The Best Bucks Contracts of the Last Decade: Khris Middleton Cashes In at #3

As the man who seemingly inspired discussion over his next contract from the moment his 5-year, $70M deal was inked in 2015, Khris Middleton showed his worth over the length of this middling deal that grew more valuable as the cap grew like the Grinch’s heart. Ranking in the top-3 of best Bucks contracts of the last decade seems like a no-brainer. Much is left to be determined if his current contract will also go down in the annals of best deals (if he plays like this season for the duration of it, I would venture to say yes), but for now, let’s celebrate what was one of the finest pre-cap-spike contracts signed.

Middleton’s career up to this deal needs little rehashing for Bucks fans. He arrived in the Brandon Jennings sign-and-trade alongside Brandon Knight, after a relatively anonymous rookie season where he averaged 6 points and played merely 27 games. Even his 3-point shot was falling at just 31.1%. So he seemed like a toss-in for the trade, but in the rusted incubation period of that horrid ‘13-14 campaign, Khris Middleton proved his mettle by appearing in all 82 games, starting 64, and doubling his rookie point total while nailing 41.1% of his 3-point jumpers. During the team’s breakout 14-15 year, Middleton improved to 13.4 points per game, 4.4 rebounds, 2.3 assists and 1.5 steals, the start of his perception as a prime 3-and-D competitor.

Alongside Jabari Parker and Giannis Antetokounmpo, Middleton was primed to be an ideal third banana. A low-usage elite gunner who could knock down from outside and hit from the midrange when need be while guarding the opponent’s best wing player. He could swing up to the four with his length for smallball, or shift to shooting guard with his ball skills. His skillset could fit anywhere, making him a coveted free agent in 2015, even with his limited track record. Almost immediately, some snark rolled in due to the cap shifting upward a moderate amount that Summer. How little we all knew about how Summer 2016 would go...

Quickly, Middleton justified the contract. With Jason Kidd increasingly reliant on Middleton as his workhorse, he nearly led the league in minutes in 2015-16. Middleton made another mini-leap that season statistically, upping his points to 18.2, hitting 39.6% of his triples on 4.6 attempts per game, topping 4 assists and serving as a prime off-ball defender within Kidd’s frenetic scheme. Indeed, Middleton was often the defensive beneficiary of Kidd’s scheme where he could work as an off-ball safety. One only needs to look at his average steals per game during Kidd’s tenure (1.5) vs. Bud’s (1.0) to see how his role has shifted dramatically. That also could’ve inflated his defensive value a tad at the outset of his career.

Middleton’s 16-17 campaign was shortened dramatically by his hamstring taking a brief vacation from his bone, but he returned as a competent shooting option to trot out in the Playoffs against the Toronto Raptors. His subsequent two seasons featured impressive bounceback performances from that injury. Jason Kidd returned to playing Middleton to the max, sending him out for 36 minutes a clip in 2017-18. Despite that, what remains most impressive about Middleton is his seemingly continued improvement in different facets of his game, even as he aged late into this 20’s. While not Giannis-sized leaps each season, he remained steadily efficient (between 55.8-57% true shooting percentage every year of the deal) even while his usage ticked up to a then-career high 25.1% in 2018-19.

The “catch-all” statistics have fascinating opinions of Khris Middleton. Here’s where he ranked in several different ones over the course of this deal (discounting his injured campaign).

Indeed, Middleton was rarely beloved by the advanced stats until this year when his efficiency creeped towards the top of the league’s charts. Strangely enough, his best year prior to this one was mostly 2014-15, when he was an RPM darling behind the Bucks near league-best defense. The above stats were baked into some of the conversation surrounding whether he was deserving of a nearly $35M per year deal. Part of his production very well could have been muted by the quiet preponderance of mouths to feed within the Bucks’ offense while Malcolm Brogdon was in town and Eric Bledsoe was still asserting himself within the franchise.

I don’t think those catch-all stats properly illustrate Middleton’s full value. Even if his defense was overly inflated early in his career, he remains a stout, rangy wing who gave Kawhi a serviceable fight in the Conference Finals last season. What really gave Middleton the value over the length of his contract was his underrated playmaking/passing ability. His assist percentage routinely ranked in the 90th percentile or better on Cleaning The Glass among forwards.

Middleton elevated his play this year, silencing many of the concerns surrounding the massive extension Milwaukee bestowed upon him in the offseason. Kudos to Khris for continuing to play his efficient game until it earned him Max Money.

From the archives

Frank breaks down the quickly leaked details of the deal in 2015

Among other impressive statistical milestones, Middleton somewhat famously ranked tenth in the entire league in Real Plus-Minus(+6.07), reflecting the critical role he played in the Bucks’ turnaround under Kidd. The team’s best floor-spacer and most versatile wing defender, Middleton was the common cog in virtually all of the Bucks’ best lineups, and his combination of shooting and ability to defend multiple positions makes him in many ways the perfect complement to Giannis Antetokounmpo and Jabari Parker.

It’s not to say the deal is without risk — this is still a lot of money we’re talking about, and injuries infamously derailed the career of another sweet-shooting Bucks’ #22. But what Middleton lacks in flash he makes up for in practicality; he may never be an all-star, but in a league increasingly moving toward switching defenses and three-point-heavy offenses, Middleton’s shooting and two-way versatility are precisely what teams are coveting.

Brew Hoop Best Contract of the Last Decade Ranking

8. Zaza Pachulia (2013; 3-year, $15.6M)

7. Mike Dunleavy Jr. (2011; 2-year, $7.5M)

6. Jerryd Bayless (2014; 2-year, $6M)

5. Jason Terry (2016; 1-year, $1.5M)

4. Pat Connaughton (2018; 2-years, $3.3M)

3. Khris Middleton (2015; 5-years, $70M)

And then there were two. Help decide who officially has the best Bucks contract of the last decade.

This poll will close at 10 pm CST on Thursday, June 25.