Milwaukee, WI
Roundtable: 2024–25 Milwaukee Bucks predictions
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. We’ve made it, folks. Milwaukee Bucks basketball is finally back—and with the return of the Bucks comes the return of the annual Brew Hoop season predictions. It’s always fun to collect thoughts before the season officially tips off and look back at them at the conclusion of the year. We’ve tried to spice it up a bit with some different questions than in years past.
Bucks 2024–25 Record, Seed, and Playoff Performance
Gabe: With Boston coming off their championship as the clear favorites in the East, the Knicks bolstering their squad, Paul George coming to Philly, and the Pacers making a playoff run last year, this is the first season in which it really feels as if the spotlight is truly off the Bucks. The doubters haven’t been this vocal in a long time, with some pundits even predicting Milwaukee to float around the play-in range. Despite the swirling negativity, I don’t think it’ll be that disastrous of a year at all. Pencil me in for a 52-30 year and the number three seed. In addition to this being the year where Milwaukee gets out of the first round, I also think they’ll sneak out a tough series win in the second round. However, I struggle to see them advancing past the Eastern Conference Finals. If I’m picking right now, I’d go with Boston to make it out of the East again.
Van: Boston had an absolute cakewalk to the title last season, and I think when they get a true test next postseason, they’ll find that it ain’t easy to repeat! While I do think they’ll lead the East in regular season wins, I think it will be by more like four or five games as opposed to last year’s fourteen. Given decent health—55+ games for each of Giannis, Middleton, and Lillard—I see the Bucks as a low-to-mid 50s team in terms of wins. I do think they’ll take a lot more pride in the regular season after they underwhelmed with 49 wins last year, which should be enough to rise atop of the second tier of East contenders below the Celtics. I’ll predict the two seed over the Sixers and Knicks, who might have more injury concerns than the Bucks as of today. I’ll take Milwaukee at 54-29 and, at something close to full health, beating Boston in the East Finals. People are very much overlooking how well the Bucks played the Celtics last year. My prediction ends there.
Jack: If the Bucks are locked in and executing at a high level from the start, they will have a chance to get into the mid-50s in wins. On the other hand, their preseason performances—when the main guys have played, at least—have not been overly assuring. Additionally, Khris Middleton won’t be ready for opening night. How long does that linger? So there are undoubtedly many questions surrounding this team. I don’t know… let’s go with 54 wins. As for seeding, I think they will again end up as the three seed, but I could easily see them in second. Ever the optimist, I predicted on Deer Diaries (A Milwaukee Bucks Podcast!) that this team will go to the NBA Finals, and I’m sticking with that—they will dethrone the Celtics.
Riley: I’ve vacillated between optimism, despair, and plain indifference much of the summer (that’s what happens when the most anticipated campaign in a while turns out to be a slog). The core of that disappointing team is unchanged with positive expectations linked to relatively better coaching, improved role players, thoughts about health, and the friendship between Giannis and Dame. Those things aren’t nothing! However, given the age of the roster and the likelihood of nagging injuries popping up here or there, I expect merely the slightest of overall improvements to the record at 50-32. That will give them the three seed, and they’ll make it to the Eastern Conference Finals.
Morgan: Welp. I have the Bucks advancing to the Eastern Conference Semi-Finals. I thought that was optimistic given the last two campaigns, but I guess I’m a Negative Nelly. Ah well. Boston is still Boston, and although I think the Knicks will need time to repair their karma after breaking up the Power of Friendship, I still like their chances over the Bucks. The rest of the East doesn’t scare me (yet), so I’ll keep the Bucks in third at a slightly improved clip of 51-31 and in line for a nervy but ultimately redeeming Bucks in Six first-round win. Looking forward to being proven wrong!
Kyle: I figured there is no reason to be pessimistic, so I will say 51-31, which will be third in the East, but the Bucks will make the NBA Finals.
If the Bucks don’t win it all, it’ll be because:
Gabe: It’ll be because of the same script we’ve seen every year since the title run: injuries. I have faith that a full offseason will help Doc Rivers get this team to where they need to be to put their best foot forward. However, we all know how old this team is. If they get to the end of the regular season and aren’t close to 100% healthy and instead have some injuries that could force star players to miss time, it’s going to be difficult to make up—especially if it’s Giannis again.
