The Three Oscars


The acceptance speeches from last night’s show are finally over, and Matthew McConaughey is surely still elbow deep in champagne.  Every year, the Oscars are a breeding ground for judgments to be cast from every direction, focusing on the movies themselves to the red carpet cameos to the host’s good-natured barbs.  The affair pulsates with arguments about overratedness and underratedness — who should have won, who lobbied the hardest for an undeserved award, and who was belatedly gilded for unrelated performances in decades past.  It turns out Oscar is an important name in the sports world as well, and has produced several of the most wildly underrated and misjudged athletes of all time.  It is worth telling the story of three notables in particular, each an all-time great in his sport and each in need of a bit of clarification:  Oscar Charleston, Oscar Robertson, and Oscar De La Hoya. 

For a name that has never been in the top 50 U.S. baby boy names since 1900, “Oscar” sure has produced some indelible sports figures.  In addition to the three subjects of this article, a quick shout out is warranted to rising Chelsea and Brazil national team soccer standout Oscar, who has already garnered attention as a world-class talent, and South African double amputee sprinter and Paralympic gold medalist and legend Oscar Pistorius, whose trial for the shooting death of his girlfriend, Reeva Steenkamp, will begin in Johannesburg this month.Finally, I would be remiss if I did not mention baseball’s Oscar Gamble,2 a journeyman outfielder and designated hitter in the 70’s and 80’s, who gave us the classic mind- and verb-bending quote about the prevalence of racism in the major leagues:

“They don’t think it be like it is, but it do.”

All three of our all-timer Oscars have had a strange and uncharacteristic relationship with media, fame, and legacy, each of a different nature.  Let’s explore each one.

Oscar Charleston:

Given the rich history of baseball and the fame of its top stars, it is strange that perhaps the best baseball player who ever lived remains so unknown.  Oscar Charleston’s strange relationship with fame and legacy is simple: he was, is, and probably always will be criminally underrated.


We know he was born in 1896, served in the military at a young age, and then began his nearly four-decade long baseball career as a sprightly outfielder with the Indianapolis ABCs in 1915.  This was several years before the creation of the first Negro National League, but by the time 1920 rolled around, the Indianapolis team entered the league as a charter member with Charleston having already established himself as a top player.  During those early years of the organized Negro National League, Charleston was by far its biggest star, hitting for uncommon power and also, at times, batting for an absurdly high average (in 1921, he topped the league by hitting somewhere between .434 and .446 while leading his league in many other wide-ranging categories, including doubles, triples, home runs, and stolen bases).  Charleston was an undeniable all-around combo star.  He was stocky and barrel-chested, but also shockingly fast on the basepaths and in center field.  Indeed, many say that his defensive speed revolutionized how others began to play center field.  He was intense and aggressive, and piled up numbers like no other man of his or any era.

In 1922, he moved to the Eastern Colored League and played for the Harrisburg Giants, the Hilldale club of Darby, Pennsylvania, and the Homestead Grays for the better part of a decade, all the while serving as his team’s manager as well.  He hit at least .350 through this entire period, and topped out over .400 at least twice.  He maintained nearly the same absurd level of success in the mid-1930’s with the Pittsburgh Crawfords, where he crossed paths with legendary slugger Josh Gibson for a period of time.  He retired from playing and managed the Philadelphia Stars in the early 1940’s, and helmed Branch Rickey’s Brooklyn Brown Dodgers in the U.S. League in 1945.  Once the Major Leagues integrated in the late 40’s, the U.S. League disbanded and Charleston managed the Indianapolis Clowns of the Negro American League until 1954, when he died following a heart attack and stroke at age 57.

His talents have been described as a cross between Ty Cobb, Babe Ruth, and Tris Speaker, three of the game’s absolute Pantheon greats.  When Willie Mays came on the scene in 1951, his skills were compared to Charleston’s.  He led his teams to various championships as early as 1916 and as late as 1935.  He appeared in numerous East-West All-Star games in the 30’s.  He is among the top five in Negro Leagues history in both home runs and batting average.  He is the career stolen bases leader among Negro Leagues players.  Beyond his popularity among fans, which was extensive, Charleston enjoys one of the most pristine reputations among fellow baseball players and greats of his era, both for his spectacular exploits on the field and his exemplary tutelage as a manager.  Knowledgeable colleagues and sophisticated baseball writers have placed him at or near the top of the all-time heap — Bill James, for example, listed Charleston as the fourth best player ever, behind only Ruth, Honus Wagner, and Mays.  Many Negro Leagues experts consider him to have been the best Negro Leagues player of all time.


