The Big Questions Heading Into Free Agency

Being an informed modern fan of the NBA involves cultivating an understanding of (and opinions on) two interrelated but fundamentally distinct facets of the league. The first is the game of NBA basketball as it takes place on the floor. The second, which a great many fans pay more attention to than the games themselves, is the business of team-building. With the games concluded, the championship decided, and the draft in the rear view, it is now time for the business of the league to come to the forefront. The landscape has already been altered dramatically over the last two-plus weeks — injuries to KD and Klay Thompson, the Raptors’ first title, the Anthony Davis trade, and Zion being drafted — but these changes may pale in comparison to the seismic shifts we are about to see over the next several days. Before the wild spending spree begins, let’s discuss some of the key questions which will shape the free agency period, starting with the big picture.

Have teams learned the lessons of 2016? The historic cap spike of 2016, largely driven by the NBA’s massive new TV deal, had front offices falling all over themselves to light cap space on fire, often to disastrous effect. The spike shaped the league’s on-court reality — it gave Golden State the necessary cap room to sign Durant, for one — but it also locked a number of teams into grim financial situations for which the only remedy was time.

Well, time has passed. Most of the egregious deals handed out during the orgiastic summer of 2016 have either run out or are set to expire in 2020. After the two resulting summers of relative austerity in 2017 and 2018, there is once again a glut of cap space around the league. Based on the projected cap figure of $109 million for ’19-’20, teams have an estimated $474 million in cap space to dole out, which doesn’t even account for the amount they will spend over the cap to retain their own free agents via Bird Rights.

Logic would dictate teams will remember the pain from getting locked into cap-crippling long-term deals in 2016 and adjust course, but if we’ve learned anything over the years, it’s that this is NOT a logical league. The conditions on the ground could also exacerbate the temptation to get silly once again. With Golden State falling from its perch atop the league and all the roster shakeups set to happen (a full 40 percent of the league’s players become free agents at 6 PM ET Sunday), a larger-than-normal number of franchises may conclude they are only a move or two away from becoming the next Toronto and overspend accordingly to try to make it happen. The Lakers and Jazz already made their all-in moves with the AD and Mike Conley trades, respectively. They may not be done, and a number of other challengers to the throne will soon emerge as well.

Realistically, there were always going to be enough “haves” at the top of the market to take the big names off the board, but whether or not the spending again rises to the level of Greek tragedy depends on the teams at the other end of the spectrum. The error in judgment which drove a lot of the reckless spending in 2016 came from teams who misunderstood their position within the league hierarchy and competitive cycle. These squads (cough, Lakers, cough), unable to land the marquee free agents, instead overpaid for players they sold to their fans as the missing piece(s), when in fact they were mostly just roster flotsam clogging up their cap and preventing them from making better moves to return to contention. [To wit: the cap penalty for Luol Deng, waived via the stretch provision after the disastrous 4-year/$72M contract they handed him in 2016, is now the longest-tenured Laker, and will still be clogging their cap sheet and making it more difficult to fortify their pencil-thin roster all the way through 2022. Brutal.]

In 2019, with the power of hindsight, will these teams in the middle and bottom of the league realize they shouldn’t blow their cap space just because they can? Will they hesitate in giving out long-term deals to maintain future flexibility in trades and free agency? Or will all that sweet, sweet cap space burn holes in their pockets once again? If nothing else, it’s probably safe to assume the Timofey Mozgovs and Ian Mahinmis of the world won’t get $64 million deals this time around. The league just has a better sense of what types of players it values now, and they ain’t it, chief. But once we hit around July 5th and all the big names have been scooped up, don’t be surprised if shit starts to go haywire again. [Seriously, when you see the notification come across your phone saying Terrence Ross got like $55 million, remember we had this talk.]

