Eight NBA Players Looking to Secure the Bag This Season

We still might see a few signings to round out rosters as NBA teams load up for the 2022-23 season—an Eric Bledsoe or Jeremy Lamb here, a Tony Snell or Hassan Whiteside there—but, for the most part, this summer’s free agency period has concluded. NBA front offices never stop looking ahead, though, and with the league recently projecting the 2023-24 salary cap at $133 million, you can bet they’re already mapping out contingency plans for next summer’s market.

The quality of the 2023 free agent class dipped as soon as LeBron James chose to extend his contract on Wednesday. Whether it declines further will depend largely on the decisions of several All-Stars: namely, whether James Harden, Draymond Green, and Khris Middleton pick up their 2023-24 player options or work out new long-term deals, and whatever the hell winds up happening with Kyrie Irving—in Brooklyn or elsewhere. (I note here with relish that Patrick Beverley will also be a free agent next summer, because I don’t want the smoke.) Even if there doesn’t wind up being a ton of star power at the top of the market, though, next summer’s class is poised to feature a few intriguing players who are in position to play big roles—and potentially earn even bigger bags—in the final season of their current contracts.

Let’s take a look at some of the most compelling names in the 2023 class to keep an eye on this season, starting with a Grit and Grind throwback on the next-gen Grizz:

Dillon Brooks, Grizzlies

Thanks to a little thing called recency bias, there’s an excellent chance that the sight of Brooks’s name caused you summon two memories: him clobbering and subsequently injuring Gary Payton II on a breakaway dunk in the Western Conference semifinals, and him bricking jumper after jumper during Memphis’s six-game loss to the eventual champion Warriors. Zoom out from those ugly specifics to consider Brooks’s game and standing in its broader context, though, and a sunnier picture begins to emerge—one that, if Middleton stays put and Andrew Wiggins extends his contract in Golden State, might make the 26-year-old the best two-way wing available next summer.

The Mississauga product plays like a mauling mid-century middleweight, forever leading with his chin to get into opponents’ personal space. That predilection toward physicality can get Brooks in trouble—he’s averaged 5.7 personal fouls per 100 possessions over five pro seasons—and it doesn’t exactly endear him to fans of the teams Memphis faces. It’s helped give the new-look Grizzlies an attitude and edge befitting their franchise forebears, though, and has proven quite handy for Taylor Jenkins’s defense.

Scarcely anybody routinely takes on tougher jobs than Brooks, whose list of most frequent defensive assignments reads like an All-NBA ballot. He has ranked in the 99th percentile in average matchup difficulty each of the last two seasons, according to The B-Ball Index, and Memphis has allowed fewer points per possession during his minutes in all but one of his seasons. Combine that level of point-of-attack effectiveness with a 6-foot-7, 225-pound frame that enables him to check elite perimeter playmakers across three positions—and, in a pinch, switch onto and bang with some bigs—and you’ve got a pretty solid building block. What makes Brooks even more intriguing, though, is the juice he brings on the other end of the court, particularly when it comes to pressuring the rim. He can be a force with a live dribble, producing points on 73 percent of his drives last season—ninth-best out of 139 players to average at least five drives per game, according to Second Spectrum—due partly to his ability to seek out and finish through contact.

Brooks can sometimes get too shot-happy—particularly considering he shot just 48 percent inside the arc and 31 percent outside it last season, making him one of the least accurate high-usage players in the NBA. But as ugly as it can look when he’s forcing tunnel-vision jumpers, that kind of confidence and aggression can also make him exceptionally dangerous when it’s all clicking—like when Brooks averaged a shade under 26 points per game on .595 true shooting against the Jazz in the opening round of the 2021 playoffs. And it’s not as if Brooks hasn’t been productive: While injuries limited him to just 32 games and 885 minutes last season, he was one of just 22 players to average at least 24 points and three assists per 36 minutes of floor time, according to Stathead. Of the other 21, the only one with a lower turnover rate was Klay Thompson; the only one to post a better defensive estimated plus-minus was Paul George.

It’s possible that Brooks, who’s now eligible for an extension of the three-year deal he signed back in 2020, won’t reach unrestricted free agency. But if he decides that the maximum re-up Memphis can offer him—four years, $61.3 million—doesn’t quite match what he might be able to get on the free market after watching squint-and-they’re-similar players like Luguentz Dort, Norman Powell, and Tim Hardaway Jr. all get both higher annual average salaries and more total money on their new deals, the stage could be set for an awfully interesting contract year.