Van: It’s probably going to be injuries, but more specifically, something longer-term to one of the big three or anything that keeps Giannis out for multiple games in a playoff round. Of course, there are other potential flaws with the team, but all would be more overcomeable compared to lacking a star during a significant stretch of games. I do think they have much better depth than last year to weather a shorter playoff absence from Middleton or Dame, but only in the earlier rounds versus a less talented team, probably not New York or Philly, and certainly not Boston. Obviously, Milwaukee really needs its big three to take out the East’s other top squads. However, I’m confident in the likes of Taurean Price, Gary Trent Jr., and Delon Wright to not only be better than Jae Crowder, Malik Beasley, and Patrick Beverley but also to give the Bucks high-quality minutes in a series, including if one of the big three is sitting out a game or two.
Jack: They have an imperfect roster that doesn’t lend itself to versatility. At the end of games, Dame, Khris, and Brook will likely be on the floor: three subpar or non-versatile defenders. As we know, injuries could also play a significant role. Finally, I firmly believe Giannis must slightly alter the way he plays to make his teammates better on a more consistent basis if they are to win it all. His usual crash-and-bang style probably won’t work at the highest levels, and diverting from this could prove valuable. Giannis setting screens better and with a higher frequency, committing to playmaking more than scoring, and proactively dictating the game more are what I’ll be watching for throughout the year.
Riley: The defense barely makes its way to league-average or slightly above league-average. I blindly (and stupidly) assumed the once-dominant defense of years ago would be there last season, even after all that personnel churn. My bad on that. Until they show me otherwise over the course of the season, I’ll maintain skepticism on that end and figure it will be the reason they fall short when it matters most.
Morgan: We can’t find a quality five through eight in the playoffs from the five through twelve in the regular season. Milwaukee’s five through twelve are either old, young, or new. We need half of them to pan out against any given playoff opponent, and likely more if injuries beset the aging top four. I’m excited for the regular season because it will give us a chance to see if the oldies are washed, the youngsters are ready, and the newbs will fit in. There are a lot of options here, but what the Bucks really need is a few quality options. They haven’t had those since the title run.
Kyle: I’ll take a different approach than everyone else, but I will say the offense stagnates/goes cold. There could be issues like Giannis struggling at the free-throw line or Dame and Khris having very inefficient shooting nights. It could be similar to the 2022 series against Boston where all the role players simply can’t hit a shot.
If the Bucks do win it all, it’ll be because:
Gabe: The vision that the Bucks had of Damian Lillard and Giannis Antetokounmpo comes to fruition. Last season, there were endless thoughts of how the duo would pair up. Ultimately, it was a rollercoaster of a campaign that featured three coaches, frequent lineup changes, and zero minutes of Giannis and Dame playing with one another in the playoffs. You also had the limited amount of time where Giannis, Dame, and Khris saw action together. I anticipate Giannis to produce like he normally does, but I’m eager to see what Lillard can produce. He’s been so transparent with how different this offseason has been for him, beginning with workouts and training. That whole routine of his was messed with last year since Portland was actively shopping him. This year, he had a full offseason to gel with his teammates and coach. Barring any injury to him, I anticipate him having a bounce-back campaign.
Van: They stay healthy enough and they actually are as good as they look on paper. While you can still identify weaknesses defensively on the wing and in the backcourt, then perhaps in terms of ballhandling, I think there’s enough on the roster today to be one of the league’s elite teams with a high-octane offense and a solid defense. More specifically, it will be because their corps of wings manage to keep Jayson Tatum and Jaylen Brown just enough in check during the East Finals.
Jack: They win on the margins. Bobby and Dame are five to ten percent better on defence; Gary Trent Jr., Taurean Prince, and Delon Wright prove substantial upgrades over their predecessors; Giannis plays more as a hub; the big three stay healthy, etc.
Riley: Doc Rivers has convinced Dame and Giannis to spam pick and rolls a million times during the regular season. That play type won’t win a title on its own, but it should be one of many tools the team uses to improve that relationship from functional (and thus good because of how talented they are) to deadly. If this team wins it all it will be thanks to that duo in particular living up to their innate potential.
