Both Kawhi Leonard trades will always be remembered (Photos via Twitter)

As the 2010s come to a close, the San Antonio Spurs have enjoyed a remarkable amount of success this decade. However, with the start of the next decade looming, they will be hard pressed to replicate it.

The front office — consisting of RC Buford, Gregg Popovich and new GM Brian Wright — deserves a lot of credit for the past success. That said, they can’t escape the blame for the bad moves.

The past few years haven’t been as well managed as the first several seasons of the decade. The team has suffered as a result. Several decisions have led to varying levels of failure — and a future than is uncertain.

5. The Nikola Milutinov Situation

While the Spurs 2015 offseason was highly successful, there was a misstep that occurred before free agency even began. The Spurs drafted Nikola Milutinov with the 26th pick in the draft. Five seasons later, he has yet to play a game for the Spurs.

It’s clear that Milutinov was partly selected because he was willing to stay overseas for at least a season, as the goal for that offseason was to preserve cap space in order to sign LaMarcus Aldridge to a max contract.

The salary cap rose several million more than the initial projections, however. It was indeed possible that both Aldridge, Kawhi Leonard and the salary of the 26th pick would’ve fit under the salary cap. Players such as Larry Nance Jr, Kevon Looney, Montrezl Harrell and Josh Richardson were available had the front office decided against the draft-and-stash route.

Milutinov is nearly 25 and in the final season of his contract with Olympiacos. He’s turned into a solid center, averaging 11.1 points and 9.3 rebounds in 26.3 minutes per game in EuroLeague.

Should he finally join the Spurs next season, he will no longer bound to the rookie scale salary structure. That means that Milutinov could ask for significantly more than what most centers are worth in the NBA. As he’s become a top player in Europe, there’s little incentive for him to come over if the Spurs don’t offer a competitive salary.

There are also overlap concerns with Jakob Poeltl, who is both younger and a proven NBA center. Milutinov is an excellent finisher and a strong rebounder but he’s not as mobile as Poeltl, so he may struggle to defend out on the perimeter.

San Antonio may be better off re-signing Poeltl, signing a center in free agency or seeing if Chimezie Metu can develop further. It’s looking increasingly likely that the Spurs wasted a first round pick.

4. The 2017 Offseason

Following consecutive 60-win seasons and a Western Conference Finals run, the Spurs had a chance to build upon their success. San Antonio did the opposite, however, with a series of poor moves in the summer of 2017.

The Spurs replaced the successful pairing of David Lee and Dewayne Dedmon by re-signing Pau Gasol and signing Joffrey Lauvergne. Gasol’s three-year, $48 million deal, with $39 million guaranteed, marked a drastic overpay for a 37-year-old center.

It’s possible that the contract was a result of the Spurs returning the favor for Gasol opting out of his $16 million player option. The goal was to pursue other free agents — but the Spurs struck out. In any case, what resulted was a wildly overpriced contract for Gasol. The deal was made worse when considering he wasn’t significantly better than Lee or Dedmon.

Buford stated that “we never envisioned that he (Lauvergne) would become available.” It quickly became apparent why he was available. Lauvergne struggled early, on both ends, and was out of the rotation by January. Even with only two other big men on the roster, Lauvergne remained in the dog house. After the season, he (luckily) declined his player-option and signed with a team in EuroLeague.

Also at the start of the 2017 offseason, Patty Mills signed with a four-year, $50 million deal. The contract has become polarizing, with some viewing it as an overpay and others viewing it as a worthwhile investment for a top-flight bench player and a team leader. With Mills’ solid play, and yearly raises to the salary cap, the deal may fall somewhere in the middle now. Still, re-signing Mills felt more like a fallback option than the main goal. There were rumors of Chris Paul or even Mike Conley being linked to the Spurs.

Brandon Paul was signed as a potential 3-and-D wing. Paul essentially replaced Jonathan Simmons, who the Spurs let walk after a solid postseason performance. While letting Simmons sign elsewhere worked out, Paul didn’t. He never shot the ball well enough to fill a role on a team that desperately needed shooting.

The Spurs did draft Derrick White and signed Rudy Gay in the same offseason, preventing it from being a complete disaster. However, with Kevin Durant joining Golden State and Chris Paul joining up with James Harden, the lackluster offseason likely didn’t sit well with Kawhi Leonard.

3. The Davis Bertans Trade

San Antonio traded Davis Bertans to the Washington Wizards as part of a three-team deal that also included the Brooklyn Nets trading DeMarre Carroll to the Spurs. The trade allowed for the Spurs to preserve their mid-level exception and sign Marcus Morris. That, of course, never happened and what resulted was a mess. Bertans is currently having a career-year with the Wizards while Carroll is chained to the bench with the Spurs.

