Khris Middleton is the Milwaukee Bucks’ conundrum du jour, and a perfect example of the modern age question regarding a player’s “worth.” Middleton, a newly minted All-Star and Three Point Contest participant, appears stuck in the tier between an elite player and a very good one, and some might see him as the type who has virtually secured an almost instantly-regrettable maximum contract. Think Andrew Wiggins, Otto Porter Jr, Andre Drummond or Chandler Parsons. He’s better than those guys, but the dollar amount still makes some people nervous.

Following years of improvement, Middleton appears to have hit a cliff (or at least at first glance). According to Cleaning the Glass, his points per shot attempt (111.7), a tool that measures how many points per 100 shot attempts a player averages, has dropped for the first time in five years and is only better than his first season in Milwaukee (107.9).

His shot appears to have regressed as well. He was always money from downtown, typically hitting more than 40 percent of his threes. Unfortunately, he’s hitting only 38 percent this season, his second lowest number since coming to the Bucks, again according to Cleaning the Glass. It’s also the second straight year he’s shot below 40 percent from the outside after eclipsing that mark during the first four campaigns with the Bucks. To put the icing on the cake, his effective field goal percentage has dipped to the 35th percentile of all forwards.

Needless to say, this all comes at the worst time, at least for those who were in support of Middleton being re-signed no matter what, possibly earning a max contract this summer in the process.

Middleton has a player option for $13 million on the books for 2019-20, an option you’d have to be a fool to accept. Once he dives into free agency, he’s likely to get at least one (if not more) max contract offers. According to Zach Lowe, the Indiana Pacers are potentially interested in Middleton’s services.

A player with seven years of NBA experience, such as Middleton, can earn up to 30 percent of the salary cap if signed to a max deal. The last 2019-2020 cap projection was $109 million, which means he’d make a starting salary of over $32 million next season. That’s a little bit more than he’s making this year. If he signed a four-year deal, he’d make $40.5 million during the last year of his contract in 2022-23. It’s safe to say that’s what scares his critics the most.

However, to look solely at the amount of money he’d make risks inaccurately assessing the situation.

It’s completely acceptable to say Middleton making $40 million isn’t great value, but if that’s what he signs for, that’s what the market is determining as his worth. Value and worth are different, and the value of his contract shouldn’t be the debate. Instead, the conversation should be focused around what else would the Bucks do with that money if they don’t use it to sign Middleton.

The top of the 2019 free agent class is loaded with elite players like Kevin Durant, Kyrie Irving, Kawhi Leonard, Kemba Walker and Jimmy Butler. Few would debate that Middleton is a tier below those guys, who also happen to be well beyond the Bucks’ current financial range.

Middleton falls in the second tier that includes Nikola Vucevic, Tobias Harris, Kristaps Porzingis (who may accept the qualifying offer) and D’Angelo Russell. But here too, the Bucks have no viable alternatives; thanks to the CBA and the salary cap, Milwaukee has no chance of replacing Middleton with any of these players due to cost, partly as a consequence of so many contributors approaching free agency this summer.

At first glance, the Bucks appear to have only about $91 million in salary obligations on the books for 2019-20, and that figure includes both Middleton’s player option and the entire value of George Hill’s mostly non-guaranteed $18 million (if waived by July 1st, Hill is owed only $1 million). If you remove both of those figures, the Bucks’ salary figure drops down to roughly $61 million. Time to start printing money to pay “more deserving” max players, right?

Wrong. Even though they’re free agents, players with Bird rights have a “cap hold” that serves as a placeholder on the team’s salary sheet, but it doesn’t show up on basketball-reference. If you want to remove a cap hold, you have to also renounce your “claim” to re-sign the player, thus losing his Bird rights and fully cutting ties, for all intents and purposes. Bird rights are what let you go over the salary cap to retain your own guys, so teams are not keen on missing out on these opportunities.

Without Bird rights, you have to use cap room to sign anybody to a non-exception deal, of which there are only a few available. With Middleton (assuming an opt-out, a cap hold of $19.5 million), Eric Bledsoe (cap hold of $22.5 million), newcomer Nikola Mirotic (cap hold of $18.75 million), and Malcolm Brogdon (as an RFA, he has a super-low cap hold of only $3 million) all still on the books, that $61 million figure from earlier is suddenly over $125 million...which puts Milwaukee over the cap. Renounce Middleton’s cap hold? You’re still at around $106 million, with barely any room under the salary cap, which is once again projected around $109 million. Jon Horst has pulled off some tricks, but is he expected to replace Middleton with only $3 million in space? Or is sending Bledsoe packing worth having around $25 million in space; can you really replace two major contributors for the price of one? And we haven’t even begun to discuss how the Bucks might pursue retaining Brook Lopez.

But remember, it’s not just about the money, If the Bucks choose not to pay Middleton, they won’t have anyone to replace his production on the court. Internally, it’s unfair to expect someone like Tony Snell, Sterling Brown, Donte DiVincenzo, Pat Connaughton or any odd mixture of those guys to replace what Middleton does on both ends of the floor. Additionally, while each of them have some talents that are helpful, they do not consolidate those talents into one roster spot the way Middleton does.

The other top free agent wings include Bojan Bogdanovic, JJ Redick, Danny Green and Terrence Ross. Bogdanovic is probably a tier or two ahead of the rest of the group, but each has a flaw more pronounced than the next. If Milwaukee replaces Middleton with one of them, it’s a clear step backward in talent.

Despite some fans’ passionate pleading for the Bucks’ front office to not offer Middleton a max deal, Milwaukee would be absolute fools not to.