Does anyone have a chance at Kawhi besides the Raptors and Clippers? The short answer is “probably not.” The Lakers maintain they will pursue the Finals MVP, but their path to max cap space remains somewhere between “murky” and “no fucking way,” and there is no reason to suspect Kawhi, at the absolute apex of his value, will have any interest in accepting either a financial discount or a secondary/tertiary role. Both New York teams have ample cap space and Brooklyn at least has an intriguing basketball situation (lol Knicks), but the lure of the Big Apple doesn’t appear to be all that enticing to Kawhi. As inscrutable as he is about most everything, the one consistent thing we know about him is his affection for his native Southern California and his desire to play there at some point. The Clippers’ pitch centers around a well-run organization in the city he wants to live — the Lakers can only offer him one of those two things — and a balanced roster just screaming for a unifying superstar to slot everyone into his proper role. Adding Kawhi (along with retaining useful free agents Pat Beverley and Ivica Zubac, ideally) and doing nothing else instantly transforms the Clips from playoff cannon fodder to serious contender. Beyond that, if they could find a taker for the final year of Danilo Gallinari’s contract (which probably wouldn’t be too difficult; he’s excellent when healthy and they have plenty of assets to attach as sweeteners), they have a reasonable path to another max slot. [Media reports have linked them to Al Horford, a pairing which would be an absolute nightmare defensively. The other alternative would be to load up on big wings, throwing offers at any one of Jimmy Butler, erstwhile Clipper Tobias Harris, or Khris Middleton. They could be really scary next year if things break right.]

Of course, all of the L.A. speculation relies on Kawhi deciding the grass is greener there, which is a somewhat difficult argument to make when the yard he’s currently inhabiting has the Larry O’Brien trophy sitting in the middle of it. It’s important to remember that NO reigning Finals MVP has ever switched teams in the history of the league. [FWIW, MJ retired in ’98 after the Bulls won their sixth title, so I’m mincing words a bit here. Whatever. It’s my column.] I’m not saying this necessarily matters to Kawhi or informs his legacy in any way, but it’s a useful piece of context. Toronto (and Canada as a whole) has done everything it can do to prove they will put Kawhi in the best possible position to succeed, and they can offer him an extra year and some additional dollars as a kicker. [He would max out at 5 years and approximately $190 million with Toronto, vs. 4-years/$140 million anywhere else.] The other option would be for Kawhi to opt for a LeBron/Durant-style “one-and-one” deal (essentially a two-year deal where the second year is a player option), but as I’ve written previously, he may be justifiably hesitant to go this route after witnessing first-hand what happened to KD, and how it has cast uncertainty onto the entire trajectory of his career. There is value in certainty and stability, even if the world is his oyster at this specific moment. [The counter to this argument is that all indications are KD is still going to get a max deal despite the catastrophic injury. So the risks may be mitigated when you’re a two-time Finals MVP and one of the very best players in the world.]

I can’t pretend to know Kawhi’s thought process (which seems to be the way he likes it), but he’ll be a national hero in Canada forever no matter what he does, so he may see this as a golden opportunity to exercise control over his own destiny and make his way to his desired location without having to suffer any of the Durant-esque P.R. bullshit. For most of the all-time greats, “free” agency is anything but, so it’s a rare thing to be afforded this chance. Political capital can’t sit in a bank, collecting interest; you either spend it or squander it.

Will the second- and third-tier stars take the cash or the chance at a fresh start? The top tier of free agents, in spite of all that’s happened recently, remains Kawhi, KD, and Kyrie Irving. Their decisions will likely be the first big dominoes to fall and provide a framework for the rest of the signings to follow. Next will come the complementary stars, the guys teams won’t want to build around but may see as the final pieces in their championship puzzles: Jimmy Butler, Kemba Walker, Al Horford, Tobias Harris, Khris Middleton, Nikola Vucevic, and D’Angelo Russell (who is restricted but would likely be available if Kyrie signs with Brooklyn). Based on how loose teams could get with their cap space, all of these players may be in line for max deals (or close to it), even if none of them are exactly no-brainers. Chances are their incumbent teams are prepared to back up the Brink’s truck (with the possible exceptions of Horford and Russell, because Kyrie), and the answer won’t be the same for everyone, but we’re about to collect a lot of data about what matters more to the modern NBA star: cash and continuity or true professional agency.

