Editor’s note: The following is an excerpt from Bill Simmons’s book The Book of Basketball: The NBA According to The Sports Guy, copyright 2010 by Bill Simmons. Reprinted with permission of ESPN Books, an imprint of ESPN, Inc., New York, and Ballantine Books, an imprint of The Random House Publishing Group, a division of Random House, Inc., New York.

In honor of the 50th anniversary of Oscar Robertson’s 1961-62 season, where he averaged the first, and only, triple double in league history, here are two excerpts from Bill Simmons’s book The Book of Basketball. The first entry deals with Robertson’s placement in Simmons’s Basketball Hall of Fame concept. The second breaks down why Robertson’s legendary season shouldn’t be as highly regarded as it is.

10. OSCAR ROBERTSON

Resume: 14 years, 13 quality, 12 All-Stars ’64 MVP ’61 Rookie of the Year Top 5 (’61, ’62, ’63, ’64, ’65, ’67, ’68, ’69), Top 10 (’70, ’71) 3 All-Star MVPs 5-year peak: 30-10-11 (first 5 seasons) 2-year Playoffs peak: 31-11-9, 47.2 MPG (22 g’s) leader: assists (6x), FT% (2x) career: 25.5 PPG (8th), 9.5 APG (3rd), 7.5 RPG, FT’s (3rd), assists (4th), points (10th) 2nd- best player on champ (’71 Bucks), starter on runner-up (’74 Bucks) 25K Point Club

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Back in February 2008, I was killing time in an airline club waiting for my delayed flight to board. Sitting only twenty feet away? NBA legend Oscar Robertson. Did I jump at the chance to make small talk with one of the ten greatest players who ever lived? Did I say to myself, “This is a gift from God, I can introduce myself to Oscar, tell him about my book, maybe even have him help me figure some Pyramid stuff out”? Did I even say, “Screw it, I gotta shake his hand”?

Nope. I never approached him.

Had I heard too many stories about Oscar being a miserable crank? Was I still scarred from finishing his 2003 autobiography, The Big O: My Life, My Times, My Game, maybe the angriest, most self-congratulatory basketball book ever written by anyone not named “Wilt”? Did I feel bad because Oscar was a profoundly bitter product of everything that happened to him? I don’t know. But he may as well have been wearing a BEWARE OF OSCAR sign. And so we killed time just twenty feet apart for the next three hours. I never said a word to him.

There are few happy Oscar stories. Teammates lived in perpetual fear of letting him down. Coaches struggled to reach him and ultimately left him alone. Referees dreaded calling his games, knowing they couldn’t toss the league’s best all-around player even as he was serenading them with F-bombs. Fans struggled to connect with a prodigy who had little interest in connecting with them. After he finished in the top five for assists and points for nine straight years, made nine straight first-team All-NBA appearances, averaged a triple double for the first five years of his career, won the ’64 MVP with Russell and Wilt in their primes and transformed the role of guards in professional basketball, his team still decided, “We need to get rid of him.” Even his hometown paper (the Cincinnati Enquirer) piled on by writing in February 1970, “For years, Oscar has privately scorned the Royals management; he has ridiculed Cincinnati and its fans; he has knocked other players, both on his team and others; and he has never been willing to pay a compliment. He is, has been and probably will grow old a bitter man, convinced that it was all a plot.” Of course, Oscar included this excerpt in his book thirty years later as proof that the notoriously right-wing newspaper was bigoted. Maybe both sides were right.

Oscar grew up like Bizarro Jimmy Chitwood in Bizarro Hoosiers, the never-released movie where a black basketball team prevailed but not before facing profound prejudice and hostility along the way. When Oscar’s Crispus Attucks High School became the first all-black champion in state history in 1955, Indianapolis rerouted its annual championship parade toward the ghetto, with the implication being, We don’t trust the blacks to behave themselves, so let’s keep this self-contained. Oscar never got over it. Nor did he get over Indiana University’s coach, Branch McCracken, for recruiting him by saying, “I hope you’re not the kind of kid who wants money to go to school.” (Note: If you don’t think Oscar didn’t immediately stand up and walk out of the room, then you don’t know Oscar well enough. Yes, that was a triple negative. I was due.) He chose the University of Cincinnati and had experiences that defy imagination six decades later. This stuff actually happened? His teachers belittled him in class and went out of their way to make him feel dumb. In Dallas, fans greeted him by tossing a black cat into his locker room. In Houston, he couldn’t check into his hotel because of a NO BLACKS ALLOWED sign only his team stayed there anyway, with poor Oscar stuck sleeping in a Texas Southern dorm room. In North Carolina, someone delivered him a pregame letter from the Grand Wizard of the Ku Klux Klan that simply read, “Don’t ever come to the South.” In St. Louis, he and a black teammate strolled into a restaurant and were greeted by stony silence, followed by every other customer clearing out within a minute or two. Even in downtown Cincinnati, they had “colored” water fountains and a cinema that wouldn’t allow blacks as patrons a theater that stood only half a block from where he starred for the Bearcats. Night after night, Oscar was filling a gym with fans and couldn’t even walk down the street to catch a movie.

