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

The 2023 Milwaukee Bucks’ season came to an abrupt end against the No. 8 seed Heat in five games, and they may go down as one of the greatest teams in modern history to be defeated in the first round. Giannis Antetokounmpo’s back issue provided Miami with a window of opportunity to steal two games, and the Bucks were unable to recover. They now have to deal with losing a season from their title window as they approach the summer.

The Bucks were already approaching a turning point in their history because it would become increasingly expensive to maintain their core. This team’s ownership has already extended far into the tax, but it’s unclear exactly where they might draw the line. Could they have suffered early-season cap casualties after being eliminated from the playoffs too soon?

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

Milwaukee has eight players under contract going into the offseason, and the team is only $4.1 million over the anticipated $162 million luxury tax threshold. Jevon Carter and Khris Middleton are expected to exercise their respective player options in this forecast. The Bucks would still be expected to operate over the cap even if both players choose to opt out and walk. This means that their top summer goal should be to hang onto all of their most valuable free agents.

Milwaukee anticipates spending $16.4 million less than the second-best estimate, but once their roster is complete, they should surpass it. By doing this, they will lose access to the taxpayer mid-level exception and be able to only receive 110 percent of their salary back in trade returns. Re-signing their own free agents, adding minimum players, and selecting the 60th overall pick in this year’s draft are the only additional ways they may raise their payroll.

This season, ownership paid a franchise-high $83 million in penalties after going deeply into tax. They are scheduled to go into the repeater tax for 2023–2024 since they were taxpayers for three seasons in a row. Even if they have a similar payroll, this would result in an additional dollar being added to each tax level, greatly increasing their penalty. $30 million more would have been required from them in taxes if they had been subject to the repeater tax in 2022–2023.

It is unclear how much ownership is willing to invest in the repeater tax. If they want to have a chance to contend the next season, they will need to re-sign a number of important free agents. The Bucks may pay taxes totaling $125 million if they re-sign Brook Lopez, Joe Ingles, and Jae Crowder and sign two players and their second-round pick to minimum contracts. Their combined payroll and taxes would come to slightly over $315 million as a result.

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.