Want the Morning Rundown? One email a day gets you all the sports headlines you need.

* indicates required
Close
top-25-chicago-sports-legends-chicagoside

The 25 Greatest Chicago Sports Legends. Period.

almanac-significance-smallEDITOR’S NOTE: This story is an important part of something bigger, something special, known as “The ChicagoSide Sports Almanac of Significance, Vol. 1,” which offers you, dear reader, a content series as-yet unavailable on the Web: A unchallengeable compendium of iron-clad analyses of Chicago sports topics of consequence, e.g. Top 25 Chicago Sports Legends, Best Chicago Team Ever, Best Facial Hair. >> For a full index of all 15 stories, click here.


When we set out to anoint the greatest sports legends in Chicago’s long and storied athletic history, we were assured of two things: We would get it absolutely correct, and no one would have any arguments with our choices.

If only reality were such an elegant thing. Instead, we argued internally for weeks, then we nibbled at the list for days before chiseling the ultimate list of legends in Internet stone. It’s important to note that this isn’t a list of the 25 greatest athletes ever to toss on a Chicago uniform. What we decided to do was use criteria that could easily be quantified, such as impact, “Chicagoness,” transcendence, charisma (and things like stats and championships, as well). If your favorite legend isn’t on the list, you can take some comfort in knowing he or she probably was at one point, and one of us here in the office is almost certainly still holding a grudge over his or her exclusion.

But a list like this is built to be exclusive. Everyone here is an icon whose influence has either changed their game or beyond. We look forward to your total agreement!

25. Arch Ward

ArchWard
Remember how much fun the Ravens-49ers Super Bowl was? Or how about arguing over who should be in the All-Star Game?  And if you’re into boxing, checking out a Golden Gloves tournament. Well, you have Arch Ward to thank for all of that. Ward was the sports editor of the Chicago Tribune and used that position to create events, and even leagues. In 1933 with Chicago hosting the Century of Progress World’s Fair, he came up with the idea to stage a game between the best players in the National and American leagues. The idea stuck, and now it’s the Midsummer Classic.

Ward also created the All-America Football Conference. The league only lasted four years but gave us the 49ers and Browns (now Ravens), two franchises with great imprints on football. Combine that with what the Golden Gloves has become, and you have an unsung, but influential, legend.

24. Ozzie Guillen

OzzieGuillen
If not for his World Series win with the White Sox in 2005 (the first World Series title the Sox have enjoyed since 1917), then for his distinct personality, Ozzie makes the list. He kept it real during his time as manager of the Sox, amassing more than 600 wins during his tenure and becoming the first Latino manager in Major League history to win a World Series. And he did it while puppeteering the media in whatever brash manner he pleased. Reporters loved to bait him for a quick soundbite, but Ozzie became the ringmaster of the media circus; his comments were calculated and purposeful, even if he misfired on occasion. Ozzie’s way with words arguably made him the face of Chicago sports for a while. He brought respectability back to the South Side and proved that Chicago is, and always will be, a baseball town.

23. Ray Meyer

RayMeyer
DePaul basketball once really mattered. The Bulls were a secondary hobby and the Illini weren’t the top college team in town. That was because of Ray Meyer, the DePaul head coach from 1942-1984. In that time, Meyer coached greats such as George Mikan and Mark Aguirre. He won 724 games and led the Blue Demons to the 1945 NIT title, along with the 1979 Final Four.

It was around the time of the Final Four team that the Blue Demons really popped. They moved to the Rosemont Horizon and were seemingly on national TV every week. Meyer was of course the catalyst, with his kindly persona winning over fans across the country. What’s happened to DePaul since he retired in 1984 is a testament to what Ray Meyer meant to the program. And to basketball as a whole.

22. Kelly Amonte Hiller

KellyAmonteHiller
If Phil Jackson is revered in this town for winning six championships, shouldn’t we have an artist working on an Amonte Hiller statue pronto? The Northwestern University women’s lacrosse coach has seven NCAA championships under her belt, along with seven Coach of the Year awards, and is already in two halls of fame (Lacrosse and Italian-American), and yet it feels like she’s just getting started. NU hadn’t even had a varsity women’s lax team in 10 years until Amonte Hiller showed up, resurrected it, and then piloted it to an undefeated season and its first national championship in 2005. The team has gone on to win seven trophies in nine years, and under Amonte Hiller’s stewardship, Northwestern has produced 45 All-Americans, and taken down 11 player-of-the-year awards (by position). Forget the championships, if the mark of a great coach is making her players the best they can be, Amonte Hiller is clearly one of the all-time greats.

