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How the summer of 2019 shaped this year’s playoffs

A quiet move four years ago put the league in a stranglehold.

Miami Heat v Philadelphia 76ers Photo by Rich Schultz/Getty Images

Do you remember free agency in July 2019? Kawhi Leonard had just pulled the Toronto Raptors to their lone Title by defeating an injury depleted Golden State Warriors team in six games. I thought the most interesting part of the series was that the best player from each team were very likely moving to other franchises as free agents in the summer – regardless of the outcome of the NBA Finals. Nobody knew where exactly Durant or Leonard would go, but any team with even a tiny chance of getting either player would move heaven and earth to make it happen. The opportunity to have one of the top 5 players in the world on your team doesn’t happen every day, and whoever signed either would presumably be replacing the Raptors or Warriors in the NBA Finals for the foreseeable future.

While taking the Raptors to The Finals John Wick style, Kawhi dispatched the team of another important free agent to be: Jimmy Butler and the Philadelphia 76ers. It took the full seven games, and four bounces around the rim on his three pointer from the corner as time expired to reach the Eastern Finals. There they faced the Milwaukee Bucks, who had previously finished off the Boston Celtics and Kyrie Irving, yet another free agent to be. Meanwhile, Kevin Durant’s Warriors had beaten the James Harden – Chris Paul Houston Rockets, and then swept the Portland Trail Blazers.

(I’ll pause here while you watch the last two minutes of Game 5, which, despite Paul George’s comments post-game, may have influenced his willingness to answer his phone in the early days of July. Also, my favorite part of the video you just watched is CJ turning to wave goodbye and the look of glee on his face as he realizes what’s happening.)

Watching the 2023 First Round has me thinking a lot about those four John Wick bounces Kawhi got, and the influence they continue to have on the NBA.

Durant chose Brooklyn and Kyrie Irving as his new running mate. Leonard chose the Clippers, but only if they were able to trade for Paul George, which they were more than happy to do. Shai Gilgeous-Alexander, Danilo Gallinari, plus 5 draft picks, only one of which is protected, plus two more pick swaps for PG and the reigning NBA Finals MVP. In the moment, the Clippers appeared to have won the summer. With a single move, they attempted to shed their entire Clippers history, and move forward with a team as competitive, if not outright better than, their neighbors across the hall, Anthony Davis and LeBron James. Meanwhile, a multitude of decisions made in Philadelphia led to Jimmy Butler being signed and traded to the Miami Heat.

Two other teams were needed to make the money work. The Portland Trail Blazers —fresh off being swept in the Conference Finals— took Hassan Whiteside’s contract in exchange for Meyers Leonard, and sent Moe Harkless to the Clippers. Miami sent Josh Richardson to Philadelphia and a pick that would later be used in the George trade to Los Angeles. When the move was completed, Philadelphia felt confident moving forward with Richardson and Simmons as their guard pairing, Los Angeles had gotten another asset to use in acquiring George, the Blazers had seemingly added the big man who could prevent them from being swept next time they faced Golden State in the playoffs, and Miami had their first star since the Spurs beat LeBron James so bad he decided to take his ball and go home.

This is the point where I learned to think about basketball on a different level. As a Portland fan, I must admit I drank a bit of the Kool Aid, and was excited for Hassan Whiteside to join my favorite team. After watching him play for exactly one week, I began to wonder why Neil Olshey had helped facilitate a trade in which they did not send away or receive the best player involved. A few months later, everyone would start to wonder why Philadelphia had chosen Simmons over Butler.

Philadelphia’s decision has two main components: on court production, and off court dynamics. Simmons had been the primary ball handler during the regular season, but come playoff time, Brett Brown moved Butler on ball, and designated Simmons secondary ball handler. From a front office perspective, if you want to see Simmons’ full potential as a ball handler, the money that would be spent on Butler’s duplicative skill set could theoretically be used to fill other holes in the roster. Remember this is when Simmons’ value was nearly at its peak (He hadn’t yet avoided a wide-open, point-blank layup against Atlanta) and deciding to keep Simmons over Butler long term was a defensible choice. In fact, many smart basketball people were thoroughly excited to see Richardson in Philly, and thought he would be a great addition to the Embiid-Simmons pairing. Off-court dynamics might have played a larger role in both Butler and Philadelphia’s decision.

Butler arrived in Philly partially because of the timing of an ESPN interview the previous summer. According to Butler, the interview was planned for weeks, and he’d already been in discussions with management in Minnesota about a trade. The interview took place after a practice where, again, according to Butler, an unnamed member of management demanded he practice with the starters, despite the team being close to finalizing a deal to trade him. This led to Butler scrimmaging with the backups, and trash talking everyone in sight, including management and ownership, who were in the gym. Butler had spent enough time with Towns and Wiggins to know that “This ain’t it” as he told JJ Redick in December of 2018. (Which makes me wonder if Butler spent enough time with Simmons in just one season to know, way back in July of 2019, what we all know now.) Regardless, Butler landing in Miami did not have near the perceived impact of Durant and Irving to Brooklyn, or Leonard and George to the Clippers. It didn’t even have a negative impact on public opinion of Philadelphia’s decision-making until Simmons’ on court production became a problem.

