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Roundtable: Processing the Damian Lillard trade

The Brew Hoop staff talks Dame, Jrue Holiday, and the aftershocks of a major move

Milwaukee Bucks v Portland Trail Blazers Photo by Garrett Ellwood/NBAE via Getty Images

Welcome back to yet another year of the Brew Hoop Round Table, where we ask that everybody use coasters and please don’t feed the aging pugs from the table, thanks. With Damian Lillard officially on the roster and media day behind us, let’s take a breath and see how the staff feels about everything that has happened since the seismic trade.

What was your initial reaction when the trade news broke?

Alex: Surprised. Right? If the Bucks were going to make a big trade before the season, it was always going to be for an offensive upgrade. I had already made a case for a Jrue Holiday-DeMar DeRozan swap, but little did I know the real trade would actually involve more shooting. There’s no precedent in franchise history for adding a player like Dame Lillard, so “surprised” felt like the correct median between joy-addled delirium and quiet, mind-blown contemplation.

Van: Complete stupefication. Even an offer that wasn’t quite Miami’s best (no Caleb Martin, for example) seemed better than Milwaukee could offer. Other teams—namely Toronto, Brooklyn, Philly, and even Chicago—who were rumored to be in on Dame could put together even better offers. I still cannot believe that Blazers GM Joe Cronin opted for the Bucks’ package, seemingly out of spite for the Heat, which I certainly can identify with. Thanks to this trade, Cronin instantly became the third or fourth-best GM in Bucks history.

Morgan: Concern that something terrible had happened, thanks to the number of texts that I received that said “holy s***” with no context. But then stupefaction.

Kyle: LMAO I thought it was a joke at first but very happy.

Michael: When I saw the first tweet from Shams, I quickly scanned the profile to make sure that I wasn’t being trolled. I’ve been bamboozled by sports Twitter too many times to take any sort of news at face value. But after I verified the source, I was stoked! I spent the next 10-ish minutes neglecting my work and texting anyone who would listen about how crazy the news was.

What immediate on and off-court effects do you anticipate?

Alex: Greater focus on the pick-and-roll and a more efficient half-court offense, but somehow fewer alley-oops. They’re a triviality, for certain, but the Bucks attempted 93 oops in total last season compared to the Portland Trail Blazers’ 58 attempted oops, according to statistics from the NBA. Perhaps this will mean a more controlled, concerted offense, which would likely mean less “give Giannis the ball and let him do things” and more deliberate execution.

Off the court, Dame will shoot at least one music video in Milwaukee. Personally, I’m hoping the Bronze Fonz statue is included in the storyboard; please sound off in the comments about which other local landmarks need to be featured.

Van: A significant uptick in the halfcourt offense’s production. I don’t even think it matters what the new coaching staff (namely Terry Stotts) draws up, because as Zach Lowe said last week, Dame is a top-five halfcourt offense on his own. While Milwaukee’s postseason numbers in the halfcourt have been awful for years, their regular season numbers took a real dive last year without Khris Middleton. With now two outstanding P&R ballhandlers paired with two outstanding roll men in the starting lineup, I expect the Bucks’ to be at least near the top of the league in points per possession in pick & roll.

Morgan: I’m excited to see what Dame looks like as a #2 option. He’s been the guy for his entire career. Can the presence of Giannis cancel out—or even overcome—the specter of age? I’m similarly excited to see what Khris looks like as the #3. His production should improve with more space to take on lesser defenders. And it’s not immediate, but I look forward to having a functioning offense in the playoffs! Thankfully, we have an experienced head coach who can... oh wait.

Off the court, Dame is a class act, a loyal star who stayed with a small-market franchise until they decided to rebuild. He has the hardware to prove it too: he won the J. Walter Kennedy Citizenship Award for the 2018–19 season, awarded for “outstanding service and dedication to the community,” and he won the Twyman-Stokes Teammate of the Year Award for the 2020–21 season, awarded for “selfless play and commitment and dedication to his team.” The only other player to win that award over the last four seasons? Old friend Jrue Holiday. As someone whose fandom is comprised in part by the apparent quality of folks on the team, I will find it easy to root for Dame.

