NBA Players Under the Most Pressure Entering Contract Years

Grant Hughes@@gt_hughesNational NBA Featured ColumnistSeptember 16, 2018

NBA Players Under the Most Pressure Entering Contract Years

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    Every NBA career is finite, and every player's earning potential runs out eventually. That's why contract years come laden with so much pressure.

    Whether a player is gunning for a max deal, trying to prove he still belongs in the league or something in between, the final year of an agreement is pivotal. Perform, and you earn security. Flop, and your career could head down a less certain path where, before you know it, you're playing for the Shanghai Sharks.

    The guys we're listing are mostly safe from landing in lesser leagues. In fact, most are household names whose notoriety raises the stakes of their upcoming contract years. There are, collectively, the better part of a billion dollars hanging in the balance for the players on our list.

    So, you know, no pressure.

Kawhi Leonard, Toronto Raptors

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    Kawhi Leonard never looked like himself during the nine games he played for the San Antonio Spurs in 2017-18, even if his per-36-minute production was right in line with his typically high levels. Other than a dip in scoring efficiency that could have been the result of a small sample, Leonard contributed to winning just like he did when he finished third in MVP voting the season before.

    In light of that, maybe Leonard doesn't belong here. Maybe it doesn't matter what the 27-year-old two-time Defensive Player of the Year does during his one-season (probably) rental with the Toronto Raptors.

    Except...that doesn't feel true, does it?

    If Leonard can't get healthy, that's obviously going to change his future. One season lost—under admittedly odd circumstances that often seemed to have little to do with his health—might not chill market value. But two? That'd ding Leonard's earning potential in a serious way.

    The Raptors are poised to win the Eastern Conference and reach the NBA Finals. On paper, they're that talented. Of course, that's if Leonard contributes a full season at the level we've come to expect.

    If all goes well, there'll be no shortage of max offers out there. There'll certainly be one from the Los Angeles Lakers.

    But if Leonard misses significant time with that bothersome quad or if he plays plenty but looks considerably diminished, who knows where that might lead.

    One-year deals until he proves himself? A year or two on the mid-level exception? Surgery? The end of Leonard as an elite player forever?

    It's all on the table ahead of Leonard's unrestricted free agency (player option) in 2019.

DeMarcus Cousins, Golden State Warriors

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    DeMarcus Cousins shares Leonard's injury concerns, but the range of possible outcomes feels even greater as his contract year approaches.

    Cousins is unlikely to play for a significant portion of the season, so his window to prove he's recovered from that devastating Achilles injury won't be open for long. If he returns in February, that'll leave less than half a season for his showcase.

    Consider too that Cousins will have to integrate himself into the Golden State Warriors' high-functioning scheme without stepping on the toes of four other All-Stars. He'll be playing a smaller role than ever, and he will almost certainly find himself riding the bench in the minutes that matter most—because that's when the Dubs go small and wreak havoc.

    Potential buyers will have no choice but to make their decisions on Cousins without complete information. Suitors will scrutinize his mobility and wonder whether he's still fit to command a large role (and a larger salary) as a No. 1 option.

    Cousins' time in Golden State is a stopover. The Warriors have nowhere near the financial flexibility needed to make him part of their longer-term plans, which means they're really not incentivized to worry about his happiness.

    If things don't look good early on—if Cousins isn't quite healthy or if injury hasn't quelled his notorious bristliness in the locker room and on the floor—the Warriors can sit him down and forget he's there, which wouldn't be ideal for a player hoping to prove he's worth one more fat contract before he exits his 20s.

    The Warriors and Cousins can help each other, but if Boogie isn't productive or cooperative, Golden State has little reason to be patient. Remember, the Warriors don't need him.

    Good health and improved behavior could land Cousins a multiyear deal and a shot to lead a team again in 2019-20. In the age of center marginalization, though, anything less could result in him scrounging for one-year deals in perpetuity.

Kyrie Irving, Boston Celtics

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    A five-time All-Star, NBA champ and top-flight offensive weapon at age 26, Kyrie Irving would seem to have nothing but good options ahead of him when he hits free agency (via a likely opt-out) in 2019.

    Health is a factor, though, as Irving missed the Boston Celtics' 2018 playoff run because of a knee injury that required surgery. It wasn't the first operation for Irving, who's sat out 24 percent of his games since entering the league in 2011-12.

    Prospective free-agent suitors, factor that in. You're going to pay Irving to miss one of every five games—and that's if advancing age doesn't result in more time off.

