How Extension Season Signals NBA Trends

The August and September months are a slog for most NBA basketball fans, but they’re an important time for several important housekeeping items. Rosters are a key area of focus for front offices across the league, from possible cuts to training camp signees and guys on the bubble for the 15-man roster down the road. As Basketball Insiders’ Eric Pincus wrote recently, there are also a number of quietly important league deadlines looming around this time of year.

Most prominent among these is the rookie extension deadline of October 31, before which players entering their fourth year of a rookie-scale contract can negotiate with their incumbent teams regarding extensions that, if agreed upon, kick in to begin the 2017-18 season. If a player and team cannot reach an agreement before that Halloween date, the issue is effectively tabled and the player becomes a restricted free agent on July 1, 2017, with his incumbent team retaining matching rights on any outside offer sheet he signs.

The process is simple enough, but there are numerous variables at play that often make the execution a more complex affair. Teams can offer extra incentives to their very best players to keep them in town, which is why it’s extremely rare for a star-level player to change teams after his rookie deal, but many in the next tier down or below are playing a trickier game.

Locking a guy up before his final rookie-scale season keeps him completely away from the open market, a place where predatory competitors can tinker with poison-pill contracts that hurt a team’s position if they choose to match. Finalizing a deal early also offers the potential for a bargain contract if the player in question takes an unexpected leap in his fourth season.

On the other side of the coin, though, agreeing to a deal commits a team salary-wise regardless of the results in that fourth year. For deals signed with future development as part of the expectation, the risk of a bad contract down the line comes with the territory. Even if the superstars almost never go this route, a number of very talented guys have passed the deadline and hit restricted free agency in recent years.

Made up primarily of picks from the 2013 draft, the crop of extension-eligible players this fall represents a few distinct stylistic groupings: Rudy Gobert and Steven Adams highlight a strong group of “traditional” big men; Dennis Schroder and Michael Carter-Williams are two of several notable guards with numerous complementary skills but lack consistent jump-shooting; Kentavious Caldwell-Pope and Otto Porter are among a number of emerging “3-and-D” specialists looking to cash in on the modern value of their role; and of course, as will be the case his whole career, Giannis Antetokounmpo gets his own special category.

Not all these players will receive deals before Halloween, and what’s signed – or not signed – could tell us a lot about how the league values these types of players as the NBA’s next crop of young talent move into their primes.

The Treetops

Primaries: Rudy Gobert, Steven Adams, Nerlens Noel, Gorgui Dieng, Mason Plumlee

Even the grandmothers of discerning hoops fans know the league is trending smaller, but several notable names are set to test that trend over the next couple months. Elite defense is still easiest with a dominant big guy manning the paint, and the best of them do enough other things to be among the most valuable commodities in the game despite a lack of shooting prowess.

Gobert and Adams are the headliners this fall, both undisputed defensive anchors who double as rim-running pick-and-roll threats on the other end of the floor. It’s tough to separate bouts of apparent stagnation from injury concerns after a stop-and-go third season where Gobert missed 21 games and couldn’t ever really find his rhythm. However, he’s cemented his reputation as one of the premier interior defenders in the game, with a few underappreciated supplementary skills to boot. Gobert could be nearly done developing at 24 years old, though – something the casual observer perhaps doesn’t consciously realize.

How the Utah Jazz will approach his situation will be telling, and could reflect a lesson learned a few years back. A difference of a few million dollars reportedly kept them from locking up Gordon Hayward in the summer of 2013, causing Utah to lose a year of Hayward’s services on the deal they eventually matched from the Charlotte Hornets. At the same time, Gobert’s extremely low cap hold next summer could leave open a big chunk of flexibility for additional upgrades – if the Frenchman is willing to play ball and voluntarily table his extension talks until mid-July, with the understanding that he wouldn’t ink a potentially harmful deal elsewhere in the meantime.

That’s a lot of risk, though. As noted by Dan Clayton on the latest Basketball Insiders podcast, that space under the cap the Jazz could conceivably save if they tabled Gobert’s talks might be significantly lessened or even eliminated anyway if the Jazz look to restructure Derrick Favors’ contract – something that makes so much sense that it’s been discussed by local outlets and our Eric Pincus for months. If that happens, a Gobert extension feels even more likely before the deadline.

There’s a similar calculus for Adams in Oklahoma City, where Sam Presti and crew have been silent to this point on extension talks for not only the big Kiwi, but also Victor Oladipo and Andre Roberson. Presti has typically acted early in these scenarios, and there’s a real chance the Thunder are playing the longer game here and hoping for trust – particularly from Adams.

After losing a ton of talent in Kevin Durant this summer, holding off on extensions and saving the cap space will allow OKC to take a real run at the free-agent market in their last chance to re-stock before Russell Westbrook hits unrestricted free agency in 2018. Adams might be the exception, especially if he’s willing to take a slight discount on his near-max value in exchange for security, but even in his case – and even with the understanding that he’s a core piece staying in Oklahoma City no matter what – a deal before the October 31 deadline seems like no sure thing.

