Are Spurs about to make mistake with Kawhi Leonard?

As NBA analysis goes, there's one tenet that has held true for, oh, nearly two decades now: Don't question the San Antonio Spurs.

If any organization in all of professional sports knows what it's doing, it's the Gregg-Popovich/RC Buford-led bunch that has won five titles since 1999 despite fighting all the uphill battles that come with being a small market team in the NBA. Yet as the defending champions start this season that might very well be the last of the Tim Duncan era, it's worth wondering if they're about to make a rare mistake that might eventually complicate this inevitable transition into a new time: the decision not to give Kawhi Leonard the five-year, $90 million maximum-salary contract extension he so desires.

While the fourth-year player and the Spurs still have until Friday to get a deal done, all indications point to the Spurs not giving Leonard the deal he wants. Never mind that Popovich offered Leonard the highest of praise two years ago when he said "he'll be the face of the Spurs," or that Leonard went into the summer with all the momentum of being named the Finals MVP.

One can even try and forget that Leonard is clearly the only Spurs player not in his 30s who appears capable of leading them as a centerpiece player in the post-Duncan/Ginobili era. All that aside, there's this bottom line on the business front: waiting for resolution via restricted free agency next summer comes with the kind of risk that even the Spurs may ultimately regret.

As we learned in the Chandler Parsons saga between the Houston Rockets and Dallas Mavericks during the summer, when the Mavericks structured a three-year, $46 million offer that included a player opt-out after two seasons and a pricey trade kicker (15%) that prompted the Rockets to let him walk, it's not always as simple as the incumbent team matching the best offer that come their player's way.

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The structure and length of the contract are key components, especially in an environment like that of the Spurs' where they place such a premium on stability as they forge closer to this unknown future. And while the Spurs have done such masterful work over these last few decades convincing players to sacrifice on the financial front for the greater good, the harsh reality is that they simply can't assume that trend is going to continue.

Especially considering the context that surrounds Leonard and his ongoing negotiations.

Parsons' situation remains the most applicable. Then comes Gordon Hayward, a 24-year-old who has put up good numbers (12.4 points, 3.4 rebounds, 3.1 assists per game) on Utah Jazz teams that have been subpar for his four seasons (143-169 regular season record combined). He was given a four-year, $63 million deal max offer by the Charlotte Hornets last summer that the Jazz matched.

The Golden State Warriors' Klay Thompson finds himself in a similar situation to Leonard, that of a talented two-way, perimeter player whose team is hoping to land him for less than the max extension he believes he deserves. Former Indiana Pacers guard Lance Stephenson hit the free agent market as a dynamic two-way talent as well, but the baggage that came with all his well-chronicled antics surely played a part in the Hornets' ability to get a relative bargain (three years, $27 million).

The moral of most of their stories, of course, is that young players with good reputations, dynamic talent and an upward arc to their career don't come cheap.

Leonard's production, some will surely argue, does not reflect that of a max player. The fourth-year player averaged 12.8 points, 6.2 rebounds, two assists and 1.7 steals per game last season. But as anyone who has seen his evolution over these past few years is well, the numbers don't come close to quantifying his impact.

Beyond being an elite defender – the kind that is so vital with the likes of LeBron James, Kevin Durant, Carmelo Anthony and (when healthy) Paul George at his position – separates him from most of the league's small forward field. What's more, there are plenty of signs that Leonard is capable of blossoming into an All-Star level scorer. Infamously-quiet though Leonard may be, the San Diego State product has never been shy about sharing the fact that he has big dreams in this league.

Last November, after the Spurs routed the New York Knicks in the seventh game of the season, Leonard – who hit seven of 10 shots in that game for 18 points – was asked by a reporter on hand whether he thought he could ever be on Anthony's level offensively.

"Oh yeah," he replied with the kind of confidence that he always seems to carry.

Being the new kid on the block has a way of lessening a young player's impact, of course, and so it was that Leonard finished the season third on the Spurs in field-goal attempts (9.8) with Ginobili (9.2), Marco Bellinelli (8.7), Patty Mills (8.2), Danny Green (7.4), and Boris Diaw (7.3) not far behind. But those days are clearly nearing an end, and the fact that Leonard's efficiency only improved with his increased workload last season is the kind of trend that's worth investing in. After entering the league with questions about his shooting range and working to hard with Spurs shooting guru Chip Engelland to remedy that situation, he posted career highs in field-goal percentage (52.2) and three-point accuracy (37.9%).

But how long is Leonard willing to play fourth fiddle in this franchise, and what happens if this deal doesn't get done and he spends the season wondering how he'd look in a different uniform? It wouldn't be the first time resentment was born out of these sorts of situations, and rest assured that the relationship – on both sides of this equation – must remain rock-solid if this is going to work for the long haul.

The puzzling part is that the Spurs spent the summer checking every vital box they had other than Leonard. Popovich and Parker received extensions, and super subs Diaw and Mills got new contracts too. The Spurs, who have approximately $33 million in payroll for next season committed with the salary cap projected to be $66.5 million, are surely hoping to hold on to their financial flexibility for next summer and perhaps to replace Duncan with a free agent big man of their dreams (Marc Gasol, anyone?) should The Big Fundamental finally retire.

But why not let Leonard know that he's the one to lead them into the post-Duncan days, especially when his incentive for cutting a short-term deal is so evident? If Leonard were to sign a two-year contract and become a free agent in the summer of 2017, the league would be entering the second season of its nine-year, $24 billion television rights contract with ESPN and Turner right about the time the salary cap was soaring like never before. Leonard, meanwhile, would be 26 years old and in prime position to get a max deal of a far-pricier kind.

The Spurs being the Spurs, they'll likely figure this out like they do everything else. But locking up Leonard, make no mistake, is the way to go.