As Bucks welcome Damian Lillard to Milwaukee, questions remain about the roster

MILWAUKEE — Thirty minutes after Damian Lillard landed in Milwaukee on Saturday, the Bucks’ new starting point guard pulled up in front of Fiserv Forum in a black SUV with his family. An estimated 5,000 fans waited in front of the arena to welcome their city’s newest star, and the crowd got its chance as a security guard opened up the rear passenger side door for Lillard.

“Hey, Milwaukee, what time is it?” bellowed a voice over the sound system set up for the event in the plaza outside of the arena.

“Dame Time!” the fans yelled in response.

After another round of the same call and response, Lillard helped his three children out of the car and then shook hands with Bucks president Peter Feigin, Milwaukee County Executive David Crowley and the Mayor of Milwaukee Cavalier Johnson before making his way toward the arena on the path cleared for him through the crowd. With his son, Damian Jr., leading the way and his twins, Kalii and Kali, in his arms, Lillard made his way toward Fiserv Forum as the crowd roared and a group of Bucks front-office personnel — including Bucks general manager Jon Horst — piled out of the cavalcade of black SUVs and followed Lillard into the arena.

While Horst and his front-office staff worked throughout the last week to deliver Lillard to Milwaukee, this trip from the airport, even if ceremonious, actually brought Lillard to his new home arena. Lillard did not speak to reporters on Saturday, instead waiting to make public comments on Monday at media day, but he did check out his new threads in the Bucks’ locker room.

With Lillard now in Milwaukee, the Bucks have their guy in house, and they can get ready for the 2023-24 season. Still, there are questions about the roster outside of Lillard. Let’s take a closer look at them.


How Damian Lillard transforms the geometry and gravity of Milwaukee’s offense

What about the starting shooting guard spot?

While much of the attention regarding what the Bucks gave up in the trade has understandably been given to Jrue Holiday, they also gave up their starting shooting guard for the last two seasons, Grayson Allen. While his play was heavily critiqued, Allen appeared in 138 of the Bucks’ 164 regular-season games and played the fourth-most minutes of any Bucks player across the last two seasons.

Figuring out how to replace Allen’s spot will be a tough decision for Bucks coach Adrian Griffin. There is no shortage of candidates, and the gravity created by having both Giannis Antetokounmpo and Lillard in the lineup allows those candidates to bring something useful to the table.

A quick look at the options, in alphabetical order:

  • Malik Beasley: If the Bucks want to fully commit to becoming one of the league’s most high-powered offenses, Beasley could be the choice. Since 2016-17, among players who have appeared in at least 100 games, the 26-year-old shooting guard is 10th in the NBA in 3-point attempt rate with 9.5 attempts per 36 minutes. Every player on the floor in a Bucks starting lineup featuring Beasley would present problems for opposing defenses.
  • MarJon Beauchamp: The Bucks’ second-year wing is unproven, but he could be the most versatile defensive option. At 6-foot-6 with a 7-foot wingspan, Beauchamp offers serious length. He spent most of last season covering point guards and shooting guards, which would fit well with Lillard because it would keep him off the opponent’s top option defensively.
  • Pat Connaughton: No one has played more minutes with the other four starters than Connaughton, and that includes Lillard because they were teammates in Portland for the first three years of Connaughton’s career. The Bucks’ 30-year-old wing is a floor spacer, competes defensively and doesn’t need a ton of shots to be happy — which could be useful considering there may not be many shots to go around.
  • Jae Crowder: Things did not go how the Bucks were hoping when they added Crowder at the trade deadline last season, but Crowder is less than two years removed from being a starter on the team with the NBA’s best record in Phoenix. At 6-foot-7, he would add quite a bit of size to the starting lineup, and the offensive prowess of the rest of the unit would allow him to focus on the defensive end.

Griffin will need to think through not only what each of those players could bring to the starting lineup, but also how they might be useful coming off the bench and the potential pairings they could create staggered with one of the Bucks’ superstars later in the game.

What about the luxury-tax implications?

This will be the Bucks’ fourth consecutive season paying the luxury tax. They would have narrowly avoided it during the 2020-21 season, but Holiday’s (unlikely) championship bonus pushed them into the luxury tax for the first time, and they have been there ever since as the Bucks’ ownership group has continued to approve Horst’s pursuit of a championship-level roster.