21. Stan Mikita

StanMikita
The Blackhawks’ first golden age was defined by two men: Bobby Hull and Stan Mikita. While Hull was the flashy superstar with the Hollywood looks, Mikita was the glue of the 1960s teams. Mikita was initally a hothead, but he eventually cooled down, winning two Lady Byngs for being the league’s most gentlemanly player. And though he mellowed out, his play never wavered. Though Hull was the one that got most of the attention, Mikita led the NHL in scoring four times while consistently winning face-offs and playing strong two-way hockey. Mikita and Hull also pioneered the use of the curved stick, making an impact well beyond just the 1960s Hawks.

But unlike Hull, Mikita spent his entire career with the Hawks and hasn’t tarnished his legacy with his off-ice behavior. Mikita is a true ambassador of what the Blackhawks want to be, and what they should be.

20. Sid Luckman

SidLuckman
When the Bears were thrilling the nation with their T formation, their quarterback was Sid Luckman. And when they were a dynasty in the 1940s Luckman was their quarterback, leading them to four championships. Out of Columbia University, Luckman was George Halas’ choice to run his offense. And the choice, like a lot of what Halas did, was brilliant. Luckman threw for a Bears record 14,686 yards. Never mind that the Bears haven’t had anybody challenge that since, that total was an impressive mark for that era. He also had seven touchdown passes in one game, and was a five-time all-pro.

By today’s standards, Luckman’s numbers wouldn’t be great. But all he did was help turn pro football from a grinding running game into the aerial sport we watch today. Now, if only the 2013 Bears could find somebody as good as him.

19. Ryne Sandberg

RyneSandberg
The former Cubs second baseman is second to none. He made 10 consecutive All-Star games, won nine consecutive Gold Gloves and still holds the Major League record for overall fielding percentage (.989) at the position.

It’s hard to argue with a résumé like that. Yet Ryno is perhaps best remembered for what he didn’t do. He retired  prematurely during the 1994 season, claiming that he lacked a good mental approach to the game. From his perspective, why should the Cubs organization pay his salary if he wasn’t meeting Major League standards? It’s a borderline miracle that Sandberg, who returned in 1996, copped to a subpar performance and bowed out because of it, especially in the clandestine age of baseball that we live in today. Though Sandberg never won a World Series with the Cubs, he played the game with uncompromising integrity. That’s more than you can say for some so-called “champions” these days.

18. Jerry Reinsdorf

Reinsdorf
Seven championships, two new stadiums, too many philanthropic contributions to count. Yet Jerry Reinsdorf isn’t beloved in Chicago like owners Bill Veeck or Rocky Wirtz.

Reinsdorf is equal parts hated and admired in Chicago. And there are certainly reasons for that. He let old Comiskey Park bleed and threatened to move to St. Petersburg, Florida before getting a new park built, one that was outdated the second it opened. He was a hawk during the 1994 MLB players strike, a stoppage that killed a great White Sox chance to win a World Series. He also let Jerry Krause dismantle the dynasty Bulls, and hasn’t allowed the current team to go over the luxury tax to get players needed to beat the Miami Heat.

But seven titles. In Chicago. Seven titles. Just ask Cubs fans how they’d feel about one, or how fondly Sox fans recall 2005. That’s Reinsdorf’s legacy.

17. Harry Caray

HarryCaray
Harry Caray never won a game for the Cubs or the White Sox. He never drove in a run or struck anybody out. All he did was sell the product better than any announcer ever could.

Caray started his career in St. Louis in 1945, spent 1970 with Oakland and then came to the White Sox for the 1971 season. It was during his tenure with the White Sox when Caray began singing the seventh-inning stretch at home games. That, his outspoken nature, and partnership with Jimmy Piersall, made him a beloved announcer by White Sox fans. In 1982, Caray jumped to the Cubs. Now calling games on the WGN superstation, Caray helped the Cubs become the national brand they are today. In the process, he helped himself become a national brand and favorite pitchman for Budweiser.

