NBA 2020 Trades: Which Teams Won the Biggest Deals and Lost the Most?

Looking back at the whirlwind of trades during the 2020 NBA season, I can’t help but reflect on how certain teams truly rode the wave—almost like that saying, "Sumabay na rin ako kung saan ako dinala ng sistema." You just go with the flow, adapt, and sometimes you strike gold. As someone who’s followed the league for over a decade, I’ve seen blockbuster deals that reshaped franchises overnight, and 2020 was no exception. In this piece, I’ll break down which teams came out on top and which ones stumbled, blending data, insider observations, and a bit of my own bias—because let’s be honest, neutrality is overrated in sports analysis.

Starting with the clear winners, the Milwaukee Bucks’ acquisition of Jrue Holiday stands out as a masterstroke. They sent Eric Bledsoe, George Hill, and three first-round picks to the Pelicans, a hefty price that raised eyebrows initially. But Holiday’s impact was immediate: he averaged 17.7 points and 6.1 assists per game in the 2020-21 season, and his defensive prowess was a game-changer. I remember watching him lock down opposing guards; it felt like the Bucks finally had that missing piece to complement Giannis Antetokounmpo. They went on to win the 2021 NBA Championship, and in my view, that trade was the catalyst. Sure, they gave up a lot, but championships aren’t won by playing it safe. On the flip side, the New Orleans Pelicans might have gotten a haul, but they’re still figuring things out—sometimes, accumulating assets doesn’t translate to wins if the system isn’t right.

Then there’s the Los Angeles Clippers, who landed Luke Kennard in a sign-and-trade with the Pistons. They gave up a 2023 first-round pick and some cash, which seemed reasonable for a sharpshooter like Kennard. He shot over 44% from three-point range that season, and as a fan of teams that prioritize spacing, I loved this move. It’s one of those deals where you just go with the flow, trusting the front office’s vision. But not every team had that luxury. The Houston Rockets, for instance, traded Russell Westbrook to the Wizards for John Wall and a first-round pick. On paper, it might have looked like a fresh start, but Wall’s injury history and Westbrook’s resurgence in Washington made this a clear loss for Houston. Wall only played 40 games that season, averaging 20.6 points, but his efficiency dipped, and the Rockets ended up in a rebuild. I’ve always been skeptical of trades centered on aging stars—it’s like betting on a horse with a limp, and in this case, Houston paid the price.

Another deal that caught my eye was the Philadelphia 76ers trading Al Horford to the Thunder. They offloaded his massive contract and got back Danny Green and Terrance Ferguson. Horford was a mismatch in Philly, averaging just 11.9 points and 6.8 rebounds, and his fit alongside Joel Embiid was clunky at best. As an analyst, I’ve seen how poor roster construction can derail a team, and this move felt like a correction. Green’s three-and-D role helped space the floor, and the Sixers improved their playoff run. Meanwhile, the Thunder were clearly in asset-collection mode, but taking on Horford’s deal without immediate returns felt like a short-term loss—though their long-game might pay off. It’s a reminder that in the NBA, sometimes you have to ride the system, even if it means swallowing a bitter pill for future gains.

Let’s not forget the smaller moves, like the Denver Nuggets acquiring Aaron Gordon from the Magic. They gave up Gary Harris, R.J. Hampton, and a first-round pick, and Gordon’s athleticism and defense seamlessly fit alongside Nikola Jokić. I recall watching their playoff games and thinking how this trade elevated Denver from a good team to a contender. Gordon averaged 10.2 points and 4.7 rebounds, but his intangibles were huge. In contrast, the Orlando Magic seemed to be in perpetual rebuild, and while they got young pieces, they haven’t made significant strides since. From my perspective, trades like this highlight the importance of fit over raw talent—a lesson some GMs still overlook.

Wrapping up, the 2020 trade season was a mixed bag, with teams like the Bucks and Nuggets emerging as big winners by making bold, system-fitting moves. Others, like the Rockets, got caught in reactive deals that set them back. As I reflect, that idea of "going with the flow" resonates—success often comes from adapting to opportunities, not just accumulating assets. Personally, I lean toward trades that build chemistry over star power, and the data (even if rough around the edges) supports that. For instance, the Bucks’ championship and the Nuggets’ deep runs weren’t flukes; they were built on smart, timely deals. In the end, the biggest losers were those who failed to read the system, proving that in the NBA, you either ride the wave or get swept away.