Khris Middleton's Pending Free Agency Is More Interesting Than You Think

Bucks' Khris Middleton is one of the NBA's most underrated players and his contract has been a bargain for Milwaukee. Here is why he should demand a lot of attention during the 2019 NBA free agency period.

In Game 1 of the Bucks-Celtics playoff series last April, Khris Middleton had 31 points on 12-20 shooting, including 5-7 from three-point range. He added 8 rebounds, 6 assists, and 2 steals. He played 47 minutes of a game that went to overtime, and if you remember anything about this game, it's probably that Middleton hit a 35-foot three to tie it at the end of regulation. The entire game was a wake-up call for anyone who had assumed Giannis Antetokounmpo would always be the only star in Milwaukee. It was the beginning of a breakout story that Middleton has continued this season. 

The Bucks return to Boston Thursday night with the best record in the NBA. At 7-0 under new head coach Mike Budenholzer, the entire team looks worlds better than last season. Giannis is an MVP candidate who already looks superhuman, the rotation goes 8 deep with solid contributors, and Budenholzer will be a Coach of the Year candidate. On that last point: this Bucks season will be many things, but whatever happens next, the first month has been an emphatic rebuke of every hamfisted strategy the team employed under Jason Kidd. (As Malcolm Brogdon said of the new coaching staff during training camp, "They're very detail oriented, but at the same time they're very enthusiastic, they're very positive. Their approach is just so different than what I've experienced in terms of being encouraging, being uplifting.")

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There's also Middleton, the 27 year-old wing next to Giannis. He's currently averaging 20/5/4 on 50% shooting and an unsustainable-but-still-obscene 55% from three-point range. Assuming he exercises the opt-out in his current contract, he's going to be a free agent next summer, and as he enters his seventh NBA season next year, he'll be eligible for a max deal that starts around $30,000,000. And, I know this is a tough sell, but Khris Middleton's free agency might be one of the biggest stories in the entire league. It's a window into several different discussions that have NBA teams on tenterhooks at the moment.

The first question: who wants to pay Middleton? In theory, and especially considering a 2019 free agent class that's already looking a bit thinner than expected, Middelton should be a target for any contender in the NBA. For example, if a team like the Lakers can't use its max cap space on Klay Thompson or Kawhi Leonard or Kevin Durant, wouldn't Middleton be an ideal consolation prize? Imagine Kentavious Caldwell-Pope, but a player who's ten times better at all the things Caldwell-Pope is supposed to be good at. Middleton isn't quite a superstar and he won't take over games on a regular basis, but that's what LeBron is for. If the Lakers could sign Middleton and somehow pull off a trade for Anthony Davis, next summer becomes a home run. Even if they can only land Middleton, the team would enter next making a lot more sense.

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It's not just the Lakers, either. The Sixers struck out after entering last summer with cap room to sign a superstar. Hitting on another superstar free agent does not look promising this summer. After that, the roster will get expensive and it becomes harder to build around Joel Embiid and Ben Simmons. What if Philly turned all its attention to Middleton? Likewise: What about the Utah Jazz? Rudy Gobert and Donovan Mitchell still need a little bit more help on offense, and Middleton's two-way game would be a seamless fit with everything that's made the Jazz great the past few seasons. Would it make sense to see what's possible?

Or the Mavericks: Dallas has needs to address at center (if DeAndre Jordan leaves) and possibly point guard, but building a starting lineup of Harrison Barnes-Luka Doncic-Khris Middleton would be a good place to begin the next phase of the franchise. Even the Nets: That team has been operating in no man's land for what feels like a decade, but Brooklyn has a ton of money to spend over the next few years, and an underwhelming draft class in 2020 could reduce the incentive to tank. If Durant and Kyrie are off the table for the Nets, Middleton could be a nice bridge to 2020 and beyond. 

In general, Middleton's free agency underscores just how many teams will enter this summer convinced they are one piece away from moving to a new tier of the league. And more than anything, considering how well he'd fit on a dozen different teams is the most convincing way to explain Middleton's value in Milwaukee.

