Long after the NBA negotiated salary limits for first-round picks, teams still have to make enormous decisions about very young players who somehow continue to feel like NBA unknowns. Big-money extensions for guys entering their fourth seasons — the kind of deals we’ve already seen for John Wall and LARRY SANDERS! — present the most challenging such dilemma, as teams weigh a pile of unpredictable variables before deciding between a long-term contract and the relative control of restricted free agency.

But another thorny decision comes years earlier: whether to pick up third-year and fourth-year team options for first-round picks. Those fourth-year options can be especially pricey, since the collective bargaining agreement mandates massive raises between Year 3 and Year 4 in a player’s career; had the Blazers kept Nolan Smith for the full four years of his contract, he would have received a $58,800 raise in his third season and an $844,000 raise the next season. The Blazers cut bait early, declining Smith’s third-year option — a rare extra-early snub only about two players per draft suffer.

Higher-ups are speculating that teams may become more choosy picking up pricey fourth-year options under a new CBA that carries harsher penalties for big spenders. There is some evidence that may be happening already. Teams have to make the Year 4 call before seeing the player log a single second in his third NBA season — in other words, after only two seasons.

The new CBA has teams acting more carefully in preserving long-term flexibility. Will that trickle into upcoming decisions on Year 4 options, with the October 31 deadline to exercise them now less than two months away? Here’s a look at six of the most uncertain eligible players, with a brief take on their respective games and some league-wide intel on their contractual futures.

The Great Unknown

Derrick Williams, Minnesota Timberwolves

There are higher-profile sources of intrigue — DeMarcus Cousins, for one — but I’m not sure any player is generating the same churn of curiosity, confusion, and opportunism around the league. As the no. 2 pick in the 2011 draft, Williams would earn a monster $6.3 million under the terms of his fourth-year option — a $1.3 million raise over his salary for the coming season, and potentially enough to make the difference between the Wolves having easy access to the full midlevel exception or butting past the luxury tax.

And nobody, not even the Wolves, has any clue what position Williams should play. David Kahn, the deposed Minnesota GM, drafted Williams in hopes he could transition to small forward next to Kevin Love and Nikola Pekovic. But the lockout robbed Williams of any training camp or real practice time before his rookie year, and Love’s injury issues last season forced the Wolves to play Williams almost exclusively at power forward.

“One of the two toughest transitions for anyone to make is going from power forward in college to small forward in the NBA,” says Flip Saunders, Minnesota’s president of basketball operations. “Derrick’s only 21. But he has to carve out an identity for himself. That’s the most important thing for him.”

Williams has shown some potential as a small-ball power forward — a spot-up shooter who could stretch the floor around pick-and-rolls for Love and Pekovic. Williams has been a disappointing shooter so far in the pros, but he hit an almost-respectable 33 percent from deep last season, he has a nice stroke, and guys who shot as well as he did from deep in college have almost universally settled in as above-average 3-point shooters in the NBA.

Saunders says Williams could turn into something like a more athletic Al Harrington, spotting up on the weak side of pick-and-rolls — as he does here on the left wing, opposite a Ricky Rubio–Pekovic two-man play:

Having Williams do this at power forward drags an opposing big man out of the lane and presents Williams with an easier decision tree if he catches the ball: shoot, pass, or drive. Williams has struggled badly to make choices in even more crowded situations closer to the rim. He’s a bit of a ball-stopper, out of greed and decision paralysis — both no-nos in Rick Adelman’s corner offense. Way too many Minnesota possessions ended with Williams catching the ball after one action, holding it 20 feet from the hoop with a dozen or more ticks left on the shot clock, and then engaging in some very sad series of jab steps and crossover dribbles before launching a horrific step-back jumper. Watching Adelman’s reactions to these shots became the game-within-a-game for League Pass addicts and/or folks who enjoy coaches acting out their misery in hilariously grandiose pouty gestures.

“He has to make better decisions,” Saunders says. “And he has to make quicker decisions.”

Williams has struggled to create anything in Adelman’s system. He’ll occasionally blow by overmatched power forwards on dribble drives and break out a crafty finish, but it’s unclear if he can do that against small forwards, and he’s flirting with very bad territory as a non-passer. He dished only 84 assists combined in two seasons, and last season, Williams became only the 12th player in the 3-point era to assist on fewer than 5 percent of his team’s buckets while using up at least 23 percent of Minnesota’s possessions with a shot, turnover, or drawn foul. Most players in this group are low-post finishers; Eddy Curry and Amar’e Stoudemire alone account for seven of the 19 player seasons on the list.

Williams is not a low-post finisher, and we’ve seen almost zero evidence he can work as an effective outside-in creator. There’s nothing wrong with being a stretch power forward off the bench; Harrington became a very effective one in Denver once he learned to either shoot open 3s or drive hard to the rim — and to make the choice right away, decisively.

