Last Updated: June 17th, 2026 by Matthew Brown
Last Updated: May 26th, 2026 by Michael Schatz
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The ivy-covered walls of Wrigley Field have witnessed more than their share of baseball greatness. While Ernie Banks, Billy Williams, and Ron Santo found their way to Cooperstown, countless Cubs legends who defined afternoons on the North Side still await recognition.
From the post-war era through the steroid age and beyond, these twenty Chicago icons left indelible marks on franchise history. Their contributions shaped Cubs baseball for generations of fans who packed the bleachers and sang along to the seventh-inning stretch.
The franchise legends who defined generations at Wrigley Field but never received the call from Cooperstown.
We are counting down from #20 to #1, so the argument builds as the list gets closer to the top spot.
#20 Jody Davis: The Folk Hero Behind the Plate
Jo-dee! Jo-dee! The chant still echoes in the memories of 1980s Cubs fans who packed Wrigley Field. Davis’s clutch hitting and handling of the pitching staff during the 1984 and 1989 playoff runs made him a North Side favorite.
That iconic fan chant and his leadership behind the plate defined an era of Cubs baseball. His ability to call a game and his surprising power at the plate made him one of the National League’s best catchers of the decade.
Davis’s 122 home runs over eight seasons as a Cub and his two All-Star selections showed he was more than just a fan favorite. His connection with Cubs fans and his role in the franchise’s most memorable moments of the 1980s secured his legacy.
#19 Dave Kingman: Kong’s Mammoth Blasts onto Waveland
Before Sammy Sosa, there was Kong. Dave Kingman’s towering home runs onto Waveland Avenue became the stuff of North Side legend, with his 48-homer season in 1979 standing as a Cubs record for nearly two decades.
That massive swing and all-or-nothing approach made every at-bat must-see entertainment for Cubs fans. His tape-measure shots created memories that lasted far longer than his batting average suggested they should.
Kingman’s 94 home runs over three seasons on the North Side showed pure power in its rawest form. His ability to hit balls farther than anyone had ever seen at Wrigley made him an unforgettable part of Cubs history.
#18 Bill Buckner: Before That One Play in Boston
Before that fateful moment with the Red Sox, Billy Buck was one of the Cubs’ most consistent hitters. His National League-leading .324 batting average in 1980 and legendary battles with injuries showed Chicago fans what true grit looked like.
That unique crouched stance and incredible contact skills made him the perfect table-setter for those early 1980s Cubs teams. His ability to hit for average despite chronic ankle problems demonstrated remarkable determination.
Buckner’s .300 average over seven seasons as a Cub and his Gold Glove defense at first base made him one of the franchise’s best players of that era. His Cubs career deserves to be remembered separately from that October night in Shea Stadium.
#17 Shawon Dunston: The Cannon-Armed Kid from Brooklyn
The Shawon-O-Meter in the bleachers tracked his batting average, but it was Dunston’s rocket arm that made him unforgettable. His throws across the diamond regularly hit 90 mph, making routine grounders into must-watch events at Wrigley.
That endless energy and million-dollar smile made him a fan favorite during both his Cubs stints. His raw athleticism and aggressive style embodied the spirit of Cubs baseball in the 1980s and 1990s.
Dunston’s .269 average over 12 seasons on the North Side and his All-Star selections showed he was more than just an arm. His passion for the game and connection with Cubs fans made him one of the most beloved players of his generation.
#16 Randy Hundley: The Catcher Who Revolutionized the Position
Randy Hundley revolutionized catching with his one-handed style behind the plate. His innovative technique of catching with one hand while keeping the other protected changed how catchers played the position across baseball.
That Gold Glove in 1967 and his handling of the Cubs’ pitching staff made him a North Side institution. His durability behind the plate, catching over 150 games in multiple seasons, set new standards for the position.
Hundley’s leadership and defensive excellence anchored those competitive Cubs teams of the late 1960s. His .236 average as a Cub understates his value to a franchise that found stability behind the plate for the first time in years.
#15 Alfonso Soriano: The Hop That Electrified Wrigley
That signature hop before every catch became as much a part of Wrigley Field as the ivy itself. Soriano’s power and speed combination made him one of the most exciting players to wear Cubbie blue in the 2000s.
His 181 home runs over six seasons on the North Side showed why the Cubs made him their first nine-figure free agent. That ability to hit for power from the leadoff spot made him a unique weapon in the Cubs lineup.
Soriano’s 30-30 season in 2007 and his consistent production gave Cubs fans hope during the playoff runs of that era. His infectious energy and game-changing ability made every at-bat an event.