At some point, the Big O snapped, shut himself off and settled for taking his frustrations out on everyone else. I don’t blame him one iota — even in photos of Oscar from high school to the NBA, you can actually see the grim transformation in his face. Young Oscar is wide-eyed, innocent, grinning happily in every photo. Older Oscar looks like he’s smoldering, like he’s barely happy enough to fake a smile for the photographer. Had Magic or Jordan dealt with everything Oscar dealt with, they would not rank higher than him in this book. There’s no way. So in a Pyramid that hinges on five dynamics — individual brilliance, respect from peers, the statistical fruits/spoils of whatever era, team success and an intangible connection with teammates — Oscar’s career remains the toughest to project. Yes, he was brilliant. Yes, his opponents and teammates revered him. Yes, he took advantage of some undeniable gifts from his particular era. No, his teams didn’t succeed as much as you’d think. No, his teammates didn’t love playing with him (as much as they respected him). His statistics were remarkable, sure, but didn’t we just spend a book that’s now the size of War and Peace proving that basketball is more than just numbers? Shouldn’t it matter that Oscar never made the Finals until his eleventh season, well after his prime, when he rode Kareem’s gangly body to his first title? Or that Oscar thrived statistically but missed four postseasons and only won two playoffs total? Or that three former teammates went on the record with the following quotes (from Tall Tales)?

Jerry Lucas: “Oscar was a perfectionist and he’d yell at you if you messed up. Then you saw that he yelled at everyone, so you learned not to take it personally.”

Zelmo Beaty: “He was such a perfectionist that I never could have lived up to his expectations. The way he’d scream at Wayne Embry: ‘You dummy, catch the ball I put the ball right in your hands, how could you drop that one?’ I felt sorry for Wayne.”

Wayne Embry: “Oscar was so far ahead of us humans that you could never come up to his level. But because of his greatness and what he meant to the franchise, you hated to fail him. Oscar’s greatness sometimes overwhelmed Adrian Smith. [He’d] tell Oscar, ‘Please, O, you know I’m trying, I really am. You gotta believe me, O.’ ”

Oscar’s demanding personality overwhelmed everyone around him. After his playing career ended and CBS jettisoned him in 1975, nobody hired him as a coach, general manager, broadcaster, or adviser for the next thirty-four years (and counting). He resurfaced occasionally as the Grumpy Old Superstar in any story comparing the good old days to whatever was happening in the current era. You could always rely on one churlish Oscar quote about how today’s players make too much money; how he never could have palmed the ball so blatantly back in his day; how he would have loved to have played in an era of charter planes, personal trainers and low expectations; how today’s triple doubles didn’t matter because you could get an assist for anything nowadays. Every Oscar quote makes it sound like Dana Carvey should be playing him with Robert Downey Jr.’s Tropic Thunder makeup. Back in my day, I used to get triple doubles playing in bad sneakers with nails sticking out of the floor and fans throwing stuff at me and I loved it! There’s just enough evidence that Oscar was an insufferable curmudgeon that he vacillated as high as no. 6 and as low as no. 12 for my Pantheon over a three-month span, ultimately settling here.