Gary Trent Jr., Raptors

Only six players age 23 or younger averaged 18 points per game and shot 38 percent from 3-point range last season. Three (Trae Young, Darius Garland, LaMelo Ball) were All-Stars. One (Tyler Herro) won Sixth Man of the Year, and another (Desmond Bane) was a top-five finisher in Most Improved Player voting.

The sixth, as you surely deduced from the heading of this section, was Trent, who authored a breakout season for a Raptors team that bounced back to return to the playoffs—and who, in the process, might have put himself in position to secure an All-Star-level payday should he choose to decline his $18.6 million player option for the 2023-24 season.

Shooters get paid in the modern NBA, and Trent has proven to be a very good one, even at elevated volume. He’s drilled 37.8 percent of the nearly eight triples he’s hoisted per game since joining the Raptors at the 2021 trade deadline, including a 41.1 percent mark on catch-and-shoot looks last season. He’s more than a spot-up option, too, showing significant growth as a full-fledged scorer capable of generating good looks on his own; out of 123 players who attacked defenders in isolation at least 100 times last season, Trent ranked fourth in points per chance, according to Second Spectrum. His combination of floor-spacing and midrange shot creation was particularly helpful in decongesting a Raptors offense that tended to get claustrophobic: Toronto scored at a top-six level with him on the court, and at a bottom-six rate with him off of it.

Perhaps just as important: After coming out of Duke with a reputation as a “poor defender who ball-watches, struggles moving laterally to contain quicker players, and lacks the strength to contain bigger ones,” Trent played a significant role on Toronto’s top-10 defense last season. He now moves more attentively off the ball, using his length and quickness to track opposing shooters as they move around the half-court, and he’s become extremely disruptive, ranking tied for third in the NBA last season in steals per game and tied for fourth in deflections per game.

Sometimes, he’ll just straight up rip the ball out of opponents’ hands, because any job worth doing is worth doing viciously and with flair:

Trent still has work to do to develop his all-around game, chiefly when it comes to complementary playmaking—he’s averaged fewer than two dimes per 36 minutes in his career—and finishing on the interior. But legit marksmen who can create their own shot and defend multiple perimeter positions well enough to stay on the court in the postseason are worth their weight in gold. I’m guessing Masai Ujiri wants to see Trent spend his mid-20s north of the border. Another level-up campaign like last season’s, though, and it’d probably be in Trent’s best interest to opt out and find out just how badly Ujiri wants him—and who else might want him even more.

Victor Oladipo, Heat

Four years ago, Oladipo was coming off his first All-Star and All-NBA berths after a breakthrough season in Indianapolis as the new leader of the post-Paul George Pacers. At just 25 years old with rocket boosters in his sneakers, an advancing three-level-scoring game, an All-Defensive First Team nod to his credit, and charisma to burn, Oladipo seemed set for superstardom—and, with it, the kind of lucrative long-term contracts that serve as a handsome reward for the NBA’s best and brightest.

And then, things fell apart. A devastating quadriceps tendon injury cut short his 2018-19 season and put him on the shelf for a year. His return lasted all of 13 games before the onset of the pandemic. But whether it was before the break or in the bubble, he just didn’t look much like his previous All-Star self. A hoped-for reset in 2020-21 was interrupted by his inclusion in the James Harden blockbuster and a 20-game layover in Houston prior to a trade to Miami—reportedly his preferred destination for years—before yet another season-ending quad tendon injury once again scuttled his plans.

Oladipo returned only to play sparingly over the final month of the regular season, but he poured in 40 points in Miami’s regular-season finale and carved out a second-unit role in the postseason. The flashes he showed during the run to the Eastern Conference finals—a 23-point performance to help close out the Hawks in Round 1, three double-figure scoring nights and some stout defense against Philly in Round 2—helped Oladipo earn a new deal in Miami this summer, initially reported as a one-year, $11 million pact, but later reconfigured as a two-year deal worth $18 million total with a player option for Year 2.