Morgan: With respect to Tolstoy, a happy family—in this case, the Bucks—is actually just the reverse of an unhappy family. Give me a quality five through eight, and I give you a championship.
Kyle: The bench provides positive contributions. The Bucks won the title because of one or two bench players stepping up and executing. Milwaukee will need that same approach as well from Bobby, Prince, Delon, and whichever AJ/AJJ goes out there.
Where will Giannis finish in MVP voting?
Gabe: There’s so much talent in this league. You can legitimately make the case for five or six players. It’s honestly wide open. Ultimately, I think Luka Doncic will take home his first MVP trophy. I’ll go with Nikola Jokic finishing second, and then Giannis coming in third.
Van: It seemed preordained that Doncic would be the 2025 MVP even before the Mavs made the NBA Finals. I think that will be the way voters go because many have just been itching to crown him for a while, given how often he’s been people’s preseason MVP pick in recent years. I do think Giannis will finish top-three, though (it’s a joke that he didn’t last season after being the first player in league history to average 30 a game on over 60% shooting), but I’ll guess Shai Gilgeous-Alexander is the runner up again. As we saw with how Giannis’ MVP candidacy ebbed after winning it twice, then winning a title but lacking playoff success since, the three-time MVP Jokic’s time as a finalist is likely done until Denver makes another deep run.
Jack: Gosh, you tell me! It feels like “The Media” has really soured on the Bucks in recent years, and that has extended to Giannis. Antetokounmpo does have the advantage of having not won it for a while, so voter fatigue may not be such an issue. But it also feels like pundits might want to give it to Shai Gilgeous-Alexander or Luka Dončić. I don’t have much hope in this department. I’ll say fourth.
Riley: Third or fourth, probably. I think he will put up stat lines which will demand some attention, but any relatively “pedestrian” performance by the Bucks in terms of wins and losses will automatically limit his ceiling. Being the best player in the Eastern Conference matters. Competing against Western Conference guys who will either put up even gaudier stats and/or be part of a more successful overall unit and/or benefit from “narrative arcs” (see: Anthony Edwards taking a leap and people jumping aboard that shark) shall likely be too much for Giannis to overcome. Either way, it doesn’t matter. The playoffs are all that counts for Giannis this year.
Morgan: The WNBA finals really accelerated my personal journey along the general trend that people are more likely to fall prey to conspiracy theories as they age. “They” decided that the Liberty would win, and “they” will decide that Luke will win the MVP.
Kyle: I’m guessing fifth. Jokic will still be the media darling but I don’t think they want to give him another one. Anthony Edwards, Shai Gilgeous-Alexander and Jayson Tatum will be higher. Luka Doncic seems to be the pre-written winner that the media wants.
The Buck that will take the biggest step forward will be:
Gabe: Give me AJ Green. He may be taking a bit of a back seat with all the offseason change that Jon Horst brought upon to this team, but I think there’ll still be plenty of opportunities for him to shine. Injuries always happen, and it wouldn’t surprise me if that opens the door for him. Doc has always been an advocate of his and we all know how he can shoot the ball. If he’s able to prove that he can continue to bolster his defense, that’ll only make him that much better. It may be tough at the beginning of the year for Green to make a case, but if he brings consistency throughout the year, I could see him playing meaningful minutes come the postseason.
Van: He isn’t one of the young guys, but Pat Connaughton had a very good preseason in terms of shooting and looked a bit more like his old self physically. I could see this portending a bounce-back year, and it looks like he’ll be in the rotation to start the season. If I’m way off here and Connaughton is still on the downswing we’ve seen the past two years, I think it’s most likely to be Green, though he shot the three pretty poorly this preseason. That wouldn’t concern me if he shot better than 18% from deep in the Indiana series.
Jack: Although his preseason has been underwhelming, I’ll go with AJ “Dairy Bird” Green. He’s the most likely of the young guys to be trusted by Doc Rivers, and that trust should give him extra confidence to play his game. He has more upside as a movement shooter, and I’m excited to see what ATOs (after timeouts) Doc draws up for Green.