Kemba will be the most compelling test case here. Since he’s eligible for the supermax extension with Charlotte, he would be leaving over $80 million on the table to go elsewhere for a chance at a title. It would seem crazy to most of us, but at a certain point, the sums of money are all so large it kind of ceases to matter, an unintended consequence the NBA may have to wrestle with in its next round of CBA negotiations. It’s basically Dave Chappelle explaining the difference between $10 million and $50 million, only with even more abstractly massive dollar figures:

Most of the media chatter suggests Middleton will stay with the Bucks on a 5-year max deal ($190 million) or something in the neighborhood. [Yes, this is probably a gigantic overpay, but Milwaukee doesn’t have much choice. They have no means of replacing his production, and if it takes dipping into the luxury tax to both keep a championship roster together and appease Giannis — now the MVP of the freaking league, as you may recall some incredibly prescient and attractive analyst predicting way back in the preseason — long-term, then so be it.] The Celtics have been linked to both Walker and Vucevic, though they would only have the cap space for one or the other. Where Horford goes will be fascinating; he truly could be the missing piece for a contender, and rumors are he will command something in the range of four years/$112 million. [Big Al would be 16 seasons deep by the conclusion of said contract, so even someone as “safe” as Horford carries some risk.]

With so much cap space floating around, someone will certainly throw a max offer at Butler, even if Philly hesitates to do so. Rumors are swirling connecting Jimmy Buckets to Houston, an arrangement which would require a sign-and-trade similar to what they pulled with Chris Paul two summers ago. I already discussed both Butler and Harris as it pertains to the Clippers and their pursuit of Kawhi, but chances are both guys will have a number of suitors, and with J.J. Redick also being an unrestricted free agent, there is a doomsday scenario where the Sixers burned all of their assets and are left with nothing but Joel Embiid and Ben Simmons. Very little is certain this summer, but we can be sure it’s sphincter-clenching time in Philadelphia.

How teams value Vucevic will also tell us a lot about the free agent market and the state of the league. Word on the street is the 28-year-old Vooch will settle in around the 4-year/$100 million mark. Orlando has sworn up and down throughout the process they intend to retain Vucevic, who extended his range out to the three-point line this season and subsequently earned his first All-Star nod. However, the Magic already have a ton of resources dedicated to their front court, with Mo Bamba, Jonathan Isaac, Aaron Gordon, and newly-drafted Chuma Okeke in the fold. The decision on whether or not to throw a big offer Vooch’s way (and whether or not he accepts it) represents a major fork in the road for a franchise which finally began to emerge from the NBA’s untouchable class last season, in large part thanks to the play of Vucevic himself.

Even so, it’s fair to ask what the ceiling is for a team with him as the centerpiece (or one of them). He’ll be just shy of 33 by the end of the deal, and even though this newfound shooting stroke gives him a ton of value at the 5, he’s never been a particularly stout defender. If the solution is to essentially alternate Vooch and Bamba for offense and defense, respectively, that’s not a viable long-term approach. Throw in the way his presence could hamstring the development of the aforementioned young bigs, and the Magic, in ways they would never admit publicly, have to be seriously asking themselves if the juice is worth the squeeze. Perhaps if Isaac develops into a versatile, Giannis-like defensive presence at the 4, then there’s a road map to a workable front line pairing with Vooch, but that sure seems like it’s a long ways off, and the time to get maximum value from Vucevic is now. The night has been dark and full of terrors for Orlando, but even with day seemingly breaking, there are still no easy answers for them.

With Mike Conley being traded to Utah, the number of potential suitors for D’Angelo Russell’s services diminished by one. Indiana has been floated as a possible destination, but they seem locked in on Ricky Rubio, for whatever reason. Minnesota and Dallas are both possibilities, but let’s be honest here. Chances are, DLo is going to end up in the one location that will have us all shaking our heads when we hear the news: the Los Angeles Lakers. Nothing would be more quintessentially Lakers than giving away a talented, young player as a means to create cap space, only to later use their cap space to sign the exact same player, except now they’ve lucked into a better, more mature version of him after Brooklyn did the heavy lifting of developing him into an All-Star. It would be the ultimate endpoint of the “bad process, good result” M.O. which permeates their entire organization in the post-Jerry Buss era. Plus, for all of GM Rob Pelinka’s bungling of their cap space as a result of the AD trade, Russell’s max deal would inherently come in at a lower salary figure than would a deal for an older star, so the pathway to having enough space to sign Russell is much more linear than it would be for one of the Kawhi/Kemba/Kyrie types. Luck tattooed to their asses, I tell you.