Kyle: RIP to the Mickey Mouse Clubhouse offense that we saw sometimes. Off the court, well, you saw how Milwaukee reacted to Dame’s arrival at the rally. It is a bummer to lose Jrue.

Michael: I think it is safe to assume that the addition of Dame will solve a lot of the Bucks’ offensive struggles from late last year. Adding an outside scorer of his caliber will do wonders for the pick-and-roll game, and his gravity will create better offensive matchups for every non-big on the floor. The Bucks’ defense may experience some growing pains, but I don’t think it will be anything serious.

When all is said and done, where can Damian Lillard rank on the list of all-time greatest Milwaukee Bucks?

Alex: He has top-10 potential. Winning creates a lot of goodwill, but so do soundbites. Would a championship from Dame surpass the immortal “Bucks in six” mantra given to us by Brandon Jennings? I tend to think not, but there are differences between heroes and folk heroes, so I’ll hedge and say top 20, especially since he already intimated in his goodbye statement that he wants to wear a Portland jersey again before he retires.

Van: If he stays healthy and stays with the team for three seasons or so, the top twenty seems a given. If he contributes to one championship, top ten. More than one, top five.

Morgan: I’ll dodge this question by virtue of not counting chicks before they hatch. Certainly not because my knowledge of the top X Bucks is paltry.

Kyle: Uhh, higher than Charlie Bell and Gary Neal.

Michael: Like Van said, I think his ceiling is top five. If the team doesn’t win at least one title with Dame (god forbid), I don’t think he cracks the top 10 in the eyes of most Bucks fans.

What will you miss most about the Bucks’ Jrue Holiday era?

Alex: In the glimpses that fans and media caught of the team off the court, Jrue was often the foil to Giannis’ exuberant, goofy personality; the wry, composed individual you could expect to widen his eyes and shoot a glance toward the camera. For all the frustrating on-court moments, the continuity of the core roster over the past few seasons always gave me solace. Watching the team made me feel at home, thanks in no small part to Jrue and knowing how invested he was in his relationships with teammates, in his family, and in the community. Christmas will feel different this year—sometimes it just takes time to get used to the remodel.

Van: I’m actually not going to say his on-ball defense, as good as it is. While his perimeter defense certainly legitimizes Boston’s title chances and could make life difficult for Lillard and Middleton in a playoff series, he was too undersized to be Milwaukee’s primary option on opposing wings, as we saw in their last two playoff defeats. It will instead be his knack for making outstanding defensive plays in the clutch, particularly in the postseason. No one in the league has the skill or guts to strip an opposing ballhandler in a game’s closing moments.

Morgan: The day after the trade, my sister texted me twice: 1) “Why are the bucks trading Jrue Holiday,” and 2) “I like him.” My attempted explanation was greeted with a single letter: “L.” I couldn’t have said it better myself. It was an absolute pleasure watching Jrue work on defense, and although at times it was abject misery watching him on the other end of the floor, that made it all the sweeter when he inexplicably called his own number and came through (see: final minutes against the Nets). In addition to his three (!) Twyman-Stokes Teammate of the Year Awards, he won the NBA Sportsmanship Award for the 2020–21 season. Off the court, he and his wife have raised millions to uplift Black and Brown communities. All the while, he has been, in my eyes, the most attractive Buck. We’ll miss you, Jrue.

(But really? The Celtics?)

Kyle: Jrue was exactly what the Milwaukee Bucks needed on the court at the time of his arrival and showed countless times why Milwaukee made the gamble for him. Obviously, we will remember the steal and lob in the Finals and stripping Marcus Smart in 2022. I also remember when it was he who sparked Milwaukee’s victory against Phoenix this past season, hitting clutch shots. He was also perfect for the city of Milwaukee at the time as his and Lauren’s work helped countless organizations with funding and awareness. It’s hard to lose not only a good player but also a good person and family.