Riley: Damian Lillard. A second season will mean even higher expectations as all the issues that plagued his inaugural campaign are (hopefully) settled. I’m putting a lot of chips on his sorting things out and giving far more flashes of the player people were so excited about 365 days ago. For a player of his talents even a modest “step forward” would translate to substantial gains on the court.
Morgan: Chris Livingston? I’m not sure he advanced past go last year, which gives him the most room for improvement. He actually looked like a basketball player in Summer League, so maybe that portends some decent, non-garbage time minutes for him this season. Doc is the question mark here, but when the old folks ahead of Livingston start dropping like flies, and he offers a more reliable, if unexciting, option than the other kiddos, he should get the nod.
Kyle: AJ Johnson could go from extremely raw to promising through the season. I’m not expecting him to be in the playoff rotation by the end of the season, but him ending the season with fans knowing he could be the backup point guard next year will be a big step in his development.
The Buck that will regress the most will be:
Gabe: I don’t think Bucks fans are going to like this answer and I could very easily be wrong, but I’m going to say Brook Lopez. I don’t think he’ll regress to a point where he necessarily has a bad season, but I could see him playing to the point where you at least begin to see the cracks starting to develop. Once the playoffs roll around, he’ll be 37 years old. We all know Father Time is looming, but Brook is doing whatever he can to postpone him. Now, what will that exactly look like? I’d anticipate it to show more from a defensive standpoint where he may not be able to bring the rim protection like he’s done in years past. Maybe he will miss more games. However, it wouldn’t surprise me if this is the year where his play starts to trend a little south.
Van: You could easily make a case for Connaughton or Lopez here, but I went with Connaughton above, and I still think Lopez is going to defend at a pretty high level since he relies much more on size and smarts than athleticism. I’m also pretty bullish on the three minimum additions, so I’m going to make the case for Bobby Portis. While his production will probably look similar to recent years in terms of regular season averages and will be enough for him to opt out next summer, his postseasons have mostly been bad in Milwaukee. It just seems like the lights get too big for him: his playoff FG% is 3.3% lower, and his 3P% is 9.3% lower as compared to his regular season averages as a Buck. Unless the Bucks are often dealing with frontcourt injuries in the playoffs, I think he’ll be surpassed in the rotation by the more postseason-proven and defensively-sound Wright and Prince.
Jack: I could see the Brook Lopez angle, but I’ll go with Pat Connaughton. Connaughton had quite an impressive preseason, so let’s hope this doesn’t happen. But statistically speaking, Pat has been on a steady decline the past few years, and the elements of his game that made him unique have been wearing off. If Connaughton can’t provide bankable contributions most nights (shooting, defence, playmaking), he risks losing his spot in the rotation.
Riley: I will have to zag to my colleagues Connaughton zig if only because you have to believe there’s anything to regress from to vote for him. Instead, I’ll go with Andre Jackson Jr.—NOT due to an unbelievably great rookie season, but because he showed enough to get us thinking there’s more there. Early (exhibition) returns suggest it could be rockier than anyone would prefer, and there’s a good chance we end this season with another batch of question marks about another young guy whose theoretical developmental arc was important to the team’s medium-term future.
Morgan: Regression is a strong word. I don’t expect much improvement from folks besides the youngins, but I don’t expect much more than slight regression either. Unfortunately, the person that fits this question best to me is MarJon Beauchamp. Although he doesn’t have much room to regress (a la how Livingston has a lot of room to grow), from a proportion standpoint, if he ends up permanently benched and out of the league after this season—not a huge if—that’s quite the regression.
Kyle: I could see Bobby Portis having a down offensive year. Father Time and Lethal Shooter regression are undefeated.
Offensive/Defensive League Ranking:
Gabe: The days of Adrian Griffin leading this defense are gone. Doc Rivers was able to make an immediate impact on defense once he arrived and I believe he’ll deliver top-ten status this season. Give me six for defense. I think the offense will keep producing at an elite rate as well, especially if everyone remains healthy. Give me a number five ranking for that end of the floor.
