Along with Stephen A. Smith, Skip Bayless' work fronting First Take made him front and centre of ESPN's coverage for a number of years. Not afraid to voice his opinion, even when he is in the minority, Bayless' numerous controversial takes made him an absolute must-watch for basketball fans.
Following his exit from ESPN, Bayless picked up work with Fox Sports in September 2016, and worked with the network on its Undisputed show until he left in August 2024. While he might be out of the television eye now, Bayless remains a well-known figure in the basketball world, and hasn't shied away from giving his take on all things NBA-related.
Speaking on the All The Smoke podcast with Matt Barnes and Stephen Jackson, Bayless delivered his verdict on the NBA's GOAT debate, and he wasn't scared of making some very controversial choices. And, when compared to the greatest basketball players of all-time list his old sparring partner Smith delivered, it's night and day.
10 Wilt Chamberlain
One of the most dominant players to ever play the game, Wilt Chamberlain shattered records left, right and centre during his time in the NBA. The behemoth was a points and rebounding machine, and remains the only player in history to notch 100 points in a single game. His rivalry with the Bill Russell and the Boston Celtics was legendary, and while he might not have come out on top during those contests, he was still feared up and down the association.
9 LeBron James
Arguably the most controversial ranking choice on Bayless' list, the former ESPN analyst has LeBron James down as the ninth greatest basketball player of all-time, despite the majority of fans seemingly having him battle with Michael Jordan for the no.1 GOAT spot. Despite Bayless' own views, James' resume speaks for itself, being a multiple-time MVP and champion, while his longevity and still being able to play at the highest level counts considerably in his favour too.
Before 40,000 points I had LeBron 9th on my All-Time list. After 40,000 points, I still have LeBron 9th on my all-time list. Playing longer does not make you better or more valuable.
LeBron James is not better than Larry Bird, he's not better than Kobe Bryant... both Bird and Bryant were better shooters and much, much better closers than LeBron James.
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8 Larry Bird
One of the greatest Boston Celtics players of all-time, Larry Bird was the ultimate winner, combining IQ and skill to become one of the most devastating players in the 1980s. Capable of shooting from beyond-the-arc - and arguably being one of the first to really effectively do so - Bird could drive to the paint, finish and also pass when needed too.
I rank LeBron all time at #9. #8 on my list is Larry Bird. Larry Bird was just a little better than LeBron James has been through almost 17 years. Killer will, mental toughness, clutch gene — Larry Bird was a bad man.
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A genuine two-way player, Bird could do it all, and his multiple MVP awards speak to that. It was his rivalry with Magic Johnson and the Los Angeles Lakers that really caught the eyes of basketball fans around the world, and the two's superstar quality made it just that much more interesting to watch.
7 Kobe Bryant
In a franchise that has seen multiple Hall of Fame players come and go, Kobe Bryant goes down as one of the greatest Los Angeles Lakers stars of all-time. The man who lived by the 'Mamba Mentality' was a part of one of the most dominant duos in NBA history alongside Shaquille O'Neal, and while the latter may have won the Finals MVP award during those early championship reigns, Bryant was beginning to come into his own.
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The shooting guard eventually saw his hard work all pay off by winning two titles without O'Neal, and winning the Finals MVP award in the process both times too. A supreme scorer who didn't let one bad shot affect him from taking another, Bryant's mentality and relentless will to win is perhaps only matched by one other man in NBA history.
6 Bill Russell
A multiple-time NBA champion, who along with Wilt Chamberlain, posted obscene numbers from the center position, Boston Celtics legend Bill Russell is the very definition of greatness. A winner of the NBA's Most Valuable Player award a remarkable five times - including for three years in a row between 1961 and 1963 - the 6 foot 10 star led the league in rebounding on four occasions, and was named to the NBA's 25th, 35th, 50th and 75th anniversary teams.
In the history of basketball, perhaps there has never been anyone who impacted things off-the-court just as much as he did on it. Russell's legacy and importance to the game and for the players who came after him cannot be understated.
This man revolutionized how to play professional basketball. He became the most unselfish superstar I have ever seen and it's not even close.
5 Tim Duncan
It speaks to Tim Duncan's greatness, that his five championships with the San Antonio Spurs came in three decades. Having won his first title in 1999, he would win three more in the 2000s (2003, 2005, 2007), before picking up his final one in 2014. Back-to-back MVPs came his way in 2002 and 2003, while of the 15 times he was selected to an All-NBA team, 10 of them were for the First-Team.
Duncan's legacy is that many of his peers regard him as the greatest power forward of all-time, with the 'Big Fundamental' an elite defender, rebounder and scorer from the post.
4 Kareem Abdul-Jabbar
Before Michael Jordan and LeBron James came onto the scene, there is certainly a legitimate argument to be made that Kareem Abdul-Jabbar was the greatest player in NBA history. His unstoppable sky-hook shot is still talked about to this day, while his longevity in playing with the Milwaukee Bucks and Los Angeles Lakers is a testament to his professionalism, ability and work ethic.
He would become the league's all-time leading scorer - a record only broken by LeBron James - and remains one of the best centers to ever play the game.
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3 Shaquille O'Neal
Skip Bayless holds Shaquille O'Neal in such high regard, that he counts him as the third greatest basketball player of all-time. O'Neal arguably goes down as the most dominant player in NBA history, with his sheer power and strength seeing him bully opposition players into submission.
A freak athlete and a rather underrated passer out of the post, O'Neal's run in the Los Angeles Lakers' extraordinary success at the turn of the century goes down in history. Aside from his one MVP award in 2000 (although he thinks he should have won more later down the line), O'Neal also won the Finals MVP award in each of the Lakers' title victories from 2000 to 2002.
In all my years of watching and studying the National Basketball Association, I’ve never seen anything like Shaquille O’Neal for 2000, 2001, 2002 and maybe even 2003. It was the most overpowering force imaginable. He was unguardable, unstoppable, un-refereeable.
2 Magic Johnson
Simply put, the greatest point guard of all-time. Magic Johnson redefined what it was to play the position, with his combination of size and passing making him virtually unmatched in his era. A three-time MVP, Magic would lead the league in assists four times, while he also showed his defensive prowess by topping the charts for steals on two occasions too at the beginning of the 1980s.
Finishing his career averaging just short of 20 points but with over 10 assists a game to his name, Johnson was crucial to the Los Angeles Lakers' success during the latter part of the 20th century.
1 Michael Jordan
The undisputed greatest of all-time, Michael Jordan remains to this day the ultimate basketball superstar. The shooting guard transcended the sport, with his Air Jordan brand and ventures into Hollywood with movies like Space Jam simply underlining just how far ahead he was of everyone when it came to popularity.
The face of the league during the 1990s, Jordan's record in NBA finals is second-to-none, winning all six he was in. One of the best defenders in NBA history too, Jordan's two-way greatness is perhaps another reason why observers point to him being the GOAT over the likes of LeBron James for example. Despite some of his controversial takes earlier on this list, Skip Bayless concurs with the majority, by naming Jordan as the greatest basketball player of all-time.