One of the more underrated storylines of the 2019-20 NBA season was the San Antonio Spurs‘ failure to reach the playoffs.

The Spurs have been a franchise steeped in tradition and excellence for the better part of two-plus decades, with the tradition simply being winning.

San Antonio made the playoffs in each year between 1998 and 2019, with head coach Gregg Popovich presiding over one of the most incredible runs in league history.

Even as the playoff streak came to an end, the Spurs still made a late charge in Orlando. San Antonio started the NBA restart at 2-2, but reeled off three consecutive wins before falling to the Utah Jazz in the final seeding game.

It truly marked the end of an era. More importantly, it signaled the uncertainty that would follow San Antonio in the coming months.

The Spurs no longer have franchise stalwarts like Tim Duncan, Manu Ginobili, or Tony Parker. They lack budding talents such as Kawhi Leonard, whose ascension to the top of the NBA began in San Antonio.

Needless to say, the Spurs faced a number of challenges entering the offseason. Some of those questions remain unanswered.

Here is a closer look at San Antonio's offseason.

The Draft

One of the greatest strengths of the Spurs organization is its strong drafting record and history of player development.

Keldon Johnson hardly played during the regular season. But he was one of the stories of the NBA bubble, even scoring 24 points in each of the team's last two games. Even Luka Samanic showed glimpses in the final seeding game despite making just three appearances. The 2019 group would be considered an underwhelming class, yet they still have upside.

In any case, San Antonio has made its draft picks count, hence the sustained success.

The Spurs had another opportunity to find a pair of strong players last month, and they might have struck gold.

Devin Vassell fell to San Antonio with the No. 11 pick, and Spurs fans should be extremely excited about the former Florida State product. Vassell is exactly the kind of defensive wing who typically thrives in Popovich's system, and he could have gone in the top-5 considering teams like the Golden State Warriors expressed interest.

Vassell can shoot it from deep and has explosive athleticism. If he hones his shot-creation and becomes a more aggressive offensive threat, his ceiling will only continue to grow.

The Spurs drafted Tre Jones in the second round, which was another sound move. Jones fits in San Antonio with his ruthless on-ball defense and tremendous instincts. The former Duke star also showed dramatic improvement shooting the ball from the perimeter while also being capable of getting into the lane and making plays around the rim.

San Antonio has a number of backcourt players on the roster, but Jones can defend, distribute and rebound from the point guard spot. He should get his minutes.

Nothing about San Antonio's draft process was very flashy, nor were the picks. These are the Spurs, after all.

Still, the team seemingly picked up a pair of winning players who defend and compete at a high level.

Grade: A-

Free Agency

The Spurs had a quiet free agency mostly focused on maintenance.

San Antonio re-signed Drew Eubanks and Jakob Poeltl for frontcourt depth. The Poeltl contract was essentially a no-brainer given his efficiency and shot-blocking ability. He should continue to see more and more playing time in the next few years.

The Spurs also re-upped with Quinndary Weatherspoon, the team's second-round pick from last season, and signed Keita Bates-Diop to a two-way contract.

But the most impactful signing is a loss. Bryn Forbes inked a two-year deal with the Milwaukee Bucks, depriving the Spurs of one of their best perimeter shooters. Marco Belinelli also signed a deal to return to his native Italy, robbing San Antonio of more shooting off the bench.

There was not a whole lot the Spurs could do in free agency due to financial inflexibility. Retaining Poeltl was prudent, but losing Forbes still hurts, even if San Antonio hopes Vassell can add shooting.

In the grand scheme of things, however, free agency was mostly a wash.

Grade: C

The DeMar DeRozan conundrum

We cannot talk about San Antonio's offseason without going into detail on DeRozan. He is the reason they lack financial flexibility, after all.

There were plenty of rumors surrounding the four-time All-Star. Initially, it appeared a certainty DeRozan would exercise his $27.7 million player option for this season. But then reports surfaced the former USC product was unhappy in San Antonio, rending his future somewhat uncertain.

Kevin O'Connor of The Ringer reported the Los Angeles Lakers had interest in trading for DeRozan by offering a package including Kyle Kuzma. But general manager Rob Pelinka has seemed to offer his support in making Kuzma part of the team's future, and the Lakers addressed the roster in other ways.

The Spurs had hopes in packaging DeRozan in an effort to move up in the draft. But those efforts also proved fruitless.

Ultimately, DeRozan was resigned to exercising the option.

The 31-year-old is still a tremendous offensive playmaker. DeRozan averaged 22.1 points, 5.6 assists and 5.5 rebounds this past season while shooting over 53 percent from the field. But he is also a midrange scorer who does not fit the Spurs' system and has obviously expressed some discontent with his situation.

It is possible–likely even–the Spurs deal DeRozan at the deadline. But for now, he is stuck playing out the final year of his deal on a team in transition.

Grade: C-

Overview

San Antonio is still sort of between a rock and a hard place.

The Spurs' two “stars” (DeRozan and LaMarcus Aldridge) are aging vets on big deals. The young guys have all flashed potential at one point or another, but none have been able to get higher usage in part because DeRozan and Aldridge are still on the roster.

As such, the Spurs had no other choice but to essentially sit this offseason out, especially since it seems DeRozan had little trade value.

This offseason could look a whole lot better if Vassell quickly develops into a future franchise player. But the lack of offseason activity outside the draft probably means the Spurs are no better than a fringe playoff team–if that–in a reloaded Western Conference.

The 2020-21 season could be the equivalent of a punt in preparation for next summer when both DeRozan and Aldridge are off the books.