Van: Doc knows how to actually coach defense whereas Griffin probably does not. The addition of assistant Greg Buckner to the bench might be the sneaky best coaching move any team made this year; he was an architect behind Cleveland’s top defense the past few seasons, one that featured a huge rim-protecting center, a hyper-athletic and lengthy four man, only one legit wing defender, then two small guards who aren’t known for playing good defense. Sound like another pro basketball team on a Great Lake? I’ll be pleasantly surprised if Milwaukee finishes inside the top ten, but they’re good enough to finish solidly above league average, so I’ll say eleven. Much was made about the offense’s decline under Rivers, but much of that came while Middleton was nursing his ankle sprain, and then the big three only got six games together when he returned. Six! This is much more likely to be a top-ten unit, and after finishing sixth last year, I’ll put them at fifth as other offenses (namely Phoenix and New York) also improve.
Jack: Milwaukee finished sixth last year in offensive rating, and I think that will stay mostly steady. If they want to get into the top three, I think Giannis will need to play a Jokić-like role as a short-roll playmaker, averaging nearly ten assists per game. As for the defence, Milwaukee finished nineteenth last season. That must improve significantly. We know Doc cleaned up a lot of low-hanging fruit relating to transition and pick-and-roll defence. How much can better defensive personnel do to boost that improvement this season? I’ll say that I think this team can get up to eighth, but I’d probably settle on tenth.
Riley: I’ll be optimistic and say fifth in offense and sixteenth in defense. Van’s points about the coaching staff and personnel upgrades are completely valid and a point for optimism. I will not pretend to be an elite Darius Garland mind—he could be and may be worse than Dame, I’m sure—but the age factor impacts more than Dame. The composition of the entire playable veteran rotation will have me limit my expectations.
Morgan: Let me get out my abacus. Slight rebalance of offense vs. defense plus slight improvement across the board nets me fifth in offense and sixteenth in defense. Which is unfortunately what Riley said, but ah well. Color me floored that they finished sixth in offense last year, so at least a slight upgrade seems right. As far as finishing nineteenth in defense… room for improvement.
Kyle: I have no idea how this will play out, but let’s say ninth in offense and thirteenth in defense.
Who fills the Thanasis role on the bench as the team hype man?
Gabe: First, let me say this. Nobody will fill Thanasis’ shoes on the bench—and I guarantee you’ll get the same answer from everybody on the team. However, if I were to choose, I’d go with Andre Jackson Jr. He’s obviously not as goofy as Thanasis, but I can see him bringing his good vibes to his teammates and getting in some prime three-point celebrations during clutch playoff moments. The dark horses are one of the rookies.
Van: If they manage to trade MarJon Beauchamp anytime soon and open a roster spot as rumored, it’s going to be Thanasis himself, as long as his Achilles is healthy enough to stand up. If they can’t open a roster spot for him between now and season’s end or they go a different route, I think AJ Johnson is just goofy enough in that D.J. Wilson sort of way to be the hype guy.
Jack: Give me Andre Jackson Jr. I don’t think anyone can out-Thanasis Thanasis, but I love how Jackson goes about it and how much he wants to contribute to winning.
Riley: Liam Robbins is blessed to be here and already beat out one teammate for a very niche and specific role. Who is to say he can’t follow that up with the kind of cheering that has us wondering whether he may be, in fact, the legendary sixth Antetokounmpo brother?
Morgan: Pat Connaughton, easy. He’ll likely be on the bench more this season, he can jump high to convey excitement, and he needs this job in order to keep an eye on his real-estate empire. He’ll do whatever it takes to be a Buck for Life.
Kyle: Chris Livingston feels like the guy who could fill the role.
How many times this season does Doc Rivers start an answer to a question with “you know” in his postgame pressers?
Gabe: Let me try some rough math here. Okay, so there are 82 regular-season games. In the first round, let’s say Milwaukee advances in five games. In the second round, let’s have that series go seven. I have the Bucks getting knocked out in the Eastern Conference Finals. Let’s say that goes six games. That’s an additional eighteen games, resulting in a total of 100 games. Doc will typically get asked about ten or so questions a game, give or take a few. Out of those questions, I can see him saying “you know” in about half of them. But then the playoffs will feature more questions. So, out of 1,000 questions that’d initially come from 100 games, let’s tack on 250 more questions for the big games. I’ll predict he says “you know” about 625 times throughout the year. And no, I won’t be counting.