[It would also be appropriate to include Klay Thompson in this section, though all signs point to Golden State eventually ponying up a five-year max offer to keep him in the Bay Area. Despite his ACL tear in the Finals, it would be insane for them not to pay that man his money.]

[One dark horse team to watch when it comes to these secondary stars is New Orleans. While it appears they are content to take the slow and steady approach to team-building around Zion, they have somewhere near max cap space right now and could easily pivot into “Hey, let’s contend right now because we still have a bazillion draft picks going forward so what’s the difference” mode if they so chose. How many games do they win next season if they were to add, say, Horford to what they already have? Fifty? I have no idea where this Pelicans thing is going over the next few years, but it’s going to be fucking wild.]

Which role players could turn out to be difference-makers? Time for the lightning round:

• Dewayne Dedmon: A guy who has mostly been trapped on garbage teams, he could be a really useful backup big/spot starter on a contender. He moves well on switches, defends the rim, and spaces the floor (38.2% from three on 3.4 attempts per game last season), while never clamoring for a bigger role. He may not be getting a lot of media attention, but the word is a number of teams are all over him.
• Thad Young: He’s a known commodity at age 31, but that commodity is really useful! Young, as he has always been, remains a versatile defender, a low-usage, low-mistake offensive Swiss Army knife, a solid veteran locker room presence, and a juuuust good enough outside shooter (34.9% from deep last year) to make defenses respect his gravity at the 4. Can he be the third option on a contender? Of course not. But as a team’s fifth-best guy? Rock solid. Utah feels like a natural fit for him.
• Richaun Holmes: Something of a personal crusade for me. I’ve just always liked this dude’s game, and I’ve never been able to figure out why a team won’t give him a consistent role. Holmes plays with a relentless energy and athleticism, and he’s a little more skilled than you would think. He can eat up minutes at both the 4 and 5, and he won’t cost much. Someone give this man a real shot!
• Taj Gibson: Yeah, I know there’s no real upside at this point with him. It just feels like he should still be playing meaningful playoff minutes for someone instead of staring in disbelief as another defensive breakdown by Towns or Wiggins leads to a layup. A “16-game guy” who could be had on the cheap.
• DeMarcus Cousins: This feels like cheating, of course, but what on Earth kind of deal is Boogie going to get this summer? There is simply no way for a team to know if they are going to get the borderline unplayable version of him from the Finals or something closer to his earlier All-Star form. Teams may read a bit too much into how his rehab year with Golden State went down and be scared off, and if no real market emerges yet again, he could turn out to be a steal.
• Jeremy Lamb: It feels like he’s been in the league forever, but Lamb is only 27, and he quietly had his best season as a pro last year in Charlotte. He has the length to be a switchable defender, hits catch-and-shoot threes at a solid rate, and has some juice as a secondary playmaker. Dudes who were written off too quickly early on in their careers and then begin to put it all together as they reach their primes tend to be good buy-low investments, and Lamb fits the bill here.
• Rondae Hollis-Jefferson: RHJ is perceived as something of a disappointment to this point in his career, but I believe this is in large part because he’s been misused. At 6’7″ and 217 lbs, Hollis-Jefferson has the body of a wing, but he’s really an undersized big man. He can’t shoot — AT ALL — but he’s still a tremendous athlete and a hellacious defender, and only 24 years old. He may never be a plus on offense, but if a team could pair him with another front court bench player who can shoot but perhaps has some deficiencies on defense, there may still be something there.
• Darren Collison: No flash, no frills, just a solid veteran. If the point guard carousel stops and Collison is left without a starting gig, he instantly becomes one of the most competent third guards in the league, a role for which he is probably better suited and could be had at something of a discount.