We know this much: every teammate and opponent revered his talents; the consensus seems to be “Jordan before Jordan”; and even West admits that it took him three or four years just to catch up to Oscar’s level. But since every laudatory Oscar story centers around his uncanny consistency and not quotes like “nobody was better when it mattered” and “this guy could turn chicken shit into chicken salad,” how can we reconcile his phenomenal individual success with his undeniable lack of team success? His supporting cast was serviceable from 1961 to 1966 (Lucas, Twyman, Embry, and ’66 All-Star MVP Adrian Smith were his four best teammates); you could argue his teams slightly overachieved by finishing 60 games over .500, going 55-25 in ’64 and dragging two Russell teams to a deciding playoff game. On the flip side, he played with quality players from ’67 to ’70 — not just Lucas and Smith, but youngsters who went on to bigger and better things, like Jon McGlocklin, Bob Love, Happy Hairston, and Tom Van Arsdale — and never dominated an increasingly diluted league. Considering Jordan’s supporting cast was equally uninspired and his league was tougher, it’s hard to fathom why Jordan’s teams kept improving while Oscar’s teams wilted over time. Both were famously brutal with teammates, only Jordan’s competitiveness boosted his team’s collective confidence while Oscar chipped away at it. Can you succeed when you’re petrified of letting your best guy down? Beyond that, can you succeed when your best scorer also happens to be the guy running your team? Obviously not. The Royals never won anything and really, never did anyone else who fit that category.

The bigger problem is that Oscar’s top-ten resume rests mostly on one thing: his dominance from 1961 to 1965, when he averaged a triple double and unleashed holy hell from the guard position. Those numbers make more sense than you’d think. Much like Wilt, Oscar was four or five years ahead of his time from a physical standpoint. There were only four “modern” guards during Oscar’s rookie season; since the other three (Sam Jones, Greer, and West) were shooting guards, Oscar physically overpowered defenders the same way that Wilt boned up on the Darrell Imhoffs and Walt Bellamys. Imagine if 2009 Dwyane Wade played against a steady stream of Jason Terrys and Steve Blakes every night for 70 games, and for the other 12 he had to play against Kobe and Pierce. Then imagine every power forward was six foot six and under, and imagine there were only seven elite centers in a thirty-team league. Next, imagine he played in a run-and-gun era where there were 80 rebounds and 120 field goal attempts available every game.Would Wade average a 35-10-10 for the season? Of course he would. How is that different from Oscar’s situation as a rookie? There were eight teams and eighty-eight players total, along with an unwritten “don’t have more than two black guys on your roster” rule. So in a peculiar twist, some of Oscar’s early success happened because of racism. Unleashing Oscar on a mostly white NBA in 1960 was like unleashing a horny Madonna on a nightclub filled with good-looking twenty-year-old Hispanic dancers. Check out the cream of the crop for Oscar’s first season.

1961 All-Stars (guards): Oscar and Greer (black); West, Cousy, Tom Gola, Gene Shue, Larry Costello, Hot Rod Hundley, Richie Guerin (white)

1961 assist leaders (guards in top twenty): Oscar, Guy Rodgers (black); West, Cousy, Gola, Shue, Costello, Hundley, Guerin, Johnny McCarthy, Bucky Bockhorn, Chuck Noble (white)

KC Jones, Al Attles and West were Oscar’s only opponents who could dream of handling him physically. Oscar used his size with scorching results, backing smaller players down, finding his favorite spots 15 feet from the hoop, then turning around and shooting over whomever. The Big O mastered a deadly high-post game that hadn’t even been invented yet — like watching a Wild West duel where one guy pulls out a revolver and the other guy pulls out an Uzi. Within five years, the color of the league changed, the pace of the games slowed and Oscar lost that Uzi/revolver advantage to some degree.

1966 All-Stars (guards): Oscar, Greer, Rodgers, Sam Jones, Eddie Miles (black); West, Ohl, Adrian Smith (white)

1966 assist leaders (guards in top twenty): Oscar, Rodgers, Wilkens, Greer, Mahdi Abdul-Rahman, Dick Barnett, Wali Jones, Sam Jones (black); West, Guerin, Ohl, Adrian Smith, Kevin Loughery, Howard Komives, Johnny Egan (white)