From the Heat’s perspective, reducing the first-year salary helps provide Pat Riley and Co. more financial and roster-management flexibility as they continue to hunt for another star to bolster their championship chase. (Making it a two-year agreement also allows them to move Oladipo in such a deal, if need be; as Ira Winderman of the South Florida Sun Sentinel noted, a player signed using Bird rights to a one-year pact has “an implied no-trade clause” for one year.) For Oladipo, it guarantees slightly more money overall for a player who’s made just 96 appearances over the last four years … if he picks up the option.

From the sound of it, though, he’s eager to have the kind of season that’d make that decision penny- and pound-foolish. Asked during a recent appearance on The VC Show with Vince Carter what he’s looking to prove this season, to himself and to the league at large, Oladipo responded simply, “That I’m one of the best players in the world, period.”

“A lot of athletes deal with injury, but a lot of athletes come back and do very well from injury, and have great careers—even better than before,” Oladipo said. “Why can’t that be me? Why can’t I come back from this injury and what I’ve been through and have an even greater career than I thought I could have prior to it?”

If he’s finally healthy, he may well get the chance to write that next chapter. As good as Miami was last season, earning the no. 1 seed in the East before coming within one front-rimmed transition 3 of the NBA Finals, the Heat relied far too much on Jimmy Butler and Tyler Herro to unlock defenses. They could really use another ball handler capable of breaking down opponents off the dribble, attacking the rim, getting into the teeth of the defense, and creating good looks for himself and his teammates—the kind of north-south slashing and shot creation that Oladipo excelled at during his Indiana peak.

There should be opportunities for Oladipo to seize. If he can make the most of them, he’d put himself in position to go back into unrestricted free agency in a significantly stronger position than he’s been at any point since his injury. It’s unlikely that anything he puts on film this season will result in a new deal that makes up for the money he left on the table in Indianapolis and Houston. But a player looking to show the world (and, to some degree, himself) that he can still be a legit difference-maker at the NBA level has to start somewhere.

Josh Hart, Trail Blazers

Every NBA team needs players like Hart; this much has been clear since well before he ever set foot in the league. The Blazers, being an NBA team, therefore need players like Hart—which is why they both traded for and retained him over the last six months. The question now, though: Will they keep him around? Or, with the 27-year-old just 82 games away from reaching unrestricted free agency, will a rock-solid do-it-all role player prove too attractive a commodity for the Blazers to resist shopping on the open market?

After joining the Blazers at February’s trade deadline in the deal that sent C.J. McCollum to New Orleans, with Damian Lillard recovering from season-ending abdominal surgery and Jusuf Nurkic and Anfernee Simons soon to join him on the shelf, Hart seized the chance to showcase his wares. He set new career highs in touches and time of possession, and he made the most of all that on-the-ball opportunity, averaging 19.9 points, 5.4 rebounds, and 4.3 assists in 32.1 minutes per game, shooting 61 percent inside the arc and 37.3 percent beyond it on a career-high volume of long launches.

Hart thrived in a higher-usage role before being shut down himself with left patellar tendinopathy, topping 20 points seven times in his 13 games in Portland—compared to 11 times in 153 games as a Pelican, and nine in 130 games as a Laker—highlighted by a 44-point, eight-rebound, six-assist, four-steal eye-opener against the Wizards:

You’d imagine the lion’s share of those shots, touches, and playmaking opportunities will be redistributed this season to the returning Lillard, Simons, and Nurkic, as well as the incoming Jerami Grant. Hart can still be highly effective at a lower usage rate, though, serving as a connective-tissue swingman who can defend multiple positions, run a complementary pick-and-roll, fill the lane on the fast break, finish efficiently at the cup, and compete like hell on the glass. Over the last three seasons, Luka Doncic leads all wing players in defensive rebound rate; Hart ranks second.

Though he’s slightly undersized at 6-foot-5 (albeit with a 6-foot-9 wingspan) and 215 pounds, Hart may well be the most sensible pick to start at small forward next to Dame and Simons this season, ahead of fourth-year wing Nassir Little and new arrival Gary Payton II. In context, though, you wonder whether a Blazers team that spent this summer throwing boatloads of cash at other guards—a new $122 million extension for Lillard, $100 million for Simons, and $28 million for Payton—not to mention using the no. 7 pick in the draft on über-prospect Shaedon Sharpe—might think hard about showcasing Hart in the first half of what could be his walk year before exploring the market for his services come February. Especially considering his expiring contract isn’t exactly as straightforward as most:

Back in February, new Blazers general manager Joe Cronin labeled Hart a “keeper [who] embodies what we are trying to build here.” But what happens if Hart balls out to start the season? If he’s helping the Blazers vault back into the playoff mix in a crowded West, can they afford to move him? If he plays well enough to potentially put himself in position for a new deal outside of Portland’s preferred price range next summer, can a team with so much invested in the backcourt and in need of reinforcements up front afford not to?