Caray’s legacy will always be his love of baseball and calling games. Holy Cow, indeed.

16. Luis Aparicio

LuisAparicio
Aparicio was a force to be reckoned with in the middle of the White Sox infield, proving himself from the get-go by winning the Rookie of the Year award in 1956. Let’s take a quick look at Little Louie’s big career: 10 All-Star games, nine stolen-base titles and nine Gold Gloves. While shortstop has turned into a power position in the modern era, Aparicio was once the gold standard for slick-fielding, speedy shortstops. When he retired, he held the record for most games played at shortstop, as well as most double plays and assists. Simply put: no player defined the “Go-Go” era of White Sox baseball like Aparicio.

15. Phil Jackson

PhilJackson
No one regarded as a “zen master” has as much bling as Phil Jackson. All Jackson ever did as a coach of the Bulls was take home six rings, and revolutionize the game with the triangle offense. It’s tough to believe that on a team with Michael Jordan, we’d still be talking this much about the coach, but such is the size of Jackson’s intellect, character and, yes, ego, that he warrants placement on this list. Hard to imagine Erik Spoelstra is going to be lionized when his career is over.

The only thing keeping Jackson down on this list is the latter-day waning of his Chicagoness. He headed west to the Lakers, won five more championships, got in deep with the Buss family and is now just as closely associated with purple, yellow and Kobe Bean than the red and black.

14. Bobby Hull

BobbyHull
Robert Marvin Hull is a flawed hero, a semi-tragic but incredibly gifted athlete. If ever there’s an athlete you don’t want to know anything about beyond his performance, it’s the Golden Jet.

Before Patrick Kane was taking Hawks’ fans breath away there was Hull. He had the rocket slap shot, and the bright locks that blew gracefully in the breeze as he skated down the ice. He was a key member of the 1961 Stanley Cup champion Hawks and won two league MVPs.

But, unfortunately, there’s much more to Hull’s legacy than hockey.

His daughter, so scarred by seeing Hull allegedly beat her mother, became a lawyer specializing in domestic abuse. He was also quoted in the Russian media saying “Hitler, for example, had some good ideas. He just went a little bit too far.”

As a hockey player, Hull’s legacy is one of brilliance. There’s just more to him than hockey.

13. Scottie Pippen

ScottiePippen
Never has a second fiddle been played so deftly as when Scottie was on the same Bulls teams as Michael Jordan. It’s been said before, but it’s worth repeating: Playing on any other team at his peak, Scottie Pippen would have been elevated to superstardom. Funny how Chris bleepin’ Bosh gets to be part of a “Big Three” for playing with LeBron, but Pippen comprised one-half of the deadliest duo the sport has ever seen and he’s remembered as the guy beside Michael.

Well, not everyone feels that way. When the NBA put together a list of the 50 greatest players of all-time to mark the league’s 50th anniversary, there was Pippen’s name on the list. He’s a living legend who, unlike Michael, has stuck around Chicago and the Bulls. One of the all-time great small forwards, in 17 seasons, Pippen’s teams made the postseason 16 times.

12. Gale Sayers

GaleSayers
Gale Sayers only played in 68 games. He only gained 4,956 yards and never appeared in one playoff game. Yet he’s one of Chicago’s most beloved athletes.

Why? Just check out any highlight reel.

He ran with a grace that hadn’t been seen before and has only been approached since by Barry Sanders. Even on some mediocre Bears teams, Sayers was a threat to score every time he touched the ball. His moves will live on in football history, and when a 1968 knee injury robbed him of his pizzazz, he still returned in 1969 to win a rushing title despite never gaining more than 28 yards.

Sayers also befriended Brian Piccolo, and stood by his friend until Piccolo’s death. When he was inducted into the Pro Football Hall of Fame, George Halas put it best about Sayers: “His like will never be seen again.”