Middleton is only 27-years-old and, on a per-36 minute basis, is playing the best basketball of his career, percentages be damned. His 19.8 points per 36 minutes is the second-highest of his career and his 4.9 assists and 6.8 rebounds are both career-bests. If he signs a four-year deal at the end of this season, he’ll still only be 31 by the time it expires. This is a great age range to offer a player one final huge contract...and the Bucks can cross that bridge when they come to it.

Middleton has earned the respect of players and coaches from across the NBA landscape; not just on his team. Gregg Popovich had this to say about Middleton’s Team USA invitation last summer in Eric Nehm’s recent article on The Athletic:

“Just understand you belong. That’s why you’re here. If you didn’t belong, you wouldn’t be here.”

Kevin Durant also chipped in:

“It’s tough to find something he can’t do. That’s the sign of a complete player to me.”

A complete player indeed. Middleton plays the demanding role of carrying a heavy offensive load while defending the opposing teams best wing every single night. Middleton’s matchups include guys like Jayson Tatum, Kawhi Leonard and Jimmy Butler.

Individual defensive numbers are hard to measure. The best defenders typically get matched up with the best offensive players which can deflate their counting stats. However, the tape doesn’t lie and, when he’s locked in, Middleton is as good as ever on defense. Despite not being elite in any of the categories, he has a nice blend of strength, lateral quickness and length that makes it tough for any wing to score on him.

With that being said, Second Spectrum’s imperfect matchup stats give us some hints on how players fair against Middleton. For instance, Leonard is only averaging 12 points on 47.7 possessions per game when Middleton is his primary defender. Durant only averaged nine points on 42.5 possessions. For the most part, Middleton does very well against elite offensive players at his position.

Middleton’s offensive prowess also make it easier on his teammates. The same Leonard’s and Butler’s that he’s defending are guarding him on the other end of the floor as well. This knocks everyone down one in the food chain and gives his teammates more favorable matchups to take advantage of.

Offensively, his shooting percentages are down. However, it’s been said before and deserves to be said again, Khris has been asked to change more than anybody else. Just last season, 52 percent of his shot attempts came from the mid-range, ranking in the 100th percentile for his position according to Cleaning the Glass. He’s dropped that number 16 percent in an effort to fit in with Mike Budenholzer’s new offensive scheme. Nearly all of those shots are going to the perimeter where he’s increased his frequency by 11 percent.

He still shoots it well from above the break where he connects on 39 percent of his looks. Even though his catch-and-shoot percentages have dipped, 39 percent on 3.6 attempts last season compared to 35.1 percent on 3.1 looks this year, his pull-up shooting has sky-rocketed.

Middleton is taking and making more pull-up threes than ever before. He’s draining an astonishing 40.1 percent of his pull-ups compared to 28.8 percent in 2017-18. For comparison, Irving is shooting 40.5 percent on the same amount of pull-ups per game.

Give Middleton time and his catch-and-shoot percentages will come back up to the elite level they were just two years ago.

No matter which tool you use, the results are clear: The Bucks are better with Middleton than without. Cleaning the Glass has Milwaukee as +5.2 points per 100 possessions better with him on the court. That ranks in the 83rd percentile. If you use NBA.com’s on/off court stats, the Bucks net rating drops from 11.3 to 6.3 when Middleton heads to the bench.

His game is also a great compliment to Antetokounmpo, as The Ringer’s Jonathan Tjark’s points out:

They are the rare one-two punch that can threaten the defense simultaneously from different areas of the floor. They aren’t as redundant as Joel Embiid and Ben Simmons, who are both at their best with the ball in their hands in the paint. Nor are there many defenses with the size on the perimeter to match up with Giannis (6-foot-11 and 242 pounds) and Middleton (6-foot-8 and 222 pounds). Not only do their games fit well together, but there aren’t any chemistry issues that can occur when two big-time scorers play together. Middleton has accepted a smaller role in the offense without complaint.

In spite of his shooting struggles, Middleton’s finding other ways to affect the game. His assist percentage is the highest of his career at 18.4 percent. Furthermore, his assist to usage ratio, another Cleaning the Glass tool that measures how often a player got an assist compared to how much they had the ball, is the second highest of his career and ranks in the 78th percentile.

At the end of the season, the question isn’t whether Middleton fits in the definition of a true max player. The NBA salary cap has created a situation where stars such as LeBron James and Antetokounmpo can’t earn their true worth. At the same time, their suppressed contracts are then used as measuring sticks for guys like Middleton.

The Bucks aren’t in a vacuum when negotiating a contract with Middleton. Instead, their options are to either overpay him to stay, or lose him without a viable replacement. The real question isn’t if he’s worth the max, but is it the best the Bucks can do with the money they have available?

Envision Antetokounmpo’s perfect partner in crime. The traits you’ll likely describe is someone who can spread the floor and shoot from the outside, create their own shot, is willing to play second fiddle and let the Greek Freak go to work, and is a capable wing defender. Well, Middleton checks all those boxes.

In just two short years, Milwaukee will be looking to re-sign Antetokounmpo. When that time comes, they’ll have to look him in the eye and tell him they did everything they could to put a winner around him. They won’t be able to make that argument if they let their team’s second-best player go in his prime with no plan to replace him.

Going back to Eric Nehm’s article, Dwyane Wade said it best when discussing Middleton,

“You have to understand his game and respect his game. Everyone’s not Giannis. Everyone’s not LeBron James. Everyone’s not James Harden. Khris is a very talented player. What he does and what he brings to the game is different than those guys.”

If the Bucks are smart, they’ll do everything they can to sign Middleton to a max contract. Because he’s that damn important.