Here’s a few other players who could put themselves in line for big paydays next summer:

• Kyle Kuzma, Wizards: After providing a slight silver lining for the woebegone Wiz with his all-around play last season, the 6-foot-9 forward finds himself staring down a $13 million player option for 2023-24. If Kuzma can maintain his stepped-up rebounding and playmaking while advancing as a defender and scoring more efficiently as a complement to the hopefully healthy top two of Bradley Beal and Kristaps Porzingis, he could draw attention as the kind of versatile big wing that good teams (like the title-winning Lakers for whom he played a key role) look to target once free agency opens.
• Christian Wood, Mavericks: The offensive numbers looked fine: 19.1 points and 9.9 rebounds per game on .593 true shooting across two seasons in Houston. The performance on the other end of the court, though—where the 6-foot-9 big man allowed opponents to shoot 63.1 percent at the basket last season, and where the Rockets finished 28th and 30th in points allowed per possession in his two seasons—left plenty to be desired. Maybe Wood’s athleticism and shot-blocking will play up on a Dallas defense that Jason Kidd overhauled en route to a surprising top-10 finish last season, allowing him to slot in as what should be a perfect pick-and-roll/pick-and-pop partner for Luka Doncic. If it does, Wood might finally cement himself as a long-term building block for a team of consequence. If it doesn’t, though, the 26-year-old nomad might find himself on the move yet again, searching for an eighth team to give him what could be a pay cut.
• Max Strus, Heat: After seeing little more than mop-up duty for Miami as the Bucks swept them out of the 2021 playoffs, Strus forced his way into Spoelstra’s rotation and never looked back, eventually supplanting Duncan Robinson late in the season and starting every game in the Heat’s run to the Eastern Conference finals. The DePaul product marries high-volume 3-point accuracy (41 percent from deep on 6.5 attempts per game, with excellent marks both off the catch and pulling up) with some more juice off the dribble and the ability to guard across the perimeter positions in Miami’s switch-heavy defensive scheme. (More effectively than Robinson, anyway.) Suitors might start getting gun-shy about giving one-way marksmen big deals after watching the contracts of Davis Bertans (five years, $80 million in 2020) and Robinson (five years, $90 million in 2021) age like milk left in direct sunlight. If Strus—who went through three two-way contracts before catching on for good in Miami, and who’s yet to make $2 million in a season—can put up another season that proves he’s a viable 3-and-D commodity deep into the postseason, an updated version of what Joe Harris got before his injuries in Brooklyn (four years, $75 million) might be in order, whether in South Beach or elsewhere.
• Jaylen Nowell, Timberwolves: The third-year combo guard out of Washington started last season buried on Minnesota’s depth chart. But injuries and illnesses opened the door for him to get some minutes in mid-December, and he made the most of them, averaging 9.8 points and 2.4 assists in 17.9 minutes per game over the final four months of the season, shooting 54 percent on 2-pointers and 41 percent on long balls. He’s got a knack for creating his own shot, ranking in the 81st percentile in points produced per possession in isolation, according to Synergy. Wolves head coach Chris Finch made a point during his post-playoffs exit interview to call Nowell “an X-factor [and] a game-changer” who merits “a more consistent role” in Minnesota’s hierarchy: “We want him to feel as [much] a part of our young core as anybody else that’s here.” The Rudy Gobert blockbuster decongested the Wolves’ backcourt rotation; Nowell likely enters training camp as Anthony Edwards’s backup, with plenty of opportunities to handle the ball and generate offense. A 23-year-old bucket-getter with a smooth midrange game who can shoot and facilitate would figure to draw plenty of interest on the open market—provided, of course, Nowell can reward Finch’s confidence by maintaining his per-minute production in an elevated role.