11. Bill Veeck

BillVeeck
Veeck as in wreck, and the man lived up to the rhyme with the infamous (but also pretty awesome) Disco Demolition at Comiskey Park. The night may have turned into a riot (and a forfeit), but as baseball promotions go, how many bobblehead days have become cultural touchstones? Pro sports worsen the more buttoned-up they become, and Veeck was basically an anarchist in a country club.

Cubs fans may cringe at seeing Veeck this high up the list, but it’s important to remember that when his dad was Cubs president, 13-year-old Bill was the young genius who came up with the idea of planting ivy along Wrigley’s brick wall, maybe the singular master stroke that makes Wrigley a landmark, and not the site of another type of demolition.

10. Ron Santo

RonSanto
Ernie Banks may have earned the title of Mr. Cub, but can anyone name someone who put their heart at the mercy of the Cubs the way Santo did. Sure, his broadcast career divided fans, as his homerism took on cartoonish proportions, but he and partner Pat Hughes had a chemistry that made “Pat and Ron” as deeply Chicago as Jewel/Osco.

And let’s not forget Santo’s playing career. You know he had great power at the hot corner in his era, but what’s often overlooked is how Santo was a count worker before working a count was cool. He twice led the league in OBP, a stat that if he played in the Moneyball era, would have sabermetricians drooling.

A heel-clicking, Cubbie-blue-bleeding original, Santo was a tremendous player, and a North Side icon.

9. Frank Chance

FrankChance
Here’s a little little-known trivia you can use to stump your seamhead friends at the next game: The Cubs have actually won two World Series. It’s true! It does feel as though it would go against nature’s laws if it happened again, but at one sepia-toned time in history the Cubs not only won a World Series, they were sort of a dynasty. From 1906 to 1910 they played in four of five World Series, winning in 1907 and 1908. And who was the player-manager who led the Cubs through all four of those series? Our man Chance.

For that reason alone, the speedy Chance (who once stole 67 bases in 125 games) makes it into our Top 10. That, and he was the business end of maybe the most famous double-play combo in history: TInker to Evers to Chance. Cool footnote: The Peerless Leader was the first player ever ejected from a World Series game for arguing with an ump.

8. Joe Jackson

JoeJackson
Much of ‘Shoeless’ Joe Jackson’s legacy is centered on  what he could have been if  Kenesaw Mountain Landis hadn’t banished him from baseball before the 1921 season.

Jackson, as we all know, was one of eight Black Sox kicked out of baseball for their involvement in a plot to throw the World Series. Never mind that Jackson might have been too ignorant to know what he was doing, or that he hit .375 in the Series, Jackson’s career was cut short.

But oh what a career that was. Jackson was a career .356 hitter, the third highest in baseball history. He only played five seasons for the White Sox—including just 17 games in 1918—but hit .340 with a ridiculous 159 OPS-plus. He was also part of the White Sox’s 1917 World Series champion, the last until 2005.

That’s all impressive, but he could have been so much more. The ‘what-ifs’ are painful, but also form part of his allure.

7. Red Grange

RedGrange
Red Grange was Chicago’s first modern superstar. He wasn’t before Joe Jackson or Frank Chance, but he was the first celebrity athlete the city’s seen. Grange graduated from Wheaton High School and went onto the University of lllinois, where he became a national celebrity. Grantland Rice waxed purple poetic about Grange, and Warren Brown named him the “Galloping Ghost.”

Needing a boost for his fledgling team, George Halas signed Grange and took him on a 19-game barnstorming tour that built pro football’s place in America. Grange and Halas had a falling out, forcing the Ghost to create his own league and team in 1926, the New York Yankees. Grange returned to the Bears in 1929 after missing 1928 with injury, and starred in Chicago until 1934. His legacy isn’t just as a player but as a drawing card and star, a star that gave pro football the boost it badly needed.

6. Dick Butkus

DickButkus
Dick Butkus is the personification of Chicago football. He graduated from Chicago Vocational High School and went on to the University of Illinois. He was an All-American there, led the Illini to a win in the 1964 Rose Bowl, and finished third in the 1964 Heisman Trophy balloting. After that, it was clear Butkus was born to play middle linebacker for the Bears. Following in the footsteps of Bill George, Butkus made an immediate impact in the NFL. He was the toughest, meanest, most intimidating force the game had seen, and his highlight reels to this day are awe-inspiring.

