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Bucks offseason primer: Giannis Antetokounmpo, Khris Middleton, cap casualties, more

The 2023 Milwaukee Bucks may go down as one of the greatest teams in modern history to be eliminated in the first round as their season came to a shocking end to the No. 8 seed Heat in five games. A back injury to Giannis Antetokounmpo gave Miami an opening to steal two games and the Bucks couldn’t recover from it. They now head into the summer with the burden of wasting a season from their title window.

The Bucks were already heading toward an inflection point with the cost of keeping the core together set to rise significantly. Ownership has already gone deep into the tax for this team, but it’s unclear where exactly they might draw the line. Could there be cap casualties earlier than expected after getting eliminated from the playoffs prematurely?

Here is a preview of the 2023 offseason for the Milwaukee Bucks.

State of the roster and potential luxury tax projection

Mike De Sisti, Milwaukee Journal Sentinel

Milwaukee is heading into the offseason with eight players under contract and just $4.1 million below the projected $162 million luxury tax line. This projection includes Khris Middleton and Jevon Carter picking up their respective player options. If both players opt out and walk, the Bucks still would project to operate over the cap. This makes retaining all of their most valuable free agents a priority this summer.

Milwaukee also projects to be $16.4 million below the projected second apron but are expected to go over it once they fill up their roster. Doing so will eliminate access to their taxpayer mid-level exception and limit their return in trades to 110 percent of their outgoing salaries. The only other ways they can increase their payroll is by re-signing their own free agents, signing minimum players, and signing the 60th overall selection in this year’s draft.

Ownership went deep into the tax this season paying a franchise record $83 million in penalties. Because they were taxpayers for three straight seasons, they are set to enter the repeater tax for 2023-24. This would increase each tax level by an additional dollar, which would significantly increase their penalty even if they have a similar payroll. If they were in the repeater tax in 2022-23, their tax payment would’ve cost an additional $30 million.

How deep ownership is willing to go into the repeater tax remains to be seen. They are going to need to re-sign several key free agents if they’re going to have a shot to compete again next season. Re-signing Brook Lopez, Joe Ingles, and Jae Crowder, while signing two minimum players and their second-round pick to a minimum salary could give the Bucks a tax payment in the $125 million range. This would put their payroll and tax combination just north of $315 million.

How the new CBA affects them

The Bucks essentially have to choose between paying historically high tax penalties while being restricted toward improving the roster to compete for championships, or blowing the team up. The choice seems obvious now while they have Antetokounmpo in his prime but the new CBA changes may cut Milwaukee’s window shorter than expected.

Assuming the Bucks are willing to be repeat taxpayers it’s reasonable to expect to see this group together for another two years. Not only could Antetokounmpo and Holiday’s contracts alight to end in 2025, but that is also the last year before luxury tax rates rise. All repeater tax levels will rise substantially starting in the 2025-26 season. The amount the Bucks were over the tax in 2022-23 would equate to a $75 million higher payment in 2025-26.

Another restriction the Bucks will have by being over the second apron starting in 2023-24 includes not being able to sign players waived mid-season whose salaries were for more than the non-taxpayer mid-level exception. Starting in 2024-25, they wouldn’t be able to take on more than 100 percent of outgoing salaries in trades, aggregate players in trades, convey cash in trades, use trade exceptions from the previous season, or sign and trade a free agent in exchange for players under contract or a trade exception. These restrictions effectively stick the Bucks to their core with significant changes only coming by trading their highest-paid players for smaller contracts.

Finishing over the second apron in 2023-24 would also freeze them from trading their first-round pick seven years away. And if they finish 2024-25 as a second apron team again, that pick would be dropped to the end of the first round. The roster-building limitations and future draft consequences would be very disadvantageous to the Bucks who already are out on three first-round picks over the next seven drafts. Draft picks are now more valuable in the new CBA since they are one of the few ways for teams over the second apron to add depth.

Potential free agent or extension-candidate: Khris Middleton

Petre Thomas-USA TODAY Sports

Khris Middleton has a $40.4 million player option but he could be looking at a new contract whether he picks it up or not. If he declines it, he would be able to re-sign with the Bucks for up to five years, projected at $272 million. Another team with cap space would be able to sign him for up to a maximum of four years, projected at $201.7 million. Teams with cap space looking to make a run toward the playoffs like the Rockets, Pistons, and Magic could all make a lucrative offer for him.

If he picks up his option, he will be eligible to extend for up to four years, $220.6 million. He could also avoid free agency by declining his option and extending with the Bucks by June 30 for up to four years, $204 million. The Bucks wouldn’t be able to replace him if he leaves, so retaining him in free agency or through an extension will be a top priority this summer.

Free agent: Brook Lopez

Petre Thomas-USA TODAY Sports

Brook Lopez is Milwaukee’s other top free agent this offseason and retaining him will also be a priority. The 15-year veteran just had arguably the best season of his career where he finished second in Defensive Player of the Year voting. He remains extension-eligible through June 30 for up to three years, $54.1 million, which would put his annual salary on par with other defensive centers like Myles Turner, Mitchell Robinson, and Clint Capela. The over-38 rule limits his extension to three additional seasons but he could get around that and sign a four-year deal with the Bucks as a free agent.