It remains a sad truth that he has, in many ways, slipped through the cracks of the public’s consciousness.  Part of the reason he has enjoyed far less fame than his white contemporaries, and even much less than other Negro Leagues legends like Satchel Paige and Gibson, is probably simply the era he played in.  He pre-dated Paige and much of Gibson, and very little multimedia of any kind exists to showcase his ballplaying prowess.  Another reason is that he played all over the Midwest (Indianapolis, St. Louis, Harrisburg, Darby, Pittsburgh, Toledo…) but spent only bits of his career in major eastern cities.  He also had a fierce personality that, while perfectly suited to his style of play, probably alienated some onlookers and caused them to gravitate to more convivial stars like Paige.  The “white” press glommed onto Paige in a way that it never had for Charleston, and his imprint on the country’s collective baseball memory was much more faint than Paige’s as a result.

Regardless, he is our first Oscar to have had a strange relationship with legacy and legend.  For reasons that surely aren’t good enough, whatever they are, Charleston was not inducted into the Baseball Hall of Fame alongside several of his other Negro Leagues legends in the early 70’s, but was instead inducted in 1976.

Oscar Robertson:

Oscar Robertson’s accomplishments on the basketball court are is-that-a-misprint ridiculous.  As a three-year college player at the University of Cincinnati, he was a three-time All American, a three-time Player of the Year, a three-time national scoring champion, and he set 14 different NCAA records.


He was NBA Rookie of the Year in 1961.  He was the NBA MVP in 1963-64, and he probably should have been the next year as well, when he led the league in Win Shares.3  He made 11 All-NBA Teams, including nine straight All-NBA First Teams (1961-69) and two Second Teams (1970-71).  He played in 12 consecutive All-Star Games from 1961-72, and was MVP of three of them.  He helped lead the Milwaukee Bucks to their only championship in 1971.  He had his number retired by three different teams (University of Cincinnati, Cincinnati Royals/Sacramento Kings, and the Bucks).  He was versatile enough to score 26,000+ points and also lead the NBA in assists six different times, while leading the league in free throw percentage twice for good measure.  Watch his highlights and you see a classic example of a player who is too brawny and powerful for guards and too quick for frontcourt players:

He famously averaged a triple double for an entire season in 1962, and still remains the only man to accomplish the feat.  Less known is the fact that he very nearly accomplished the feat for the first five years of his career.  In doing so, he never averaged below 9 rebounds or 9.5 assists.  The numbers are damn near cartoonish.  See for yourself:

The (VERY) Big O
























He compiled as unique an NBA resume as anyone ever.  Well, this side of Sam Bowie.  Fans on the Elo Rater rank him third best of all time, ahead of Michael Jordan.  The man was an absolute stud colossus.  So why is he rarely mentioned in discussions of basketball’s Mount Rushmore, and why hasn’t he enjoyed the same kind of mythic cultural prestige of Wilt Chamberlain and Jerry West?

Any story of The Big O is incomplete without highlighting his early playing days in high school, at the segregated all-black Crispus Attucks High School in Indianapolis.  With Robertson, the team became highly competitive and challenged for the state title in 1954, losing in the quarterfinals to the rural upstart team from Milan, Indiana, on whom “Hoosiers” was based.  The following year, Robertson lowered the boom and led the team to the first state championship by an all-black team in the country.  The following year, his squad duplicated the feat, this time going undefeated.  The exploits of his team were met with mostly racist angst in and around Indianapolis, and he was the target of racial slurs.  It is easy to see why and how he hardened his attitude and fashioned his well-known prickliness in the face of such cultural conditions, as his team was barred from “white” restaurants and generally mistreated.  His reputation as a cross and/or nasty individual was probably somewhat based in reality, as Robertson surely harbored anger toward the racially tinged social patterns he faced on a daily basis.  But he remains a very articulate and thoughtful man, and the fact that he had confrontations with many NBA types in his day is no justification for dampening his otherwise blindingly bright legacy.  And to complete the 2014 Oscars loop, he looked a hell of a lot like Best Actor nominee Chiwitel Ejiofor:


Beyond blazing trails on the court and in the cultural zeitgeist, Robertson was also a pioneer in the business of basketball, and is one of the large figures in NBA union history and in the creation of modern free agency.  As head of the Players Association, he spearheaded an antitrust suit to combat players being forbidden to talk to other clubs once their contract was up, among other things.  After years of litigation, the case’s ripples were felt in increased free agent signings and higher player salaries.

Robertson himself has named Elgin Baylor as the most neglected NBA star, but few would argue with Oscar himself as the best candidate.  He blazed a stunning trail for the large guards of the modern game, including Magic Johnson, Penny Hardaway, Steve Smith, Jalen Rose, and many others, and he set a blistering statistical pace that has never been threatened.  When asked whether LeBron James or Michael Jordan is better, Kareem Abdul-Jabbar answered that Robertson “would have kicked both of them in the behind.”  At least someone paid attention.