Is that why Oscar’s stats dropped slightly (28-6-10 from ’66-’70) when he should have been peaking like West? The Royals never won a playoff series after 1965; from 1968 to 1970, they missed the postseason completely as Oscar gained weight and said things like “My primary purpose is to get the team moving, establish community out there and make some money.” There was no magic in his game, just a quality that Frank Deford described in 1968 as “eerily consistent,” adding, “In eight years as a pro he has never averaged less than 28.3 points a game or more than 31.4, and in six of the eight years his average varied less than a point. In assists and free throws he has maintained the same level of consistency. He is like a .333 hitter who arrived at that figure by going 1 for 3 with one walk in every game of the season.” Instead of Mr. Clutch, Oscar was Mr. Groundhog Day. That went for his personality, too. He grumbled about being underpaid and marginalized so relentlessly that the Royals swapped him for Gus Johnson, only Oscar pushed for a $700K extension from Baltimore before vetoing the trade. (Before you excuse his behavior by saying, “The guy was frustrated, he just wanted to win,” consider Magic Johnson’s plight late in his career. He was saddled with Kareem’s corpse in ’89, a Mychal Thompson/Vlade Divac center combo in ’90, then a Divac/Sam Perkins combo in ’91. His best teammate was Worthy, an excellent player who couldn’t crack my top forty-five. His second-best teammate was Byron Scott, never an All-Star and a textbook “right time, right place guy.” In a loaded league, did Magic give up, point fingers or demand a trade? Nope. He averaged 59 wins per year and dragged the Lakers to two Finals.) When the Royals shipped Oscar to Milwaukee, I know it’s romantic to think, “They just wanted to give him a chance at a ring.” Here’s the reality: Cousy decided Oscar wasn’t worth big money anymore and sent him packing for 40 cents on the dollar, then tabbed Tiny Archibald to replace him. The following players would never have been traded unless they demanded out: Bird, Magic, Jordan, West, Duncan, Shaq, Hakeem or Russell. In Oscar’s case, the Royals moved in a different direction. Big difference.

Clearly, something was a little off with the Big O. You never heard the word “happy” with him, except for that transcendent ’71 season when the Bucks destroyed everyone in their path. He ended up leaving Milwaukee just as unhappily as he’d left Cincinnati, furious that the team lowballed him (in Oscar’s mind) before the ’75 season. Sam Goldpaper’s subsequent New York Times story started, “Pro basketball has lost what once was its greatest and most complete player. Oscar Robertson, after 14 seasons and many contract disputes, announced his retirement last night.” You couldn’t get through the second sentence of Oscar’s basketball obituary without finding something negative. Twenty-eight years later, Jack McCallum’s SI feature wondering why Oscar had effectively disappeared from basketball started, “The Big O is known in basketball circles for being the Big Grind, a hoops curmudgeon who protests that in his day the players were better, the coaches smarter, the ball rounder. The reputation is not entirely undeserved. But today — 40 years after a season in which he averaged a triple double in points, rebounds and assists — Oscar Robertson wants you to know that he does not spend his hours stewing in a kettle of his own bile. Well, wants you to know is a little strong because, frankly, he doesn’t much care what you think.”

Again, complimentary but negative. Nobody sifted through Oscar’s never-ending acrimony well enough to figure him out. Even when he heroically donated a kidney to his ailing daughter in 1997 (saving her life), the moment came and went; you probably didn’t remember until I reminded you. His biggest legacy had nothing to do with talent: Oscar’s ballsy performance as president of the Players Association led to skyrocketing contracts, the ABA/NBA merger, an overhaul of free agency and every eight-figure deal we see today, only he never gets credit because the struggles of NBA players haven’t been romanticized by writers or documentarians. Even stranger, of all the NBA legends who ever lived, only Oscar doesn’t belong to a current franchise because the Royals moved to Kansas City in 1973 (and then Sacramento in 1985). He can’t go back home like Russell/Bird in Boston, or Magic/West/Kareem in Los Angeles, or even Willis/Clyde/Ewing in New York, simply because home doesn’t exist. He’s a historical nomad. He belongs to nobody. And maybe it’s better that way. To this day, Oscar remains damaged goods — a victim of his vile racial climate, someone who battled a rare form of post-traumatic stress disorder that can’t be defined. As his teammate during Oscar’s prime, you would have respected the hell out of him, you would have felt sorry for him, you would have marveled at him but ultimately, I’m not sure you would have enjoyed playing with him that much. This was a man who decided during the epilogue of his book, “Once I heard someone say that in order to write love songs, you have to have been through some bad times. To write a love song, you had to have your heart broken. If that’s the case, I can state right here and now that I could write the greatest songs in the world.”

Of all the injuries that determined the ninety-six spots of my Pyramid, I can tell you this much: Oscar Robertson’s broken heart resonates the most.

• For the second excerpt, CLICK HERE