For guys like Noel, Dieng and Plumlee, the final dollar figure is likely more interesting than the timing. Team roster situations could play a big role: Noel suddenly finds himself in a frontcourt cluster with multiple other lottery picks including No. 1 pick Ben Simmons, while Plumlee just watched seemingly every teammate (plus a new center in Festus Ezeli) get a huge raise and clog up Portland’s books ahead of his big extension summer. Dieng is the only one of the three with a relatively safe role, but it’s tough to gauge his value (and whether he’s worth locking up ahead of his fourth season) in a situation where he isn’t even the fourth-most valued young player on an up-and-coming team.

The way these guys are approached by their incumbent teams will be dictated in part by circumstance, but they could tell us something more. Are younger teams willing to pony up for big man talent even if it risks future flexibility, or will they test the perils of restricted free agency in hopes of finding more modern talent and (hopefully) still retaining their big later on?

No-J Handlers

Primaries: Dennis Schroder, Michael Carter-Williams, Victor Oladipo

An even smaller niche as the league modernizes is the talented ball-handler who does many things well but can’t shoot an accurate enough jumper, and several notable candidates for extensions dot the pool in this category as well.

Oladipo may fall into a similar category as Adams in Oklahoma City. With a huge summer already on the horizon next year, it’s tough to imagine Presti and Co. committing a big number to a guy who hasn’t even played a game in a Thunder uniform yet. Carter-Williams feels like even more of a lock to enter the 2016-17 season without an extension, especially considering the Bucks just brought in Matthew Dellavedova at the same position. And even if there’s money left for Carter-Williams after Antetokounmpo gets his expected max raise, it’s unlikely John Hammond and his brain trust will want to shell it out before seeing how things fit on the floor.

Schroder probably falls between those two skill-wise, but he’s a completely different ballgame. The Hawks signaled his inheritance of their starting point guard position when they traded away Jeff Teague before the draft; letting Schroder enter his final rookie-scale year without an extension in place would appear to run completely contrary to this line of thinking.

That doesn’t mean it’s a sure thing, of course. Schroder and his representation surely recognize this same reality, and could be pushing for a big payday. Will they be willing to play the game of chicken and refuse a fair market extension, demanding more or allowing Schroder to prove his own value as a starter? Like always, it’s a big risk – a career 32 percent three-point shooter at the point has a ceiling, and Schroder probably isn’t upping his current value next year unless that sees a real uptick. There would appear to be motivation on both sides to get a deal done before October 31.

These types are a dying breed in the NBA, and their eventual market could reflect that. Teams might be more willing to let restricted free agency dictate their value; in return for security, these players and their agents might become amenable to accepting less than what they feel they’re worth. What we hear and see on these names in the next couple months will be telling.

3-and-D Specialists

Primaries: Otto Porter, Kentavious Caldwell-Pope, Andre Roberson

Where traditional centers and non-shooting guards could have a plethora of talents but be left behind for lacking one or two vital skills, “3-and-D” wings are completely at the other end of the spectrum: Even if they’re pretty limited in many aspects of the game, the value of these kinds of players is exploding if both “3” and “D” are present in their skill set. Kent Bazemore, an athletic but limited swingman who does pretty little outside shooting threes and defending multiple spots on the perimeter, got a payday the same size as Dwight Howard this summer.

Exactly how far this concept can stretch will be tested by this extension season, and Porter might be the perfect case. At 23 and sporting a career 35 percent mark from deep, Porter barely qualifies in one half of the equation; many in Washington will tell you it’s a coin flip for the “D” part on a given night as well. Metrics may disagree on the latter half – ESPN’s Defensive Real Plus-Minus placed Porter in the upper tier of defenders at the small forward spot, and others have similar outputs. In either case, Porter isn’t doing a whole lot else on the court.

With the other two members of Washington’s starting perimeter eating up a combined $40 million or more every year moving forward (and reportedly feuding to some extent), whether these glue skills alone are enough to break out the checkbook yet again for Porter is an intriguing question. Porter and his representation know full well the value the league places on his primary functions, and could easily be willing to risk injury or slight regression to let him hit the market next summer if the Wizards are reticent to commit so much money to three guys.

It feels like a more tightly-run ship in Detroit currently, but that doesn’t make Caldwell-Pope’s impending extension eligibility any less complex. Barring a sizable salary-shedding move before July, a deal with KCP this fall would immediately stamp out any cap space the Pistons may have been hoping to use on the free agent market in 2017. If Stan Van Gundy is going to act now, it’s with a virtual certainty that this is his group for the future.

Van Gundy is a savvy executive, though. He already curried favor among his players by rewarding Andre Drummond with a deserved five-year max after Drummond did the franchise a solid and waited on his own rookie extension, allowing the Pistons to sign additional pieces alongside him. It’s tougher with a non-max guy like KCP, but look for the same approach here; Van Gundy can sell team loyalty after a successful 2016 summer, and might even be able to kill two birds by adding more talent next offseason before once again rewarding one of his guys for their patience. There’s still a lot of risk here though, and Caldwell-Pope’s agent, Rich Paul, is known for hard-nosed bargaining.

Further still, this is a distinct seller’s market. There are fewer capable “3-and-D” guys in the league than there are needs for such players. The summer of 2017 will introduce even more money into the equation, and guys like Porter and Caldwell-Pope simply have to look back at the contracts signed in the past few months to see what they might be in for. Their team situations could determine outcomes this fall, but just how far the league’s obsession with these two skills stretches will be interesting to track through next offseason.