Van: As many times as Giannis says “at the end of the day” or Bud started answers with “yeah, no.”
Jack: What Gabe said, LOL.
Riley: The limiting factor to this is the parameter that Gabe threw on there. If we’re only counting postgame pressers, the cap on this goes way down. That means we miss out on mid-week availability, pre-game chats, and every interview he gives to Balkan-based basketblogs with five readers (his personal favorite subset of media). I’ll Price Is Right Gabe here and say 624. Godspeed to our beat writers.
Morgan: You know, someone should count. If so, expect a thorough and ultimately pointless analysis from yours truly about whether Doc employs “you know” more against big market opponents as a subtle dig at slanted media bias.
Kyle: I have no idea, but it will be a fun Brew Hoop piece to work on during the All-Star Break (editor’s note: is Kyle volunteering to track them? Is he insane?).
This year’s fan favorite will be:
Gabe: Some fans may not be able to stand him anymore, but it’s going to be Bobby Portis until he leaves Milwaukee.
Van: I think (hope) that since the Bucks will take the regular season more seriously this year, they’ll blow some teams out. Perhaps not as often as those 2018–20 teams, but barring a Thanasis return, someone will be the victory cigar who enters when the game is out of reach, thus becoming a fan favorite for that sole purpose. Teams can only dress twelve or thirteen players per night, and if the rest of the roster is healthy, I think Johnson is usually going to be that final guy over Tyler Smith or Chris Livingston. Add in the fact that he’s a first-round pick who everyone wants to see succeed, and he’ll get a warm ovation when he gets up off the bench to check in during a rout.
Jack: Liam Robbins. The haircut alone will make him a cult hero.
Riley: Pat Connaughton will have no fewer than five instances during the course of 41 home regular games where he has A Moment that gets the crowd going. In a season with role guys here to cash checks for a season before moving on to greener salary pastures and opportunities to hate-watch Bobby Portis, Pat will have enough moxie to convince us he’s still got whatever “It” is.
Morgan: Trent seems like just the sort of “hate to play him, love to have him” guy that Milwaukee loves. But count me in for Dame (if he’s not too good to be eligible) as he elevates his game and the Fiserv faithful do due diligence to make him feel at home after a rocky first year.
Kyle: AJ Johnson, being a full-on Gen Z, will work with a contingent of Bucks fans. Plus, we all want him to be good.
We’re also curious to hear all of your predictions as well! Feel more than welcome to chime in with your thoughts in the comments.
Milwaukee, WI
13 Things to Do in Milwaukee This Weekend: July 9-12
Featured Events
1. Bastille Days
ALL WEEKEND AT VARIOUS TIMES | CATHEDRAL SQUARE PARK
Milwaukee’s French-themed festival is coming to Cathedral Square Park this weekend. The festival will feature French and Cajun cuisine, live entertainment, a 43-foot Eiffel Tower replica and more. The Storm the Bastille 5K run/walk is Milwaukee’s only nighttime 5K, kicking off the festival at 9 p.m. on Thursday. Entrance to Bastille Days is free all weekend.
2. Festa Italiana
FRIDAY, SATURDAY AND SUNDAY AT VARIOUS TIMES | HENRY MAIER FESTIVAL PARK
Festa Italiana is serving up authentic Italian eats, live music, cultural performances and more this weekend. Don’t miss out on the Milwaukee’s Best Sauce contest! General admission is $18 and tickets can be purchased online in advance.
3. Whitefish Bay Art Fest
SATURDAY AND SUNDAY FROM 10 A.M. TO 5 P.M. | EAST SILVER SPRING DRIVE
Check out 100 original artists making their way to Whitefish Bay for their annual art fest. Artists will be selling everything from jewelry to photography alongside cold beer and good food. A Kids Art Zone will be hosting art projects and face painting and live art demos allow guests to get to know the artist’s process. Entrance to this event is free, but you can reserve up to two tickets for complimentary food, drinks and desserts.