The Bucks will do everything they can to re-sign him. Milwaukee has spent the past few seasons doing its best to ignore Giannis Antetokonmpo 2021 free agency rumors, and losing Middleton without a viable replacement would almost be like forfeiting the Giannis battle before it even begins. As recently as a month ago there was hope that Middleton's annual number would land somewhere in mid-20s—not the full max—and afford Milwaukee some extra flexibility to retain fellow '19 free agents like Brogdon and Eric Bledsoe. Those dreams are likely over now. After a few weeks seeing what his game looks like under a competent coaching staff, it seems clear there will be enough competition for Middleton to get him to a full $30 million max. Convincing him to a take a discount is also unlikely; Middleton already did that when he and his agent re-signed at a slightly below-market 5 years/$70 million in 2015. (This was at the height of the NBA's "Jeff Schwartz is shadow president of the Bucks" rumors. What a time.)

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"Right now I’m just going to play out my contract,” Middleton told Michael Scotto and The Athletic last May. “I’m not going to put any pressure on myself or think about opportunities that could come up sooner. The way I got to where I am today is taking one day at a time and focusing on my game. Everything will take care of itself once you win."

“To be a Milwaukee Buck," he added. "It’s a great feeling. It’s a unique feeling. It’s a small-city market, but when you live there and you play there every night you realize how much you mean to that city and how much you can do to impact people’s lives around there."

For the sake of argument, let's assume Middleton spurns L.A. and Philly and stays in Milwaukee, because that seems like the most likely outcome. In that case, any discussion of Middleton's free agency also includes one question that may not be asked until midway through next season. Are we sure Khris Middleton is worth $30 million-per-year? All told, he will be eligible to sign a 5-year deal that will be worth around $177 million. He's been excellent all season, but even as he's cut down on midrange jumpers and hit an all-time high from three-point range, there are reasonable questions about how far that would eventually take Milwaukee. 

The most recent collective bargaining agreement has come under fire for a number of reasons, but as counterproductive as supermax contracts have been, there are also less-infamous max contracts for veterans who re-sign with their incumbent teams. In the same way that supermax deals allow hometown teams to offer more money but also force those teams to keep all that extra money on the salary cap, any star who re-signs on a traditional max deal will be granted an extra year (five years vs. four years) and up to 8% in annual raises (compared to 5% on a max deal with a new team). This is designed to give home teams an advantage in free agency, but that advantage becomes a burden as soon as stars actually sign. (The raises in those deals were designed to account for rises in the salary cap, but as the cap has flattened, the raises tend to exceed any cap inflation.)

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Ultimately, it leaves teams like the Bucks in a tricky spot. They have no choice but to pay Middleton whatever they can, but building the rest of their team becomes complicated from there. If bringing back Middleton means Giannis eventually re-signs in Milwaukee on a supermax contract, that's a dream. But even in that best case scenario, the Bucks would be paying 60% of their salary cap to two players. In that case, Middleton would have to be even more incredible to give the Bucks a real chance at a title. That's not a shot at Middleton, either--how many titles would the Warriors win if unlucky cap timing meant they could only pay Steph Curry and Klay Thompson?

Middleton's value this season is in part due to the contract he signed a few years ago. A contract that pays him $13 million in 2018-19 makes Middleton arguably the best bargain in the league. That equation will become more complicated going forward. If Middleton signs elsewhere, he could join a team as a slightly overpriced third superstar, and perhaps he'd have a better shot at winning a title; in Milwaukee, he'll be an even more expensive sidekick to a perennial MVP candidate, and with the clock ticking on Antetokounmpo's free agency, he'll have to prove that he's good enough to give Giannis a real title shot in Milwaukee. 

All of this is a reminder of how hard it can be contend in today's NBA. The path involves high stakes choices for players and teams, and the CBA hasn't made it any easier, and timing is crucial for everyone involved. The Bucks have the odds stacked against them, but only because the odds are stacked against everyone. And in that case, it's worth remembering that Milwaukee looked hopeless last April. Giannis was out of the playoffs in the first round. The bench was a disaster. The coaching staff had no answers. It didn't matter that Middleton had the series of his life against the Celtics.

Eight months later, things are getting a lot more interesting.