Michael: I’m going to miss Jrue’s grit. As a team, the Bucks are really good about playing with tenacity, especially on defense. But I’m a sucker for a scrappy, high-motor defensive guard like Holiday. It doesn’t come easy for him; he wasn’t blessed with remarkable height. But he always gave it his all on both sides of the floor, and any team is lucky to have a guy like that. Unfortunately, the Celtics are feeling really lucky right now.

Please share any parting words and/or gifs for Grayson Allen.

Alex: Grayson’s story arc is a doozy, and for as much as I disliked him at Duke, I felt like his reputation as a dirty player was largely undeserved once he entered the NBA, to the point where I warmed up to him as a member of the Utah Jazz, actively rooted for him as a role player for the Memphis Grizzlies, and cracked a satisfied smile when he came over to the Bucks. The guy just wants to play video games and play basketball, and I mostly had fun watching him with this team whether he was starting or coming off the bench (no opinion on his adventures in gaming).

Van: Oh boy. I feel like a vocal section of the fanbase would discredit anything good that Allen did and focus only on the bad. Chicago series? Who cares, he stunk against Boston. This past spring’s Miami series? Who cares, he couldn’t get the final shot up. In both those series, he was sometimes asked to take on a role that was beyond his skillset, be it due to an injury to Middleton or other players getting cooked by bigger wings. Neither of those is in his wheelhouse, but the things he was good at he did very well, don’t get it twisted. He leaves as the franchise’s all-time leader in true shooting and effective field goal percentage. That means something, even if some refuse to admit it. Fans applied a frustrating double standard with him: like all role players, even the best ones, they are by definition limited. With Allen those drawbacks sometimes came defensively—though he came a long way in that regard, becoming at least average last season—or offensively, like not taking enough threes or being a very effective driver. But he took tons of criticism because... reasons? Like Badger fans still being mad about the national title game in 2015 (something I got over) or transgressions in his first few pro seasons. Meanwhile, Bobby Portis was played off the floor by a key opponent in each postseason as a Buck and he gets no such shade. I couldn’t stand the unreasonable Allen hate, and I’m relieved that it will leave town with him.

Morgan: So long, and thanks for actually making threes in the playoffs!

Kyle: Thank you for that Chicago Bulls series. It’s also not your fault that you had the ball that late in Game 5.

Michael: Best of luck in Phoenix. Don’t let the door trip you on the way out!

True or False: the Bucks will clinch the No. 1 seed in the East this season AND win the NBA championship in 2024?

Alex: False. If anything, the Budenholzer era taught us that the No. 1 seed in the Eastern Conference is negligible in the end. With the new limits on load management and missing games, I think there’s a real possibility that we see several partially played games from the new Core Four in hopes of saving their legs for the playoffs at the sacrifice of top seeding.

Van: I’m going to say false, if only because I don’t think both of these will occur this coming year. Which one do I think is more likely to happen? I’ll actually go with the title because there is no star who is more motivated to get a ring than Lillard. Also, I think they’ll take it easy in the regular season, Boston is also really good, plus there will be growing pains between a new backcourt and a new coach. I’m fully prepared to be wrong about this in six months when they’re a 60-win team because their ceiling is certainly in that range.

Morgan: Bucks vs. the field? False. Bucks vs. other individual teams? Maybe. As alluded to above, I think this trade elevates my concern with Griffin. He’s not running back a team anymore; he’s crafting a team (admittedly with some spectacular pieces).

Kyle: True. F it, we ball

Michael: False. Don’t get me wrong, I have a lot of optimism for this season. But for Pete’s sake, this team still has a first-year coach. I think it’s likely that at least one of these things will happen (hopefully the second one), but I can’t confidently parlay them at this time.

Now it’s your turn! Let us know your answers to these questions in the comments below.