The downside of playing Williams at power forward: He’s too small, at 6-foot-8 with a 7-1 wingspan, to defend the rim. Williams isn’t really a bad defender; he understands team schemes and help responsibilities, and he’s shown good balance in being able to rush out a shooter, stop on a dime if that shooter pump-fakes, and stay shoulder-to-shoulder with that shooter on a drive to the rim. But he has no shot in the post against the league’s back-to-the-basket behemoths, and he provides zero deterrent as a help defender at the basket.

These problems aren’t as serious if Williams settles into a role as a heavy-minutes backup power forward, spotting up and defending less threatening backups. But that’s not the ideal outcome for a no. 2 pick, and it might not be worth $6.3 million to Minnesota. Saunders wouldn’t comment on Minnesota’s plans for Williams’s fourth year, but he knows teams are eyeing Williams as a potential buy-low trade candidate.

Big-Money Busts?

Jimmer Fredette, Sacramento Kings

The Jimmer would earn $3.1 million under the terms of his Year 4 option, and you can get better players for that kind of money. Mike Malone, the team’s new head coach, put the kibosh on the whole “Jimmer is a point guard!” thing over the weekend by excluding him from Malone’s personal list of point guards on the roster.

Everyone knows Fredette’s issues on defense. The Kings have to hide him on either a punchless (and hopefully undersize) wing player, and if that option is unavailable, pray the opposing point guard is among the league’s least threatening. But even non-threats become dangerous against the most glaring defensive liabilities. Bigger shooting guards without much off-the-dribble panache — think Danny Green or Thabo Sefolosha — can see the rim better over diminutive Jimmer, and point guards without night-to-night post-up games can fulfill their fantasies in the paint against him. Waterbug point guards know they can leave Jimmer in the dust on pick-and-rolls; he gets hung up badly on screens, and lacks the start-and-stop speed to catch up:

But the man can shoot, and teams need shooting more than ever against defenses that overload the strong side and focus on taking away a team’s best options. Jimmer works best as an off-ball shooter, but playing the passive spot-up role requires someone else to play point guard, and most Jimmer–point guard combinations will be borderline unplayable defensively.

But Jimmer can handle the ball fairly well. Defenders have to go over screens against him in the pick-and-roll, presenting Jimmer with the shot that will keep him relevant: the off-the-dribble 3-pointer in situations like this:

The key might be what else he can do with the ball, especially when defenses take away that off-the-bounce triple. Big men guarding screeners step beyond their comfort zones to combat Jimmer’s shooting, just as they do against Stephen Curry, and Jimmer can take advantage by turning the corner on them or splitting traps:

He’s been able to get into the lane now and then for floaters or drop-off passes to big men lurking along the baseline.

The flip side: When a pick-and-roll doesn’t produce an easy opening, either via shaky help defense or a rock-solid screen that nails Jimmer’s guy, he doesn’t have the jets to produce much of value. Defenders can stay with him and block off the lane, resulting in very tough leaners and step-back jumpers. He has few weapons with which he can puncture the heart of a defense. If Jimmer can bag the ultra-tough misses and focus on the good, he’s got a role in the league. But given his massive disadvantage on defense, it’s probably not a role that should ever pay $3.1 million.

That price matters to Sacto. The Kings aren’t actually slated to have any cap room next summer once you factor in cap holds for Cousins, Greivis Vasquez, and Patrick Patterson, and even if you assume they renounce the latter two and buy out John Salmons, they’ll still come in only about $5 million under the projected cap.

Other teams are circling, curious whether they can land the heralded Jimmer for a song — a no-harm, no-foul gamble. Will the Kings bite?

Bismack Biyombo, Charlotte Bobcats

Biyombo isn’t worth nearly the $3.87 million salary he’s slated to earn in Year 4, an $800,000-plus raise from his third-year salary. Nobody knows exactly how old he is, and there’s not much place in the league for bigs who can’t do anything with the ball, can’t shoot free throws, and rebound at merely average rates — especially if said big men aren’t “A”-level defenders.

And Biyombo, drafted as a stopper, is not close to that level. He’s still got high-upside athleticism, and he can protect the rim, but he hasn’t been able to translate that into effectively tracking multiple opponent actions over a full shot clock. It’s almost as if Biyombo gets mentally fatigued dealing with all the responsibilities that come with anchoring a defense. He’ll bump the first cutter or corral the first pick-and-roll with startling alertness, only to blow the second pick-and-roll or miss the next cutter coming from the weak side. You can find a lot of sequences like this one, in which Biyombo (guarding Roy Hibbert in the middle) is unaware, head turned the wrong way, that a double-team has left an opposing player (Paul George, along the left baseline) wide open to catch the ball and lay it in before Biyombo can respond:

Charlotte’s helter-skelter schemes under Mike Dunlap didn’t help, and Biyombo’s job should be a bit easier this season under Steve Clifford. The coaches and front office will be watching. “I’ve told him this, but he has to build his game around being a better rebounder and defender,” Clifford says. “That will give him a chance.”

