Top NBA Free Agents in 2019 and 2020: Where Are They Now and How They Impacted the League

I still remember watching Alex Eala step onto Centre Court for her Wimbledon debut, thinking how one moment can define a career trajectory. That same principle applies to NBA free agency, where a single decision can reshape franchises and alter legacies. Looking back at the 2019 and 2020 free agency classes feels like examining a time capsule of what-could-have-been and what-actually-transpired. These players weren't just chasing contracts—they were chasing history, much like Eala chasing her Wimbledon dream, though in their case it was about championships, legacy, and their place in basketball lore.

The 2019 class was particularly fascinating because it came during a transitional period for the league. Kawhi Leonard's decision to join the Clippers created this seismic shift that we're still feeling today. I've always believed that move single-handedly changed how teams approach star acquisitions. He wasn't just signing with a team—he was essentially creating a new contender overnight by bringing Paul George with him. The Clippers gave up what, five first-round picks and two pick swaps? That's the kind of gamble that either makes you look like a genius or gets you fired. Four years later, I'd say they're somewhere in between—they've had moments of brilliance but haven't broken through to that championship level, partly due to injuries that have plagued both stars.

Then there was Kevin Durant choosing Brooklyn, which at the time felt like the beginning of a new dynasty. I remember thinking the Nets were positioned to dominate the East for years. Instead, what we got was three and a half seasons of drama, underachievement, and ultimately a messy divorce. Durant's impact goes beyond just his incredible scoring—his move to Phoenix has reshaped the Western Conference landscape entirely. The Suns gave up Mikal Bridges, Cam Johnson, and four unprotected first-round picks for him, which tells you how highly teams still value elite talent even when they're deeper into their careers.

What's interesting to me is how differently the 2020 class has aged. While 2019 was about established superstars changing addresses, 2020 felt more like teams making calculated bets on potential. Gordon Hayward to Charlotte never quite worked out the way either side hoped—he played about 45% of possible games during his tenure there. Meanwhile, Fred VanVleet's rise from undrafted to max contract with Toronto represents one of the better development stories in recent memory. His subsequent move to Houston this past offseason shows how the market continues to value two-way guards who can lead an offense.

The financial landscape has shifted dramatically since these signings. In 2019, the average starter-level player was commanding around $18-22 million annually, whereas today that number has jumped to roughly $25-30 million. This inflation affects how we judge these contracts in hindsight—what seemed like an overpay then might look reasonable now, and vice versa. For instance, Tobias Harris's five-year, $180 million deal with Philadelphia was heavily criticized, but he's been remarkably consistent even if not quite living up to that massive number.

What often gets lost in these discussions is how these signings impact team construction beyond just the court. When a team signs a major free agent, it affects their flexibility, their ability to retain role players, and their draft strategy. The Celtics losing Gordon Hayward in 2020 actually created the trade exception that eventually helped them acquire Evan Fournier, who then became part of the package for Derrick White. It's this domino effect that makes free agency so compelling to analyze years later.

From my perspective, the most successful signings have been the second-tier players who provided stability rather than superstars chasing rings. Jae Crowder's move to Phoenix in 2020 gave them the defensive versatility they needed to reach the Finals. Joe Harris staying in Brooklyn gave them years of elite shooting before injuries derailed his effectiveness. These are the moves that often fly under the radar but genuinely shape team identities.

The international influence can't be ignored either. While Alex Eala represents the global growth of tennis, NBA free agency has become increasingly international. The Raptors building around Pascal Siakam and OG Anunoby after Kawhi's departure shows how teams are valuing global talent development. In fact, about 25% of rotation players in the NBA now were born outside the US, which absolutely affects free agency strategy and valuation.

Reflecting on these classes, I'm struck by how unpredictable player development remains. Who would have predicted Jordan Poole becoming a champion and max player after being drafted late in the first round? Or that Christian Wood would bounce around multiple teams despite putting up impressive numbers? The variance in outcomes reminds me that for all our analytics and projections, basketball remains human—affected by chemistry, health, and plain old luck.

As we move further from these signing periods, their true impact becomes clearer. The 2019 class reshaped the league's power structure more dramatically, while 2020 reinforced the importance of role players and financial flexibility. Both classes taught us that the biggest names don't always provide the best value, and that sometimes the most impactful moves are the ones that don't make headlines but steadily contribute to winning cultures. Just as Alex Eala's Wimbledon journey represents the beginning of a career arc, these free agency decisions represent pivotal moments that continue to influence the NBA landscape years later, proving that in basketball as in tennis, today's moves create tomorrow's legacy.