Bill Simmons Ranks Russell Westbrook Only 10th Among The Best Guards Of The Last 20 Years

Bill Simmons praised Russell Westbrook's unmatched athletic dominance but still ranked nine guards ahead of him based on their overall peaks.

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Mandatory Credit: Alonzo Adams-USA TODAY Sports

Russell Westbrook, who retired recently, was one of the most explosive guards in NBA history, arguably the most explosive ever, but Bill Simmons still believes there are nine guards in the last 20 years who had better peaks.

On his podcast, Simmons praised Russell Westbrook’s athletic dominance before placing him 10th on the list of guards over the past two decades.

“In my lifetime, I have seen only four other basketball players turn one-on-three fast breaks into layups whenever they wanted. Young Barkley, young Derrick Rose, Jordan, and LeBron. Now Russ would be the fifth. Russ would be like, ‘I’m f**king going. You better get out of my way, or you’re taking a knee in your chest.'”

At his peak, Westbrook really was that overwhelming. The defining season came in 2016-17, when he averaged 31.6 points, 10.7 rebounds, and 10.4 assists and became the first player since Oscar Robertson to average a triple-double across an entire season.

Westbrook won the MVP award that season and eventually averaged a triple-double four times during his career.

But when Simmons shifted from athleticism to overall peak value and winning, Westbrook began sliding down the rankings.

“Peak guards, last 20 years, just talking about peaks: Curry, Kobe, Wade, SGA, Harden. There’s five that were better than Russ. CP3, Nash, Brunson. Do you consider Luka a guard? That’s nine. Russ is probably 10th. I don’t think I missed anyone I went through, but peak Russ, I think, was one of the 10 best guards of the last 20 years, but I think he’s 10th.”

“All nine of those guys, I think, could have been the best guy on a title team or close, right? And I’m not sure Russ could have. Russ never won a playoff series after KD left as the best guy. So I think that’s a fair list.”

Simmons’ list creates a top 10 of Stephen Curry, Kobe Bryant, Dwyane Wade, Shai Gilgeous-Alexander, James Harden, Chris Paul, Steve Nash, Jalen Brunson, Luka Doncic, and Westbrook.

The most debatable names are probably Jalen Brunson and SGA because their peaks came much later compared to Westbrook’s longer resume.

Westbrook was an MVP, a nine-time All-Star, a nine-time All-NBA selection, a two-time scoring champion, and a three-time assist leader. But Simmons was not ranking careers. He was ranking peaks, specifically whether each player could be the leading star on a championship-winning team.

And that’s where Westbrook’s postseason resume turns against him. After Kevin Durant left Oklahoma City, Westbrook’s playoff series record stood at 2-7. His only two playoff series victories came when he was part of the Houston Rockets in 2020 and the Denver Nuggets in 2025.

Apart from that, the Thunder suffered three consecutive first-round exits with Westbrook as the best player from 2017 to 2019. When he reached the second round with Houston in 2020, James Harden was the best player. And when he reached the second round in 2025, Nikola Jokic and Jamal Murray were above him in the pecking order.

But this doesn’t mean that Simmons was simply dismissing Westbrook’s greatness. Placing Westbrook alongside Michael Jordan, LeBron James, Charles Barkley, and Derrick Rose as one of the most unstoppable transition players is Simmons giving him massive praise.

If it’s athletic dominance and sheer force, Westbrook has an argument against almost everyone. If it’s championship-level decision-making and being an unquestioned number one option on a title-winning team, Simmons thinks there are nine guards from the last 20 years who peaked higher.

And for him, that is why Westbrook lands exactly at No. 10.

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Vishwesha Kumar is a staff writer for Fadeaway World from Bengaluru, India. Graduating with a Bachelor of Technology from PES University in 2020, Vishwesha leverages his analytical skills to enhance his sports journalism, particularly in basketball. His experience includes writing over 3,000 articles across respected publications such as Essentially Sports and Sportskeeda, which have established him as a prolific figure in the sports writing community. Vishwesha’s love for basketball was ignited by watching LeBron James, inspiring him to delve deeply into the nuances of the game. This personal passion translates into his writing, allowing him to connect with readers through relatable narratives and insightful analyses. He holds a unique and controversial opinion that Russell Westbrook is often underrated rather than overrated. Despite Westbrook's flaws, Vishwesha believes that his triple-double achievements and relentless athleticism are often downplayed, making him one of the most unique and electrifying players in NBA history, even if his style of play can sometimes be polarizing. 
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