“For him to get consistent minutes, he needs to rebound,” says Rod Higgins, Charlotte’s president of basketball operations. “He’s going to have to become a better team defender.”

Being a good defender is nice, but if Biyombo doesn’t develop on the other end, he’s on the way to becoming a glorified Joel Anthony. If you watched only what Biyombo does before catching the ball, you might have some hope. He sets a nice pick, he runs the floor like hell, and he’s flashed some deft footwork on the pick-and-roll.

But once Biyombo gets the ball? Yeesh. If he has to dribble it, he’s toast. And even if he doesn’t, he essentially has one move: dunking the ball. When he’s too far away for a dunk, Biyombo just sort of jumps, holds the ball up with one hand, and hangs in the air until he has to release the thing over a defender. It looks like a jump hook, but it’s really just a dunk modified for distance.

Still, there is some interesting raw material here. Smart teams with sound cultures might kick the tires on a low-ball trade offer, and the Bobcats are set to be far enough under the cap that they might pick up Biyombo’s option anyway.

Jan Vesely, Washington Wizards

Vesely attempted 65 shots out of the pick-and-roll and via generalized “cuts” last season, per Synergy Sports. I watched all of them. He made 30. Five were air balls, and exactly zero were jump shots that went in the basket. Steve Buckhantz, the Wizards’ play-by-play announcer and perhaps the TV guy least able to hide his ongoing misery, reaches new levels of depression calling Vesely shots:

Buckhantz as Vesely leaps to shoot:

“Jump hook …”

[Long pause as the shot rises.]

[Shot is an air ball.]

[Two more seconds of silence as play continues.]

Buckhantz, sighing: “Misses everything,” followed by hysterical crying.

Vesely made 12 free throws all season. He’s a clever passer out of the pick-and-roll when he catches the ball rolling into traffic, but that cleverness stems in part from his urgent desire TO GET THE FUCKING BALL OUT OF MY HANDS BEFORE SOMEONE FOULS ME AND THE CROWD STARTS BEING MEAN AGAIN. When Vesely catches and shoots in traffic, the attempts aren’t shots as much as “flings” — one-handed layups, ball extended far from body, launched while Vesely is almost half-blind from the basket and before anyone can converge on him. Needless to say, this is not a good way to score baskets or get to the line. The one exception: When he catches the ball in space on the right side of the floor, he’s shown a nifty one-dribble move into a softy lefty runner. But even that is a tough, tough shot.

Head coach Randy Wittman’s playbook includes a half-dozen sets designed to get Vesely an alley-oop dunk. Those are nice when they work, but they’re tough to choreograph against smart defenses, and they represent a form of surrender that basically indicates, “He can only dunk, but he can’t dribble or score through traffic, so let’s design some alley-oops.”

Look, it’s not like you can’t see what Ernie Grunfeld saw here. Vesely’s an athlete with good intentions, and he plays defense at times with a surprising nimbleness of both body and mind. But he’s prone to over-helping — you can sometimes hear teammates shouting for him to get back to his guy — and the man who once fouled out of a summer league game, when you get 10 fouls, actually fouled more often per minute in Year 2 than as a rookie. That’s troubling.

The Wiz are hopeful Vesely might earn more minutes with Wall and Nene. Wall helps any big man, and Nene’s passing and jump-shooting could give Vesely some space to breathe off the ball. But with Harrington in town, Vesely really will have to earn those minutes, Grunfeld says.

Washington has decent cap flexibility going forward, but Vesely’s $4.2 million Year 4 option for 2014-15 could take the Wiz out of max-level room territory. Even if the Wizards tried to move him, the market as of now would be cold.

The Sure Bets in Utah

Enes Kanter

Utah will exercise Year 4 options on both Kanter and Alec Burks. The Jazz have essentially no long-term commitments, meaning they can keep paying all four of their core young guys without any cap or tax worries — for now.

Kanter hasn’t done quite enough to justify a monster $5.7 million fourth-year option, but that’s due to playing time issues; Kanter didn’t play in college, and he’s been no. 4 in Utah’s big-man pecking order. He barely cracked 1,000 minutes last season, much fewer than we’d expect from a no. 3 selection working as a full-time rotation player on a .500 team.

Kanter loves to work from the left block, Al Jefferson’s undisputed territory. But Kanter already projects as a very effective scorer from there — the rare back-to-the-basket force who scores with both hands, demands double-teams, and shows a feathery shooting touch.

