the way he treated him during their playoff series in the first round last season. Another team who could really use a player like Holiday: the Chicago Bulls, who have been searching for a way to fill their point guard void with Lonzo Ball injured.

McMenamin: Miami. Holiday’s defensive-first mentality and noted professionalism will be a natural fit with the vaunted Heat Culture. If the Blazers and Heat can push aside any static built up between them from the Lillard negotiations that ultimately went nowhere, they might just find that there’s another point guard trade on the table.

Snellings: The Celtics should be either talking or on hold with the Trail Blazers. Boston has been a true point guard away from championship contention for the past two seasons, and it created a perimeter defense hole by trading Marcus Smart this summer. Holiday would fill both needs perfectly, running the team on offense and helping Jayson Tatum, Jaylen Brown and Kristaps Porzingis form into the potent offensive force they have the ability to become.

5. With the added depth, the Suns will finish _____ in the West?

Marks: I already had them as the second-best team, behind Denver, before the trade. I am not ready to insult the defending champions, but the additions of Allen and Nassir Little balance out a bench that was littered with players signed to the veteran minimum. The question for Phoenix is whether Allen is there long term, especially with Eric Gordon on the roster. Allen is in the last year of this contract and will be a free agent next offseason.

Bontemps: In the top four, probably. I’m not sure this deal helps Phoenix much, either. The Suns do get some depth options with cheaper deals, but none of this really moves the needle for me from a championship-contention standpoint. Other than Nurkic, if any of these guys is playing key minutes deep in the playoffs, it’ll be an issue, and Nurkic is a downgrade from Ayton.

McMenamin: Clearly Bontemps and I disagree on this one. The added depth from the trade will help coach Frank Vogel navigate the 82-game grind with some urgency, knowing he has backups to go to, rather than feeling the need to swaddle his stars in Bubble Wrap. Phoenix should be vying for No. 1 in West.

Collier: Top two. Denver is going to be right there with Phoenix at the top of the standings, but the Suns did well this offseason building a team around their superstars. Even if one of their stars has to miss time, the Suns have enough supporting cast and balance to make up for an absence from one of their top three players.

Snellings: With the added depth, the Suns will finish much higher in the West than they would have before. I was very concerned about the age and injury history of their three best players, all perimeter volume scorers, and the lack of defense, size and depth behind them. For what they need, Nurkic might be an upgrade on what Ayton could have given them inside, and the impact of the quality depth on the perimeter can’t be overstated. I still have the Nuggets as the favorites out West, but now would put the Suns on the level with the Lakers and Warriors as contenders, just ahead of the Kings and Grizzlies.

6. On a scale of 1-10: How much will Miami regret not dealing for Lillard?

Marks: One. It takes two to tango when making a trade. Portland simply felt Miami did not have the players or draft picks to make a deal.

Bontemps: Three. Sure, the Heat would like to have Lillard, but they always expect another player to become available. By this time next year, several more might hit the trade or free agent markets. Miami didn’t need to rush into any deal.