Milwaukee Bucks: What should a Khris Middleton extension look like?

Perhaps the most fascinating decision that the Milwaukee Bucks could make this offseason is whether or not they want to extend Khris Middleton.

Middleton and Brook Lopez are both going to be extension eligible this offseason and while Lopez is a pretty obvious case for an extension, there’s actually some debate around Middleton and what the organization should do with him.

Should the Milwaukee Bucks extend Khris Middleton?

I’m not so sure this answer is as clear-cut as it was with Lopez.

Middleton is a better player than Lopez and we saw how much the Bucks missed Middleton’s half-court creation ability against the Boston Celtics. Don’t let anyone fool you, they didn’t lose that series because they didn’t have P.J. Tucker. Would he have helped? Sure, but they lost that series because they didn’t have Middleton and couldn’t score enough consistently in the half-court (they had an offensive rating of 81.9 in half-court possessions per Cleaning the Glass).

Middleton, though, will be 31 at the start of next season and we’ve seen some signs of decline in the last few seasons. After posting a career-best 57.5 percent effective field goal rate in 2019-20, he has seen that number drop in the following two seasons to 52.2 percent this past season.

He shot 54.6 percent on 2-point shots in 19-20 which fell to 49.4 percent this season and only 37.3 percent on 3s after being above 41 percent the previous two seasons.

The argument could be made that this season Middleton was dealing with injuries and illnesses that threw off his rhythm and was coming off of a very shortened offseason after playing over 42 minutes a night in the Finals and then going to the Olympics. But we have to at least consider that Middleton is declining a bit.

If he is, do you trade him? I don’t know what Middleton’s value would be on the trade market but you’re likely not getting enough back to make up for trading your second-best player and best shot creator.

So, the question is should the Bucks extend him. You’re not going to let him leave in free agency after next season and get nothing so yes, they should extend him if they aren’t going to trade him. He helps maximize Giannis Antetokounmpo’s championship window and is their best halfcourt creator.

What should a contract extension for Khris Middleton from the Milwaukee Bucks look like?

This all starts with Middleton’s player option for next season. Milwaukee can add three years onto his deal if he accepts the player option or four if he declines the $40.4 million option. However, if he does decline it, then the starting salary in the first year of his extension can’t be less than the declined option. There are no restrictions if he accepts the option.

So they’re paying him at least $40.4 million in 2023-24 no matter what. That’s part of the reason why the Bucks wouldn’t get reasonable value back for Middleton because there won’t be many teams that are comfortable with that number.

Assuming he accepts the player option, how comfortable will Milwaukee be paying a guy who may be showing signs of decline and will be 33-years-old in the first year of that extension?

ESPN’s Bobby Marks suggested a two-year deal worth $50 million and a starting salary of $25 million in the first year of the extension.

DeMar DeRozan will be 33 in the second year of his contract with the Chicago Bulls. He’s coming off of an All-NBA season at 32 that no one saw coming. DeRozan’s game has evolved over the years and he’s gotten better with age. Will we see the same with Middleton?

Again, though, it will be hard to get fair value for Middleton. He’s always been someone more valuable to the Bucks than any other team. You can pitch your Damian Lillard trade ideas, but is the trade to make the Bucks better going to be by getting smaller after what we saw against the Celtics?

Milwaukee has zero wing depth behind Middleton and that’s part of the reason why they can’t really afford to let him go without any sort of wing-sized player coming back in return or already being on the roster.

You can have your opinion on whether or not Middleton is worth an extension but the fact of the matter is that he’s their only good wing player. He might be declining and his defense will likely get worse but this is the core that the Bucks have locked themselves into unless another team comes in with an offer that you didn’t expect.

This will be the most interesting decision of the Milwaukee Bucks’ offseason but all signs point to an extension for Middleton. It just depends on how much it will cost.