Morris deserves plenty of blame for going back on his word, as well as the pettiness of the New York Knicks for pursuing him. Unfortunately for the Spurs, Morris is having a career year for the Knicks, averaging 18.7 points, while shooting 47.2% on 5.9 three-pointers per game.

In hindsight, it’s also fair to blame San Antonio for not fully utilizing Bertans. He’s been fully unleashed in Washington — taking more three-pointers per game than in each of the last two seasons combined. At 44.7%, Bertans is shooting a career-high on threes, along with a scoring average of 15.6 points per game. Bertans never had that freedom in San Antonio, despite his clear positive impact on the Spurs offense.

Getting both Morris and Carroll was meant to bolster the Spurs defense, after finishing 20th last season, as well as add two high volume three-point shooters. Instead, San Antonio got only Carroll, who has barely played thus far.

Trey Lyles was signed to try and fill the void left by the Bertans trade and Morris not signing — but the results have been mixed. Lyles has flashed some utility but is currently shooting below league average from three-point range.

2. The Richard Jefferson Contract

Richard Jefferson — then an athletic, high-scoring wing — was traded to the Spurs for the expiring deals of Bruce Bowen, Fabricio Oberto and Kurt Thomas. There were high expectations for the 29-year-old Jefferson, who was supposed to help San Antonio extend their title window. It didn’t exactly work out that way.

He struggled to fit in playing alongside Tim Duncan, Manu Ginobili and Tony Parker — and was essentially a fourth option. Playing without the ball in his hands, Jefferson was relegated to spotting up. Add in inconsistent defense and an underwhelming playoff performance, and Jefferson’s first season with the Spurs went about as poorly as could’ve been expected.

Despite that, Jefferson and the Spurs came to an agreement on a new four-year, $39 million deal. While Jefferson worked hard to improve his three-point shot, shooting over 40% in the final season and a half of his Spurs career, he never fit in and was ultimately sent packing.

With the emergence of Kawhi Leonard, Richard Jefferson became expendable and was traded along with a first-round pick to Golden State for Stephen Jackson. The move allowed for Leonard to become a full-time starter, however the move cost the team a first rounder.

The pick ultimately ended up being the 30th pick. Then again, San Antonio lost out on several potential players as a result of re-signing an ill-fitting player. Players drafted in the second round that year include Draymond Green, Khris Middleton, Jae Crowder and Will Barton.

1. The Kawhi Leonard Trade

The Spurs-Raptors trade is, far and away, the worst front office decision of the decade for the Spurs. Leonard demanded a trade in the summer of 2018, forcing San Antonio’s hand and limiting their options. It was clear that Leonard wanted to play in L.A. and even clearer that the Spurs didn’t want to send him there. That decision appears to have hurt the Spurs in the long run.

According to reports, the Clippers were willing to move Tobias Harris as well the 14th and/or 15th pick in a package for Leonard. Boston reportedly offered as many as three first rounders, while the Lakers reportedly offered Kyle Kuzma, Brandon Ingram and picks.

Ultimately, the Spurs settled on Toronto’s package of DeMar DeRozan, a first round pick and Jakob Poeltl. Initially, it was rumored that Gasol would be in the deal. Had that been the case then it would’ve been a significantly better deal for the Spurs. In in the end, the Spurs traded Danny Green instead of Gasol.

DeRozan’s fit with the Spurs would’ve been far better playing alongside Derrick White and Danny Green in the starting lineup. Having two above average defenders on the perimeter would’ve allowed for DeRozan to hide more easily on defense.

Had that been the case, DeRozan’s biggest weakness would’ve been minimized. Instead, Green had an excellent season in Toronto, playing outstanding defense while shooting a career-high 45.5% on three-pointers.

Poeltl became a solid rotation player (and a possible future starter) while Keldon Johnson, the player selected with the Raptors’ pick, shows promise. DeRozan has lived up to his reputation as a very talented but deeply flawed player. Averaging 21.1 points, 5.8 rebounds and 5.8 assists, DeRozan has struggled to shoot threes and struggled to play winning basketball in his 105 games in San Antonio.

Making the Raptors deal has led directly to the mediocrity that the Spurs find themselves in. Pairing Aldridge and DeRozan together was a poor decision, guaranteeing the Spurs would have spacing issues and thus limiting the types of players that can play alongside them.

San Antonio ranks 15th in offense, 22nd in defense and dead last in three-pointers attempted en route to a 12-17 record. DeRozan shares blame for all three categories. The front office will have their work cut out for them trying to right the ship heading into the 2020s.

In the end, the decade’s best trade and worst trade both involved Kawhi Leonard. The trade to acquire Leonard propelled the Spurs back into into title contention. Unfortunately, the trade that sent Leonard away ensured that San Antonio wouldn’t compete for a championship in the near future.