    The Celtics nearly reached the Finals without him, and they seem to have a player in Jayson Tatum (or perhaps two if you really believe in Jaylen Brown) to headline the franchise marquee for years to come. Let's not forget Boston's white whale, Anthony Davis, who'll be linked to the team by rumor until he ends up in green or signs a huge deal with another organization in 2020.

    Maybe Irving is expendable because Davis is Boston's guy. Maybe Kyrie plans to opt out of his contract and sign with the New York Knicks after this season. It's all on the table.

    Irving has looked like himself in offseason pickup action, so he could be set up for the best season of his career—one that would force the Celtics to unload the Brink's truck they never took out of the garage for Isaiah Thomas. He is talented enough to convince Boston he, not Davis, is the in-prime veteran superstar it needs.

    Or, Irving could miss a bunch more time, the Celtics could carry on just fine without him, and he could hit a free-agent market that might not be certain he's worth a cornerstone-level investment.

Khris Middleton, Milwaukee Bucks

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    You could probably cause a stampede of unusually tall men by announcing that you were having open tryouts to be the Milwaukee Bucks' second option. It's going to be a hot gig as Giannis Antetokounmpo begins his perennial-MVP reign of terror this season.

    Who wouldn't want to be Scottie Pippen to Giannis' Michael Jordan? Dwyane Wade to Giannis' LeBron James?

    Fortunately for Khris Middleton, he's already first in line.

    All he has to do now, in a contract year—Middleton can and should exercise his opt-out this summer—is prove he's the best three-and-D secondary star available.

    The Bucks owe it to themselves to be picky. Antetokounmpo is a once-in-a-generation star with skills we've never seen in a player his size. Messing up his supporting cast as he hits his apex would be a high crime.

    Middleton, 6'8" and about a month removed from turning 27, was a very good NBA starter last year. He averaged 20.1 points, 5.2 rebounds, and 4.0 assists while playing all 82 games. He's been an advanced-metrics darling forever, though.

    In 2014-15, Middleton ranked 10th in ESPN's real plus-minus. The following year, he was 20th. Injuries hit in 2016-17, limiting Middleton to only 29 games (23 starts), and though he slipped on D, he still ranked 25th in offensive RPM last year.

    A career 39.1 percent shooter from deep and a serviceable defender who should excel in a switching scheme, Middleton would start on virtually any team. He'll certainly start for the Bucks, but it may take a career year from him to solidify his position with the franchise going forward.

    Milwaukee refused to spend on Jabari Parker, which suggests the Bucks aren't going to settle for just anyone as Antetokounmpo's long-term running mate. 

    It's up to Middleton to prove he can take his game to a new place. Otherwise, the Bucks would be justified in moving on as someone else winds up paying Middleton $20 million per season. That's hardly a bad outcome, but it doesn't sound nearly as fun as earning something close to the max as a superstar's second option.

    Put it this way: If you were Middleton, wouldn't you want to do everything in your power to stick around with the Bucks when things get really good?

Justise Winslow, Miami Heat

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    So is it ever going to happen for Justise Winslow?

    This feels like a ridiculous question to ask of a 6'7" 22-year-old who's already proved himself as an above-average defender (with room to get much better than that) and passer. Winslow shot 38 percent from deep last year. I mean, what else does he need to show?

    A lot, actually. Especially if he wants to up his earning potential ahead of restricted free agency in 2019.

    Winslow started just 25 of the 68 games he played for a 44-win Miami Heat team last year, and we'd be remiss if we didn't first address his shooting. Though Winslow crushed his previous season best of 27.6 percent from three in 2015-16, the shooting breakthrough came on a shade under two attempts per game.

    That's still pick-your-spots volume, and while it's encouraging, modern wings with an eye on stardom need to inspire much more fear in a defense.

    If Winslow develops an off-the-bounce shot from deep, it'll transform his game and balloon his value. If he continues to look like an on-the-margins contributor with real offensive holes, it's hard to know what he'll command on the market.

    Though it sounds like an oversimplification, Winslow must become a regular starter in 2018-19. If he grows his offensive game enough to earn that role and if he shows steady improvement while shouldering larger responsibilities, he could cash in.

    There's a viable scenario in which a more developed version of Winslow becomes a Swiss-army-knife star, capable of initiating the offense as a point guard or spacing the floor on the wing while defending five positions. That kind of talent is practically priceless.

    Of course, there's also a future in which Winslow is a useful defender who only chips in once in a while offensively. You know, the kind of player who starts just 25 games for a middling club.

    It's probably best to be bullish about a 22-year-old with such obviously valuable tools. But we've had three years of mostly underwhelming growth, so Winslow's range of outcomes remains broad. The only certainty is that Winslow's play this season will define his future.