A Look Back at the Most Impactful NBA 2020 Trades and Their Legacy

2025-11-17 11:00

I still remember the chaos of that 2020 NBA trade deadline like it was yesterday. The air in the league offices felt electric, with phones buzzing nonstop and reporters scrambling for scoops. Looking back now, I can't help but think about that Filipino saying that kept popping into my head during those wild days: "Sumabay na rin ako kung saan ako dinala ng sistema" – I just went with where the system took me. That's exactly what happened across the NBA landscape that year, as franchises and players alike rode the unpredictable currents of what would become some of the most transformative trades in recent memory.

The James Harden blockbuster to Brooklyn stands out as the defining move of that period, a seismic shift that reshaped the Eastern Conference for years to come. I'll admit, when I first heard the Rockets were seriously considering moving their franchise cornerstone, I was skeptical. Harden had just averaged 34.3 points per game the previous season – astronomical numbers that made him virtually untouchable in my eyes. But the system had other plans. The Nets sent out a staggering package: four first-round picks, four pick swaps, plus Caris LeVert and Jarrett Allen heading to Indiana and Cleveland respectively in the three-team deal. What fascinated me most wasn't just the sheer volume of assets changing hands, but how this trade created ripple effects throughout the entire league. Brooklyn instantly became the team to beat in the East, while Cleveland unexpectedly found their defensive anchor in Allen. Sometimes you have to marvel at how these moves work out – teams just go with where the system takes them, and the results can be astonishing.

Meanwhile, out West, the Clippers were making their own calculated gamble on Paul George. To get PG-13, they shipped Shai Gilgeous-Alexander, Danilo Gallinari, and five first-round picks to Oklahoma City. At the time, I thought the Clippers overpaid dramatically, and frankly, I still believe they did. But here's where that "going with the system" mentality really applies – the Thunder's rebuild accelerated lightyears ahead of schedule because they recognized where the currents were flowing. They accumulated draft capital like nobody's business, while the Clippers bet their immediate future on creating a Los Angeles superteam. Both approaches made sense in their own contexts, though I've always leaned toward valuing sustained team-building over splashy superstar acquisitions. The Thunder's patience has already started paying dividends with Chet Holmgren and Jalen Williams developing into cornerstones, while the Clippers' championship window with that core has officially closed without a single Finals appearance to show for it.

The Jrue Holiday trade often gets overshadowed by the bigger names, but in my professional opinion, this was the most intelligently executed move of that trade period. Milwaukee sent Eric Bledsoe, George Hill, three first-round picks, and two pick swaps to New Orleans for Holiday. What made this trade special wasn't just the player Milwaukee acquired, but the perfect fit he represented. Holiday provided the two-way stability that Giannis Antetokounmpo desperately needed alongside him, and the proof came just months later when they hoisted the Larry O'Brien trophy. The Bucks identified exactly what their system required and went after it with precision, while the Pelicans secured valuable future assets that eventually helped them build around Zion Williamson. This is the kind of trade that exemplifies smart team-building – both franchises understood their positions in the ecosystem and made moves accordingly.

Reflecting on these deals four years later, the legacy is clearer than ever. The Harden trade created a superstar carousel that's still spinning today, with players increasingly dictating their destinations. The PG-13 deal demonstrated both the risks of going all-in and the rewards of strategic patience. And the Holiday transaction reminded us that sometimes the best moves aren't the flashiest ones, but the ones that complete a team's identity. The NBA's ecosystem operates like a complex river system – teams and players must navigate currents they can't always control, making decisions with imperfect information. That 2020 trade period taught me to appreciate the artistry in front office decision-making, where sometimes the smartest move is indeed to just go with where the system takes you, while other times it requires fighting against the current to carve your own path. The teams that understood this balance – knowing when to ride the wave and when to paddle against it – are the ones that ultimately positioned themselves for sustained success in the years that followed.

football game