Let’s look at some stats since those contracts were signed, focusing on Leonard, Simmons, Durant, Irving and Butler. During his Clippers tenure, Leonard has averaged 25 points, 4.5 assists, and almost 7 rebounds per game with an effective FG% of 55 in 33 minutes per game. In his first season, they took the Denver Nuggets to 7 games in the second round. The next year, they made the Conference Finals and faced the Phoenix Suns, but Leonard didn’t play due to injury. Last year Kawhi did not play a game.

Durant missed his entire first season with the Nets, recovering from the achilles injury he suffered in the Finals. He then played 35 and 55 games, before submitting and rescinding a trade request at the start of this season. He played 39 games for the Nets this year before being traded to Phoenix. In Brooklyn Durant averaged 29 points, 6 assists and 7 rebounds with an eFG% of 59 in 35 minutes per game. Irving played 20, 54 and then 29 games for the Nets in his first three seasons. His tenure there was defined by off-court issues, which led the team to acquiesce his trade request after 40 games of this season. Including 13 playoff games, he totaled 101 games across 4 seasons in Brooklyn.

Simmons meanwhile, could not successfully assume the role of lead ball handler on a contending team, and was sent to the Nets after essentially refusing to play for Philly. I think he got injured again after Durant and Irving were traded, but honestly, it’s currently unclear if he’s even interested in playing professional basketball anymore. His appearances this year were disheartened efforts at best. Durant played 7 more playoff games than Irving, but only 120 in total for the Nets. Leonard has 187 games played since arriving in LA, including 26 in the playoffs. Butler has played at least 52 games each of the last 4 years. During his Miami tenure, he’s averaging 21.5 points, 6 assists and 6 rebounds on 51% effective FG in 33 minutes per game. He led the Heat to the Finals against the Lakers in the bubble season. With 46 playoff games through Monday, Butler has played a grand total of 277 games in a Miami uniform. He’s played 20 more playoff games than Leonard, 26 more than Durant, and 33 more than Irving. Simmons played 12 playoff games with Philly in 20-21, which ultimately led to the franchises decision to move on. Butler is the only of the four free agents to make The Finals since 2019. The day after the contracts were signed, if I’d told you how lopsided these numbers would be, who’d have believed me?

On Tuesday, the 8 seeded Wolves, now sans Wiggins, ended their season with a loss to the top-seeded Nuggets. Philadelphia, now without Simmons, await the Celtics. The Clippers season ended at the hands of Durant and the Phoenix Suns, Leonard only played 2 of the 5 games, and waited until the series ended to inform the public that his meniscus is torn and he wouldn’t have played any more this season even if the Clippers had found a way to beat Phoenix. Irving’s Dallas Mavericks failed to make the playoffs and only managed to win 9 of 25 games with him. Nobody knows when, where or if Simmons will play basketball next, with his last game for the Nets being a 2 point outing over two months ago against Butler and the Heat.

And Butler? He’s singlehandedly led the Miami Heat to a 5 game upset of the top seeded Bucks, becoming just the 6th eight seed to win a first round playoff series in NBA history.

Sure Giannis basically played two games of the five. But the Bucks have Jrue Holiday, Kris Middleton, Brook Lopez, Bobby Portis, and a host of wings who should be able to beat a Heat team that lost their first play-in game to the Atlanta Hawks, and barely beat the Chicago Bulls for the right to be the eight seed. The Heat start Max Strus, Gabe Vincent and washed Kevin Love for crying out loud! Duncan Robinson played 30 minutes in game 4 after being glued to the bench all season. Someone named Haywood Highsmith played 14 minutes of their most important game of the season! Caleb Martin is potentially their best wing defender aside from Butler. The Bucks should have absolutely annihilated this Heat team. Yet, a squad of rangy, athletic wings around 3 of the best defenders in the game can’t contain Jimmy freaking Butler. He followed his 56 point, 9 rebound outburst on Monday (where he dominated every phase of the game) with 42-8-4 in an OT road win — a game in which the Heat trailed by 16 to begin fourth. His precision, determination, and will to win make him look like an assassin on the court.

Hypotheticals can be silly, but hear me out. Does Philly let Butler walk if Leonard misses that shot from the corner, and the 6ers move on to the Conference Finals? Regardless of the outcome of that series, where could Philly be if they kept Butler instead of adding Al Horford? What if Philly ignored the off-court noise, paid attention to the on court product, and build around their playoff lead ball handler? Where would the Clippers be if they signed Butler and traded for George? What if Lillard misses that shot you’re still thinking about, the Thunder capitalize on their momentum, and make a Conference Finals run? Does Sam Presti refuse to engage the Clippers when they call about George? What if Portland paid attention to their on court needs and attempted to pair Butler with Lillard instead of taking Whiteside’s contract? What would Toronto have done the next season if they replaced Leonard with Butler? What would the Nets look like if they’d paired Durant and Butler? These are all ridiculous, unanswerable questions, but maybe there’s one definitive answer: Leonard won that ring in Toronto, but John Wick moved to Miami the following summer.