Which restricted free agents could teams be looking to poach? Putting in offers on other teams’ restricted free agents is risky business because in most cases, if the player is worthwhile, the offer will get matched, and it ties up the offering team’s cap space for those critical few days while the incumbent decides. That said, if a suitor is willing to overpay, they can sometimes hold the matching team’s feet to the fire and force them into a tough decision. We already discussed the politics surrounding D’Angelo Russell’s situation, but here are a few more RFAs teams may be sniffing around:

• Malcolm Brogdon, Milwaukee Bucks: What happens with Brogdon is going to be fascinating. He is clearly one of the league’s elite role players, and maybe Milwaukee will just swallow hard and pay whatever it takes to retain him. But boy, are they going to feel a financial pinch if they elect to keep all of Middleton, Brogdon, and Brook Lopez. It’s a virtual lock someone is going to throw out an offer sheet in the neighborhood of 4-years/$80 million for Brogdon, and we won’t have to wait long to get a definitive answer about how far Bucks’ ownership will go to keep a championship core around Giannis. Buckle up for this one.
• Tomas Satoransky, Washington Wizards: This may be a case of the other front offices smelling blood in the water. Sato, 27, has developed into a quality player. He’s an underrated playmaker with an advanced feel for the game. He has the length to guard multiple positions and has worked to become a solid spot-up shooter. He has assumed a number of different roles and been effective in all of them. Any number of teams could use his skill set. Remember, the Wiz still do not have a permanent GM in place, and they currently have about $65 million committed to their “starting” back court his year (quotation marks because $37.8 million of that is going to John Wall, who will not play in ’19-’20). They may be hesitant to throw more long-term money at another guard, even one who would prove useful in Wall’s stead this season. Indiana, Boston, Dallas, Orlando, and Miami could all be teams with some interest in Satoransky.
• Tyus Jones: I may be the last one still occupying Tyus Island, but I feel as though we’ve given up on him prematurely. He’s a bit undersized, and his shooting has yet to come around, but he’s still only 23 years old, and both the analytics and eye test show me a guy who is always making positive contributions to his team without sucking up much usage. There’s a place for that guy in the league, especially on a team with a ball-dominant wing or combo forward, and it doesn’t appear as though Minnesota is likely to value him too highly. Seems like a classic buy-low opportunity.
• Ivica Zubac: I suspect the Clippers’ sharp front office won’t be asleep at the wheel on this one and will match nearly any offer, but it only takes one asshole to do something crazy. Every time I watch this guy play, I am perplexed by how continually overlooked he is. Zubac is really good! His style is a bit retrograde in the modern game and he needs shooting around him to thrive, but he consistently does traditional big man things well and makes a positive contribution when he’s on the floor. He rarely shoots from beyond ten feet, but he’s also only 22 years old, so his game still has plenty of room to expand over time. A team in the lower echelon of the league could do a lot worse than using some of its mostly meaningless cap space on a guy like Zubac. If nothing else, a big offer sheet could force the Clippers into a more difficult financial position. Sometimes the gamesmanship is the point.
• Delon Wright: I’m tempted to just copy and paste most of the Satoransky section, but my loyal readers deserve better than that. Much like Sato, Wright is another long guard who knows what the hell he’s doing and could help a lot of teams if he weren’t trapped in a rebuild. Memphis may want to keep him around to act as the adult in the room for their ultra-promising core of young cubs, but a mentor role can only be worth so much, and I have to imagine they have a threshold number in mind.
• Terry Rozier: Again, what happens with Rozier will largely depend on how the Kyrie-Kemba-Russell game of musical chairs shakes out because there could be a scenario where the Celtics need him to be their starter next year. In any case, Boston may have soured on Scary Terry to a degree, as he spent much of the past unpleasant year grousing about his reduced role. Another team might see him as a starter and thus overlook this bright red flag, but with the glut of quality point guards in the league today (and how many of them are also free agents), who would that team be?
• Kristaps Porzingis: Just kidding. Cubes and Dallas will take good care of the Lativian Gangbanger.

Enjoy the absurdity everybody, and check back next week for a breakdown of all the insane piles of cash being thrown around!

Top Photo Credit: John E. Sokolowski/USA TODAY Sports