#14 Andy Pafko: Handy Andy of the Post-War Era
Before the Cubs’ dark days of the 1950s, Andy Pafko was their five-tool star. His contributions to the 1945 pennant-winning team helped lead Chicago to the World Series, an appearance they wouldn’t repeat for 71 years.
His .304 average with 36 homers in 1950 showed just how complete a player Handy Andy was during baseball’s post-war golden age. His ability to play multiple outfield positions with excellence made him invaluable.
Pafko’s .296 average over seven seasons as a Cub and his consistent production made him one of the franchise’s best players of the 1940s. His trade to Brooklyn remains one of the most controversial moves in Cubs history.
#13 Hank Sauer: The Mayor of Wrigley Field
Before Ernie Banks owned the bleacher crowd, Hank Sauer was Chicago’s beloved slugger. His MVP season in 1952, with 37 homers and 121 RBIs, made him the first Cub to win the award in seven years.
Those massive home runs and friendly connection with the bleacher bums earned him his famous mayoral nickname. His left-handed power stroke was perfectly suited to Wrigley’s dimensions and afternoon winds.
Sauer’s 198 home runs over seven seasons on the North Side made him the franchise’s premier power hitter of the early 1950s. His popularity with fans and consistent production defined Cubs baseball in the post-war era.
#12 Rick Monday: The Man Who Saved the American Flag
While his 1976 flag-saving heroics came as a Dodger, Rick Monday’s entire Chicago career deserves celebration. His steady center field play and clutch hitting made him a Wrigley Field favorite throughout the early 1970s.
That smooth left-handed swing produced 106 homers in a Cubs uniform and solid defense in center field. His ability to hit for power and get on base made him a valuable piece of those competitive Cubs teams.
Monday’s five seasons on the North Side showed Cubs fans a complete outfielder who could do everything well. His .270 average and professional approach set the standard for Cubs center fielders of that era.
#11 Bill Madlock: The Mad Dog’s Batting Titles
Though his best years came after leaving Chicago, Mad Dog Madlock showed Cubs fans what they would be missing. His back-to-back batting titles in 1975 and 1976 made him the first Cub to win consecutive National League batting crowns.
That .336 average in a Cubs uniform over three seasons only hints at the hitting machine he would become. His pure hitting ability and fiery temperament made him one of the most exciting young players in franchise history.
Madlock’s trade to San Francisco remains one of the most regrettable moves in Cubs history. His four career batting titles suggest what might have been if Chicago had held onto their young star.
#10 Don Kessinger: The Shortstop Who Defined an Era
For 12 seasons, Don Kessinger’s acrobatic plays at shortstop thrilled Cubs fans during the franchise’s most frustrating era. His six All-Star selections and two Gold Gloves came during a time when shortstops were known for their gloves, not their bats.
Those double plays with Glenn Beckert became baseball ballet at Wrigley Field throughout the late 1960s and early 1970s. His range and sure hands anchored Cubs defenses that featured some of the best infields in baseball.
Kessinger’s .252 average as a Cub tells only part of the story of his value to those teams. His leadership and defensive excellence made him the prototype for the modern defensive shortstop.
#9 Rick Sutcliffe: The Red Baron of the 1984 Dream
The Red Baron’s magical 16-1 run after joining the Cubs in 1984 remains one of baseball’s greatest mid-season acquisitions. His Cy Young performance nearly carried Chicago to their first World Series since 1945.
That red beard and fierce competitiveness made him the perfect pitcher for the Wrigley faithful during that unforgettable summer. His dominance down the stretch gave Cubs fans their first taste of October baseball in nearly four decades.
Sutcliffe’s 82 wins over eight seasons on the North Side and his leadership in the clubhouse made him a franchise icon. His connection to the 1984 team ensures his place in Cubs lore forever.
#8 Derrek Lee: The Smooth First Baseman of 2005
In 2005, Derrek Lee put together one of the greatest seasons ever by a Cubs first baseman. His league-leading .335 average, 46 homers, and Gold Glove defense highlighted a spectacular campaign that saw him lead the league in multiple offensive categories.
That smooth swing and vacuum cleaner glove made him the perfect successor to Mark Grace’s legacy at first base. His combination of power, average, and defense represented the complete package at the position.
Lee’s consistency over six seasons on the North Side gave Cubs fans hope during the wilderness years before the championship. His 179 home runs as a Cub and his graceful style made him one of the most respected players of his generation.
#7 Carlos Zambrano: The Last Angry Pitcher at Wrigley
Big Z’s emotional outbursts sometimes overshadowed his remarkable talent on the mound. His no-hitter and three Silver Slugger awards showed his unique combination of pitching prowess and hitting ability that made him a throwback to earlier eras.