Experience an unforgettable evening celebrating great design!
More Events
4. Wait Wait… Don’t Tell Me!
THURSDAY FROM 7:30 P.M. TO 9:30 P.M. | RIVERSIDE THEATER
Peabody Award-winning comedy news quiz show Wait Wait… Don’t Tell Me! Is coming to the Riverside Theater. Hosted by Peter Sagal, a rotating panel of comedians, writers and celebrities review the week’s news before contestants are quizzed for the chance to win a custom-recorded greeting by a cast member for their voicemail. Tickets start at are $35 each and can be purchased online.
5. PRO’S 20TH Anniversary Party
FRIDAY FROM 6 P.M. TO 10 P.M. | THIRD SPACE BREWING
Performance Running Outfitters is celebrating 20 years serving the running community in Milwaukee. The celebration takes place at Third Space Brewing and will feature interactive activations from many of the top running gear brands. The party will also include local food trucks, live music and craft beer.
6. Sip and Strut 2026
FRIDAY AT 6 P.M. | CORK WINE AND COCKTAIL BAR
KenVogue LLC is transforming Cork Wine Bar into a Paris-inspired runway featuring local brands, designers and models. The night combines fashion and elegance with local pride and creativity. General admission tickets are $30 each and VIP tickets include an exclusive gift bag and dinner provided by Sydney Serving.
7. Starry Nights: Rockin’ Robins and Classic Car Show
FRIDAY FROM 6:30 P.M. TO 8:30 P.M. | GERLACH/HAACK OUTDOOR THEATER
Jam out to music from the 50’s and 60’s with the Rockin’ Robins while celebrating National Collector Appreciation Day with the Wilson Center Classic Vehicle Show. This joint event is a part of the Starry Nights concert series and both are free to attend. If you plan to stay for the music, make sure to bring chairs or a picnic blanket.
8. Wine Glass Painting Workshop
FRIDAY FROM 6:30 P.M. TO 9:00 P.M. | A STROKE OF GENIUS PAINT WINE STUDIO
Join the staff at A Stroke of Genius Paint and Sip for a fun and relaxing wine glass painting workshop. The team will lead lessons on simple painting techniques including brush strokes, patterns and decorative techniques. A ticket to the class includes the lesson, practice exercises, two wine glasses to paint, all painting supplies and access to the full bar. Tickets are $305 each and can be purchased online.
9. The Fine Arts Quartet 80th Anniversary Series
FRIDAY FROM 7:30 P.M. TO 9 P.M. | ZELAZO CENTER FOR THE PERFORMING ARTS
The Fine Arts Quartet will celebrate 80 years with a free concert featuring Brahms Piano Quartet #3. The program features Gisele Witkowski and Fabio Witkowski as guest pianists. No ticket is required to attend this show.
10. 2026 Dragon Boat Festival
SATURDAY FROM 8 A.M. TO 4 P.M. | SOUTH GATE PLAZA
Spend Saturday on the shores of Lake Michigan and celebrate the spirit of teamwork, cultural heritage and more at the Dragon Boat Festival. Dragon boating teams from across the region will compete in multiple divisions throughout the day while family-friendly activities, traditional performances and authentic cuisine offer an immersive experience on land. Entrance to the festival is $5 per person over the age of 13.
11. Time Travelers Vintage Expo
SATURDAY FROM 10 A.M. TO 5 P.M. | BAIRD CENTER
Travel back in time at the Time Travelers Vintage Expo and enter a retro wonderland. The expo brings together small businesses, curators and artists from across the US to offer the best vintage clothing, home goods, retro-inspired handmade items and more. Sellers offer a wide range of styles and price points, so there’s something for everyone. Tickets to the expo are $11 each and can be purchased online.
12. The Allis Fiber Festival
SATURDAY FROM 12 P.M. TO 4 P.M. | CHARLES ALLIS ART MUSEUM
Explore the many rooms of the Allis mansion and discover the world of fiber arts. Each room will include a different fiber or textile practice and include live demonstrations. In the courtyard, guests can meet fiber-bearing animals including llamas, alpacas and rabbits. Participation in this event is included with museum admission and free for members.