Before the Bucks traded Holiday, they were going to go into this season with $181,781,585 on their cap sheet with the contracts of the 15 players on the roster. That total was going to be well over the salary cap of $136,021,000 and the luxury-tax threshold of $165,294,000, as well as the first luxury-tax apron at $172,294,000.

And while the Bucks’ salaries that count against the cap would end up below the second luxury-tax apron at $182,794,000, the unlikely bonuses in the contracts of Holiday and Khris Middleton would have pushed them over the second apron because that is calculated differently than the salary-cap figure, as we learned from John Hollinger in mid-July.

With roughly $181.78 million in salaries, the Bucks were going to have to make a luxury-tax payment of about $49.77 million after the season if they kept their roster the exact same as it was before the trade for Lillard and none of the team’s contract bonuses hit.

If the Bucks choose to keep only 14 players on the roster, they will have cut their salary total (and luxury-tax payment) slightly from the total before the trade. But if the Bucks choose to fill the final spot on their 15-man roster with a veteran minimum contract ($2.02 million), they will add $8.58 million to their luxury-tax payment because of the rules associated with the league’s repeater penalties.

For this season, increasing the team’s salary total and jumping further above the second apron doesn’t come with real punitive consequences. Any real difficulties with the luxury tax stemming from the acquisition of Lillard will take place next season.

Teams above the second apron next season will not be able to use the taxpayer midlevel exception, aggregate trade exceptions to reach a greater salary, convey cash in a trade (so no buying second-round picks) or complete a sign-and-trade. On top of that, if the Bucks are above the second apron next season, their first-round pick in the draft following the last day of that salary-cap year will be frozen, which would mean the Bucks could not trade their 2032 first-round pick.

With Lillard on the books instead of Holiday, the salary base for the core of the team jumped up nearly $12 million, which will make filling out the bottom of the roster and avoiding the second apron far more difficult. The core four players — Antetokounmpo ($48.79 million), Lillard ($48.79 million), Middleton ($32.97 million) and Brook Lopez ($23 million) — will be paid $153.55 million next season. Even with a salary-cap increase, those four players alone will take up the Bucks’ entire salary cap. Add in roughly $22 million for Connaughton and Bobby Portis, and the Bucks have more than $175 million in salary committed to just six players.

Initial salary-cap projections for next season based on league guidance put the luxury-tax line at $172.5 million, which would mean the second apron will end up being approximately $190 million. From there, it would not be impossible for the Bucks to sneak under the second apron, but it would be incredibly tight, especially considering that unlikely bonuses count toward that second apron figure.



How Damian Lillard transforms the geometry and gravity of Milwaukee’s offense

What about the long-term future?

Being concerned about the Bucks’ future because of the subsequent picks and pick swaps thrown into the trade is logical. It is pretty ugly down the line.

At the moment, the Bucks cannot trade the rights to any first-round pick. The next first-round pick they control is their 2031 first-rounder, and league rules dictate that they cannot trade that pick until after the 2024 NBA Draft.

  • In 2024 and 2026, they will give the Pelicans the right to swap for the better of the two teams’ first-round picks.
  • In 2025 and 2027, the Bucks are sending their first-round pick to the Pelicans.
  • In 2028 and 2030, the Bucks will give the Trail Blazers the right to swap for the better of the two teams’ first-round picks.
  • In 2029, the Bucks are sending their first-round pick to the Blazers.

At the start of the 2030-31 season, Lillard will be 40 years old, and Antetokounmpo will be weeks away from turning 36. Middleton will be 39, and Lopez will be 42. There is a decent chance the three players not named Giannis will be retired by that point, and any of those four players would have needed to sign multiple contract extensions to still be with the Bucks by the time that season comes around.

In short, that is a long way off, and it’s a long time to go without controlling a first-round pick. But this trade was not done as part of a 10-year plan or even a five-year plan; it was done to capitalize on having one of the best players in the world in Milwaukee and building a team around him that can compete for a championship over the next few seasons.

If the Bucks eventually need to tear this roster apart and attempt to recoup some of those assets, they will likely get a chance to do that, but they will likely never recover every future piece they have sent away. In the end, winning the franchise’s second NBA championship in 2021 made mortgaging future picks for Holiday worthwhile. The same would be true of another championship during Lillard’s time with the Bucks.

(Photo of Damian Lillard: Patrick McDermott / Getty Images)

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