Here are some words that almost every Milwaukee Bucks fan never thought they would utter: Thank God for Jimmy Haslam. When the controversial owner of the Cleveland Browns bought Marc Lasry’s 25% share of the team before the 2023-24 NBA Playoffs, many fans were extremely unhappy.

Haslam’s Browns gave quarterback DeShaun Watson, who was sued by over 20 women for sexual misconduct, a guaranteed $230 million contract. For many, giving an athlete with the questionable character Watson has was immoral mistake.

What it proves, though, is that Haslam is not shy about spending money. Lasry, whose share he bought, had reportedly grown tired of Bucks’ big-spending and was advocating for slashing payroll.

Slashing payroll would mean many things, the worst of which would be Giannis Antetokounmpo leaving Milwaukee. When the rest of the ownership group fought that notion, Lasry sold his share to Haslam.

And now that the Bucks have acquired seven-time All-Star Damian Lillard, it is a good thing the free-spending billionaire is here.

The Milwaukee Bucks Will Be Paying Damian Lillard Hundreds of Millions of Dollars Over the Next Four Years

The recently acquired Lillard has two years and $94.4 million left on his original four-year $176 million contract he signed with the Portland Trailblazers. This deal kicked in at the start of the 2021-22 NBA season.

Additionally, Lillard signed a two-year $122 million extension in July of 2022. The last year of this contract is for the 2026-27 NBA season, when Lillard will be 37 years old, is a player option estimated to be worth $63.2 million.

It is hard to see a scenario in which he does not pick up that option.

So, over the next four seasons, the Bucks will pay Lillard:

• 2023-24: $45.6 million
• 2024-25: $47.7 million
• 2025-26: $58.5 million
• 2026-27: $63.2 million

Total: $215 million

The Milwaukee Bucks Are Still Hoping to Sign Giannis Antetokounmpo to a Contract Extension

The amount of money that Lillard is making seems astronomical, and it is. This is because he signed these contracts with the Trailblazers, the team that drafted him. NBA rules allow teams to sign their stars for more money than other teams can. Had Lillard been a free agent, the Bucks would not have been able to offer him that much money.

But they can offer Giannis that kind of money, and they most certainly will. For all the talk of Giannis potentially leaving Milwaukee, it realistically is not something that can or will happen for at least two more years. The way many media personalities talk about it, he has one foot out the door already (even after the Lillard trade).

The fact of the matter, though, is that Giannis still has three years left on the five-year $228 million supermax contract he signed prior to the 2021-22 season. The last year of the deal, 2025-26, is a player option. Over the next three years, Giannis will make salaries of:

• 2023-24: $45.6 million
• 2024-25: $47.7 million
• 2025-26: $51.9 million

Now, Giannis could sign a three-year extension worth $173 million this year if he wanted to; however, he has already said publicly that it does not make sense for himself or the organization for an extension to be signed this year.

According to Spotrac, there are two different contract extensions Giannis could sign in 2024:

• Giannis picks up his player option for 2025-26 and signs a three-year extension worth $194.8 million. In these three seasons, Giannis would make:
  • 2026-27: $60.1 million
  • 2027-28: $64.9 million
  • 2028-29: $69.8 million
• Giannis declines his player option and signs and four-year extension worth $244.9 million. In these four seasons, Giannis would make:
  • 2025-26: $54.7 million
  • 2026-27: $59.0 million
  • 2027-28: $63.4 million
  • 2028-29: $67.8 million

The first option would pay Giannis $295.5 million from 2024-2029.

The second option would pay him $293.7 million from 2024-2029.

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