13. Bop to the Top
SATURDAY AT 9 P.M. | THE RAVE
Calling all Disney Channel girlies, it’s the Bop to the Top Tour! In honor of 20 years of Hannah Montana and High School Musical, this dance party will feature all the hits from Hannah Montana, High School Musical, Camp Rock, Lemonade Mouth and more. Full audience participation is expected, including screaming all of the lyrics. This event is 18+ and general admission tickets start at $28.
Milwaukee, WI
Opinion: Milwaukee teachers have more to give. Let’s give them the chance. | Milwaukee Neighborhood News Service
Milwaukee, WI
College wasn’t on his radar. This nonprofit helped him — and hundreds more
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Maximus Bryant is a self-described gearhead, but he never knew what he wanted to do with his knack for cars and handiwork.
In the back of his mind, though, was his teacher’s voice nudging him to consider college. Ross Romenesko, a former Milwaukee Public Schools teacher, recognized Bryant’s interests and pushed him toward engineering.
Bryant graduated from the Milwaukee School of Engineering in 2025 and works for Harley-Davidson. Without Romenesko, he said he probably wouldn’t have even studied electrical engineering.
Hundreds of other Milwaukee students have also seen their life trajectories shift thanks to encouragement from Romenesko and Future Urban Leaders, the nonprofit organization he co-founded in 2015. Bryant was in the first class of 13 students.
The nonprofit’s tight-knit support system and STEM-based activities helped Bryant learn his interests and find the right pathway for him after high school.
“[Future Urban Leaders] is not just an organization, [it’s] a family,” Bryant said. “[Future Urban Leaders] is about improving you as an individual first.”
The nonprofit celebrated its 10-year anniversary in 2025, and staff has been reflecting on ways to expand and continue serving Milwaukee’s youth.
Future Urban Leaders serves K4 through high school students in Milwaukee
Founded by Romenesko and local business executive Brandon Vonck, the nonprofit serves young people in Milwaukee from ages 4 to 18.
Grade K4-8 students at Milwaukee College Prep Lloyd Street Campus can participate in the nonprofit’s programming. They focus on personal, emotional and creative skills.
“[We] start that early because you’re tapping into a young mind that’s very impressionable, very moldable,” said Darnell Hamilton, the nonprofit’s executive director.
High school programming is open to students citywide. They learn leadership skills and explore post-secondary and career opportunities.
“They gave us the resources to be able to expand ourselves,” said Trinitee Turner, a Future Urban Leaders alumna and incoming sophomore at the University of Wisconsin-Madison.
The ultimate goal is to mold students as people and provide tools and opportunities for students to ultimately find a path in college, trades or otherwise.
“It’s our job … that before you walk across the stage that we’ve done our part in this village mindset … to be a part of you figuring out what the next destination of your pathway is,” Hamilton said.
The program requires students to apply, though every eligible student has been accepted to date. The nonprofit serves about 150 students annually.
It’s been more than 10 years. Is the program successful?
To understand the past decade of program effectiveness, staff surveyed parents and students.
About 85% of parents said the nonprofit supported their children’s leadership skills, 90% of parents were satisfied with program quality and 90% of parents were pleased with staff engagement in the development of their children.
The nonprofit also monitors student retention, academic success, high school graduation and post-secondary plans. Staff keep in touch with students even after they graduate.
During the school year, staff meet regularly with students to hear how they are doing in school, take them on college and workplace visits, prepare for events and interviews, play golf and more.
What will the future of the program look like?
Hamilton hopes to help larger classes of students in the future if staffing can also increase.
The nonprofit currently has three part-time and three full-time employees on staff.
Hamilton also hopes to improve marketing and make more people aware of the organization.
Future Urban Leaders forms lifelong connections
Students can be in the program for up to 14 years but some alumni choose to stay connected even beyond that.
Bryant said staff are still invested in his day-to-day life, including some he now calls his friends. He helped Romenesko set up a play set for his daughters in his backyard in June.
Turner feels the same way. Her younger sister is now enrolled in the program. When Turner picks her up, she can’t help but stay and chat with staff that helped her during her own time in the program.
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