That fierce competitiveness and .238 career batting average made him the last of baseball’s true dual threats. His 125 wins as a Cub came with the kind of passion that either thrilled or terrified Cubs fans.
Zambrano’s intensity defined an era of Cubs baseball that fell just short of championship glory. His ability to dominate games both on the mound and at the plate made him one of the most entertaining players in franchise history.
#6 Aramis Ramirez: The Clutch Corner Who Fixed Third Base
After decades of searching for Ron Santo’s heir, the Cubs finally found their answer in Aramis Ramirez. His walk-off heroics and consistent power made him the cornerstone of those contending Cubs teams throughout the 2000s.
That smooth swing from the right side produced 239 homers in Cubbie blue and a .294 average that made him one of the era’s most productive third basemen. His ability to drive in runs in crucial situations became his calling card.
Ramirez’s quiet leadership and professional approach made fans forget about the third base curse that haunted Wrigley for decades. His nine seasons on the North Side represented stability at a position that had known only chaos.
#5 Stan Hack: The Greatest Cubs Third Baseman Before Santo
Before Ron Santo owned the hot corner at Wrigley, Stan Hack was Chicago’s model of consistency through the 1930s and 1940s. His .301 lifetime average and five All-Star selections only hint at his importance to those Cubs teams.
That sweet left-handed stroke and stellar defense made him the prototype for every Cubs third baseman who followed. His ability to get on base and score runs made him the perfect leadoff man for championship-caliber teams.
Hack’s four World Series appearances with the Cubs and his leadership during baseball’s golden age deserve greater recognition. His 1,092 runs scored as a Cub remained a franchise record for third basemen for decades.
#4 Kerry Wood: Twenty Strikeouts and What Could Have Been
On May 6, 1998, Kerry Wood painted the single most dominant pitching performance in baseball history. His 20-strikeout masterpiece against the Astros showed what might have been if injuries hadn’t robbed him of his prime years.
That wicked slurve and blazing fastball made him Chicago’s pitching idol for a generation. His Rookie of the Year campaign promised a Hall of Fame career that injuries would cruelly derail.
Wood’s transformation into a dominant closer late in his career and his emotional final game at Wrigley showed the deep connection between player and city. His 1,582 strikeouts in a Cubs uniform tell the story of brilliance interrupted.
#3 Rick Reuschel: Big Daddy’s Underrated Brilliance
They called him Big Daddy, and Rick Reuschel’s contributions to Cubs history have been unfairly overlooked for decades. His 135 wins and solid ERA in a Cubs uniform came during some of the franchise’s leanest years on the North Side.
Modern analytics suggest he was one of the most valuable pitchers of his era, combining durability with surprising athleticism despite his frame. His ability to field his position and help himself at the plate made him a complete pitcher.
Reuschel’s consistency through the 1970s gave Cubs fans something to cheer about during otherwise forgettable seasons. His two All-Star selections as a Cub only hint at the quality of his work on the mound.
#2 Mark Grace: The Pure Contact Hitter at Wrigley
Nobody collected more hits in the 1990s than Mark Grace. His sweet left-handed stroke and Gold Glove defense made him the perfect Cubs first baseman for a generation of fans who grew up watching him patrol the right side.
His .308 average as a Cub and league-leading hit totals throughout the decade remind us of a time before launch angles dominated baseball. That smooth swing produced line drives to all fields with remarkable consistency.
Grace’s postseason heroics in 1989 and his leadership in the clubhouse made him the face of Cubs baseball during an era of near-misses. His 2,201 hits in Cubbie blue represent the standard for contact hitting at Wrigley Field.
#1 Sammy Sosa: The Slugger Who Changed Everything
Love him or doubt him, Sammy Sosa transformed Cubs baseball forever. That magical summer of 1998, with the home run chase and chest-thumping celebrations, brought baseball back from the brink and made Wrigley Field the center of the sports universe.
His 545 home runs as a Cub and that infectious hop made afternoon baseball at Clark and Addison must-see television across America. Three consecutive seasons of 60-plus homers created a phenomenon that transcended the game itself.
The steroid cloud has kept him from Cooperstown, but no player in franchise history brought more electricity to the ballpark. His impact on Cubs culture and Chicago’s North Side remains immeasurable two decades after his final curtain call.
Final Thoughts
These twenty Cubs legends represent generations of excellence on the North Side, from the post-war glory days through the steroid era and beyond. Their contributions to franchise history transcend statistics, embodying the spirit of afternoon baseball at Clark and Addison.
While Cooperstown may never call their names, these players remain immortal in the hearts of Cubs fans who witnessed their greatness. The ivy-covered walls remember every home run, every diving catch, and every moment that made Wrigley Field the most beloved ballpark in baseball.