Extension candidate: Giannis Antetokounmpo

David Butler II-USA TODAY Sports

Giannis Antetokoumpo is about to reach the three-year anniversary of signing his supermax extension which the Bucks. This means he will soon become extension-eligible again. He would only be able to sign it during a limited time between September 22 and the first day of the regular season, and he would be limited to adding two years and roughly $113 million.

Maximum extensions with three years left on a player’s contract are uncommon with Damian Lillard being a rare example of doing so last season. Antetokounmpo seems likely to bypass an extension and sign a new long-term deal once he’s at the end of his current deal, but the Bucks will likely offer it as a formality.

2023-24 SALARY SITUATION

Players rostered: 8

Guaranteed salaries: $157.9 million

Non-guaranteed salaries: $0 million

Total salary: $157.9 million

Luxury tax space: $4.1 million

Apron space: $5.9 million

Second apron space: $16.4 million

Spending power:

  • Taxpayer Mid-level: $5 million (will be eliminated if/when they cross the second apron)

Giannis Antetokounmpo

Petre Thomas-USA TODAY Sports

2023-24 salary: $45,640,084

Remaining salary guaranteed: $146,363,028 through 2025-26

Additional notes:

  • 2025-26 salary is a player option worth $51.9 million

  • Extension-eligible during 2023 offseason for up to two years, projected at $113.4 million

  • 15 percent trade bonus currently worth $2.5 million

Khris Middleton

(Photo by Patrick McDermott/Getty Images)

2023-24 salary: $40,396,552 (player option)

Remaining salary guaranteed: $40,396,552

Additional notes:

  • Extension-eligible through June 30 for up to four years, projected at $204 million

  • If he picks up his option, he will be eligible to extend through 2023-24 for up to four years, $220.6 million

Jrue Holiday

Jeff Hanisch-USA TODAY Sports

2023-24 salary: $36,861,721

Remaining salary guaranteed: $72,320,000 through 2024-25

Additional notes:

  • 2024-25 salary is a player option worth $39.4 million

  • $1.9 million in annual likely incentives, $4.4 million in annual unlikely incentive

Bobby Portis

(Photo by Patrick McDermott/Getty Images)

2023-24 salary: $11,710,818

Remaining salary guaranteed: $37,734,858 through 2025-26

Additional notes:

  • 2025-26 salary is a player option worth $13.4 million

  • 15 percent trade bonus currently worth $3.6 million

Pat Connaughton

Jeff Hanisch-USA TODAY Sports

2023-24 salary: $9,423,869

Remaining salary guaranteed: $28,271,607 through 2025-26

Additional notes:

  • 2025-26 salary is a player option worth $9.4 million

Grayson Allen

Jeff Hanisch-USA TODAY Sports

2023-24 salary: $9,000,000

Remaining salary guaranteed: $8,500,000

Additional notes:

  • $500,000 in annual likely incentives, $775,000 in annual unlikely incentives

Marjon Beauchamp

Daniel Dunn-USA TODAY Sports

2023-24 salary: $2,609,400

Remaining salary guaranteed: $10,124,396 though 2025-26

Jevon Carter

Michael McLoone-USA TODAY Sports

2023-24 salary: $2,239,943 (player option)

Remaining salary guaranteed: $2,239,943

Brook Lopez

(Photo by Patrick McDermott/Getty Images)

Cap hold: $20,860,464

Type of free agent: Bird (unrestricted)

Additional notes:

  • Can avoid free agency and extend with the Bucks by June 30 for up to three years, $54.1 million

Jae Crowder

Benny Sieu-USA TODAY Sports

Cap hold: $19,349,220

Type of free agent: Bird (unrestricted)

Additional notes:

  • Can avoid free agency and extend with the Bucks by June 30

Joe Ingles

Jeff Hanisch-USA TODAY Sports

Cap hold: $7,774,800

Type of free agent: Non Bird (unrestricted)

Additional notes:

  • The Bucks can re-sign Ingles to a maximum of three years, $24.5 million

Thanasis Antetokounmpo

Kirby Lee-USA TODAY Sports

Cap hold: $1,989,698

Type of free agent: Bird (unrestricted)

Goran Dragic

(Photo by Stacy Revere/Getty Images)

Cap hold: $1,989,698

Type of free agent: Non Bird (unrestricted)

Meyers Leonard

Jeff Hanisch-USA TODAY Sports

Cap hold: $1,989,698

Type of free agent: Non Bird (unrestricted)

Wesley Matthews

(Photo by Stacy Revere/Getty Images)

Cap hold: $1,989,698

Type of free agent: Early Bird (unrestricted)

AJ Green

Benny Sieu-USA TODAY Sports

Cap hold: $1,774,999

Type of free agent: Non Bird (restricted)

Lindell Wiggington

Lindell Wigginton drives the ball past Kennedy Chandler
Lindell Wigginton drives the ball past Kennedy Chandler

Michael McLoone-USA TODAY Sports

Cap hold: $1,774,999

Type of free agent: Non Bird (restricted)

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Story originally appeared on HoopsHype