Kanter can overpower smaller defenders, and he’s flashed a variety of moves from the left block — a righty jump hook in the lane, an up-and-under counter that ends in a lefty layin, and a soft spinning baseline shot that vaguely evokes Hakeem Olajuwon (but which Kanter shoots too eagerly). Utah is still figuring out how to mix Kanter’s post-up game with Derrick Favors’s pick-and-roll basket dives, but they’ll have much more time to do so now that Jefferson and Paul Millsap are gone. And they’ve already tinkered with having Kanter duck in for a post-up on the left block as Favors pick and rolls down the lane — a simultaneous bullying attack Memphis has long used with Zach Randolph and Marc Gasol:

Kanter expanded his pick-and-roll game, showing some nice footwork in creating passing angles and an ability to catch in traffic and launch tricky floaters. But those are low-value shots, and Kanter now faces the challenge of progressing without a credible pick-and-roll point guard.

He also improved as a passer after somehow recording just eight — eight! — assists as a rookie. He can see the floor well on the move and from the post, and coach Tyrone Corbin even let Kanter handle the ball from the elbow now and then. Again, the nuances of big-man play come slowly.

Kanter’s already a monster offensive rebounder; only Reggie Evans and Hibbert snagged a higher percentage of their own teams’ misses last season. Watch Kanter after he whips a pass from the post to an open shooter. He’ll spin to inside rebounding position before that shooter even releases the ball.

Kanter’s ceiling as a defender probably isn’t very high, and it’s certainly lower than Favors’s. Kanter isn’t especially fast or athletic (as a leaper, at least), and his wingspan is relatively short for someone his height. But topping out as “solid” would be fine, given his potential on offense. Kanter tries hard on defense, to the point that it almost looks as if his feet are always moving — sort of like Luigi jumping in Super Mario Bros. 2. The happy feet can make it hard for Kanter to maintain full control of his body, and to shift his momentum smoothly from one direction to the other; point guards who are clever changing directions around the same screen on a pick-and-roll can leave Kanter in the dust. And sometimes, it took only a crossover dribble — especially when Utah had Kanter chase point guards far from the rim:

But he’s young, he cares, and he’s a decent athlete. He’ll be fine.

Alec Burks

This would be more interesting if the Jazz had any cap issues, and even now, Burks generates a lot of interest in spitballing sessions with team execs outside Utah. He’s the Jazz’s fourth banana, he’s set to earn a fat $3 million on his fourth-year option, his PER declined badly last season, and teams have long wondered whether the opaque Jazz might be willing to deal him.

Burks has the toolbox of a nice rotation cog. He’s got the size and wingspan of a shooting guard, and enough ball-handling chops to work as a secondary pick-and-roll guy. He also shot 35.9 percent from deep last season — exactly league-average, encouraging for a second-year guy who enjoys adventurous shots.

But there’s a big gap between “decent rotation cog off the bench” and “above-average NBA starting guard,” and Burks has to rejigger his decision-making in order to end up on the happier part of that continuum — and/or become the kind of 3-point shooter that defenses actively respect.

An emblematic tic: Burks dribbled away from the pick on 36 percent of pick-and-rolls he ran, the highest such rate by a giant margin among guys who ran at least 35 pick-and-rolls, according to Synergy. Going against picks isn’t bad by definition. It’s a way to catch a defense leaning the wrong way, and Burks’s explosiveness driving with his weak (left) hand is a huge asset.

But any habit becomes damaging when defenses can plan for it and use against you. This is especially true on side pick-and-rolls, a play Utah often called for Burks. Defenses on such plays typically try to force ball-handlers away from the screen and into a triangle of death formed by the sideline, the baseline, and the big man defending the screener. They regularly trapped Burks within that triangle, and Burks usually responded by launching bad off-the-bounce jumpers. Here’s Burks on a rejected pick-and-roll with Jefferson on the right wing:

And here’s the scene just before a Burks-Kanter rejected pick-and-roll leads to a long miss against San Antonio:

These are low-efficiency on their own, and even more so when you factor in the missed opportunities of Burks driving-and-kicking or resetting the offense. Burks’s love of shooting is one reason he assisted on just 13 percent of Utah’s baskets while on the floor, one of the lowest marks in the league for a guard. Burks’s assist numbers might jump without Jefferson and Millsap around to act as inside-out cogs, but Jefferson’s departure also means Burks won’t get the same kind of open standstill 3s as a result of Big Al drawing double-teams.

Burks is a little jumpy on defense, and he’ll be late on perimeter rotations here and there. But most young players fight through similar issues learning the roving nuances of NBA defense. Burks should be a reliable defender in the long run, and Utah is a cinch to pick up his fourth-year option. Even if Burks’s ceiling ends up as an off-the-bench combo guard, that’s a decent outcome for the no. 12 draft slot, and currently an easy choice for Utah.

But some of the other cases on this list are thornier, and an option pickup doesn’t signal the end of the story — especially not for these six guys.