Not only did he play for quintessential Chicago teams, but he has a quintessential Chicago look and sound. He wears a Chicago mustache and has an accent that is as Chicago as anything. Butkus only played nine seasons and never appeared in one postseason, but he’s the greatest middle linebacker in Chicago Bears history, a title that means as much as any ring could.

5. Ernie Banks

ErnieBanks
No, Ernie Banks’ Cubs didn’t win anything. The closest they came was the fateful 1969 season, when they won 92 games but slowed down late and were passed by the Mets.

Somehow, that doesn’t tarnish Mr. Cub’s legacy. Lack of team success aside, Banks was a great player. He won two MVPs (1958, 1959) and hit 512 career home runs. He was one of the first power-hitting shortstops in baseball, eventually transitioning to first base and continuing to hit for power. Banks was also the Cubs’ first black star, something that never should be forgotten when his legacy is discussed.

Banks also had that magical personality. He always wanted to play two, and to this day is the embodiment of everything good about the Cubs. Along with Billy, Fergie and Ronnie, Banks was a beloved member of the Cubs’ most beloved era.

4. Mike Ditka

MikeDitka
A hurricane vs. Pete Carroll? How about a Harbaugh? Let’s face it, no one could stand up to elemental forces quite like Ditka, and da coach who brought the last Super Bowl to town still has more cachet in this town than any skipper who’s followed, and more style than any of the empty jumpsuits in the NFL today.

He’s the only Bear to have played a part in the team’s last two championships: In 1963 as a player and 1985 as the coach. And over his 11 years as coach of the Bears, the team won its division six times. And let’s not forget that the conservative Ditka decided not to run for U.S. Senate in 2004. Had he, Hurricane Ditka may have swept Barack Obama out of the election, and at the very least delayed the President’s tenure.

3. Walter Payton

WalterPayton
Clear the next 20 minutes of your life. Go to YouTube. Type Walter Payton’s name and just click on the first highlight reel that comes up. We’ll be waiting for you when you come out of the trance.

The fact is that no matter how much we revere our memories of Sweetness, and how clearly we can recall his epic runs—juking and flattening every defender—he was better than we remember. They say our memories exaggerate, but they’re actually modest when remembering Payton’s runs. The numbers, though, remember him well: For a spell he held the record for career rushing yards, touchdowns, carries and yards, and he still holds the record for most TD passes for a non-quarterback. While the Punky QB, the Fridge and the Stache may have stolen the limelight, no one has ever run the ball with as much grace and tenacity as Payton, and we have the video to prove it.

2. George Halas

GeorgeHalas
If all George Stanley Halas did in his 88 years of life was play right field for the New York Yankees and earn a Bronze Star in the navy during World War II, it would have been an extremely impressive life.

Halas, of course, was more than that.

He took control of the Decatur Staleys in 1921 and moved the team to Chicago, eventually renaming them the Bears and building them into the city’s most popular and important team. He owned them until his death in 1983 and coached them to 318 wins and six NFL championships. Everything the Bears are now is because of him: their colors are the same as the University of Illinois, his alma mater. Their greatest eras were with him in charge, and he hired the man who coached them to their only Super Bowl title.

Papa Bear’s initials are worn on the team’s left arm, but in reality, the team is a memorial to Halas.

1. Michael Jordan

MichaelJordan
No matter what latter-day Phil Jackson says, Air Jordan was simply the greatest player to ever play the game. No athlete has ever had their signature moves mimicked ubiquitously, and in no other sport is every star prospect held up as possibly the Next _______. But that’s just what Jordan meant to NBA and the game of basketball. What makes Jordan the ultimate Chicago sports legend is the way he became synonymous with Chicago for nearly a decade. Bringing home six rings is nothing to sneeze at, but Jordan had kids in Jacksonville and Bangor rocking jerseys with CHICAGO printed across the front.

Outside of sport, there’s never been a more dominant star. Jordan took endorsements to another level, essentially elevating Nike every time he rose off the court, and trading credibility points with Spike Lee. And let’s not forget that in the ‘90s, aided by the rise of hip-hop, the NBA stood at our culture’s centerstage. And there was His Airness, leaping over it all, tongue hanging out.

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>