Oscar De La Hoya:

While our first two Oscars suffer deflated legacy effects of being forgotten or overlooked, our third Oscar suffers the strange legacy effect of being too famous.  In his boxing prime, Oscar De La Hoya got so much attention and media coverage, and then got so much attention and media coverage for all his attention and media coverage, that his “Golden Boy” celebrity persona often outshone his boxing persona, and I think it has caused many to misjudge his career.

First, the accomplishments.  Over his career, which lasted from 1992-2012, including a gold medal in Barcelona, De La Hoya would win ten world titles spread across six different weight classes: junior lightweight, lightweight, junior welterweight, welterweight, junior middleweight, and middleweight.  His overall record was 39-6, including at least 30 wins by knockout, and many of his triumphs came against major stars of the day.  He crushed Rafael Ruelas in two rounds in 1995, when he was named The Ring’s “Fighter of the Year.”  He beat Julio Cesar Chavez for his second weight class belt in 1996.  He added his third by beating Pernell Whitaker in 1997, and mastered Hector Camacho in the same year.  In both 1997 and 1998, he was Ring Magazine’s best pound for pound fighter.  He lost to Felix Trinidad as a welterweight in 1999 in one of the biggest pay-TV events ever, and also one of the most controversial decisions ever (he dominated Trinidad for several rounds and then coasted, only to be upended by the judges).  He would lose a disputed split decision to “Sugar” Shane Mosley in 2000, and then again in 2003 in a hugely controversial affair (wherein De La Hoya landed cleaner blows and more than 100 more than Mosley).4  Between the two Mosley fights, De La Hoya notched a win against “Ferocious” Fernando Vargas, a longtime rival.  He became the first to collect his sixth weight class belt in 2004 by defeating Felix Sturm.  Overall, he defeated 17 world champions.  Late in his career, he fought Bernard Hopkins, Floyd Mayweather, and Manny Pacquiao well after he had lost the heat off his fastball, but through it all, he maintained his star power.


Indeed, De La Hoya is the most financially successful non-heavyweight ever, and is right up there with George Foreman.  He is without a doubt one of the biggest superstars of boxing from the post Ali era, and his boyish charm and charisma kept him squarely in the limelight for decades.  He generated nearly $700 million in Pay-per-view receipts.  He drew in waves of fans and provided a spark to the sport.  Being that famous can have an odd effect on a career.  I believe that his worldwide fame essentially created an image that was impossible to live up to, and which his (still amazing) boxing exploits failed to match.  Likewise, being such a famous face and squaring off against so many superstars late in his career left an image of repeated defeats in the minds of million tuned-in viewers.  Lesser celebrities would have neither the cultural undercurrent pushing them into those types of high-profile losses, nor the same number of eyes seeing them lose.  For a man so widely admired, his status as a boxer has been sold short.

A fair analysis of his career should place him in the top tier of pound-for-pound boxers, given his exploits across six weight classes and against several top names, including those couple massive bouts (Trinidad and Mosley II) which many believe he should have won.  He is probably not a Pantheon-level middleweight or welterweight, and perhaps not lightweight, but combine all three parts and you have a true legend.  All told, he was absolutely one of the most versatile fighters ever and one of the 30 or 40 greatest boxers of all time.  He should be remembered for that rather than his Pay-per-view stats and because his late losses happened in front of so many cameras.5


  1. A judge recently ruled that portions of Pistorius’s trial can be filmed by three remotely controlled cameras and broadcast live on South African television.  The ruling brought about applications to broadcast the trial by a TV news station, a cable provider that will launch a 24-hour channel focusing solely on the trial, and a radio news network.  The case has truly become the O.J. Simpson trial of South Africa.
  2. Gamble also had one of the best and most recognizable hairstyles in baseball, or perhaps sports, history.  He also finished his career with exactly 666 runs batted in.
  3. Win Shares is an attempt at an all-encompassing statistic that measures the estimated wins contributed by a player to his team for the season.  Robertson had a WS of 20.6 in the 82 game season of 1963-64.
  4. Mosley was later implicated in the BALCO performance-enhancing drugs scandal, and admitted to using PEDs during this fight.
  5. Although, unlike the two other Oscars above, it is hard to feel too bad for a man who is a hero to many and who is worth so many millions, simply because his boxing achievements are often overlooked.  His Golden Boy Promotions company has also been wildly successful since his retirement, becoming one of the sport’s leading promoters in just a few years.

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