WFM’S Chicago Sports Hall of Fame: The Chicago Cubs

Although a long suffering White Sox fan, I am not a Cubs hater. I root for them in a rather detached fashion. I don’t begrudge them success, although their sustained mediocrity over 65 years has rarely made that choice an issue. I like Wrigley Field. I do question the conventional wisdom that serious Cub fans massively outnumber White Sox fans. My experience is that if you poll lifetime Chicago natives, the fan split is rather equal. The Cubs advantage is that the vast majority of people who move to Chicago from other states almost always become Cub fans. Midwesterners were brought up watching the Cubs on WGN’s Superstation and almost all new arrivals choose to live on the north side. Wrigley is the greatest party in town. The downside of this profile is that large numbers of attendees at Cub games are clueless in terms of their understanding of baseball and its history. They are knowledge deficient and sorely in need of remedial training on the fundamentals. But, that’s OK. 

The Cubs and White Sox do have one thing in common- they are almost always mediocre. Each has won only one World Series in my 65 year sports viewing window. The Sox had a 88 year draught but the Cubs took losing to another level with 108 years between championships. WOW! I did celebrate the 2016 victory over the Indians only to lose my sense of joy and exhilaration when Donald Trump was elected President two weeks after the parade. OUCH!  The Cubs wore the banner of “Lovable Losers” proudly. They made the playoffs in 1984, 1989, 1998, 2003, 2007, 2008, 2015, 2016, 2017, 2018, 2020 and 2025. Their failures in the playoffs are legendary. A ground ball going thru Leon Durham’s legs in 1984 and Steve Bartman attempting to make the catch from the stands in 2003. The Cubs trade Lou Brock for Ernie Broglio in 1964 and let the greatest pitcher of the era, Greg Maddox, leave through free agency. Until Theo Epstein showed up, the Cubs had second rate GM’s and an awful player development history. The Wrigleys were cheap and invented the “College of Coaches” instead of choosing an actual manager. The 1969 collapse was epic- an 8 game lead on the Mets on August 15 dissolving in spectacular fashion. The Cubs actually ended the season 8 games behind the Mets- a 16 game reversal in 6 weeks. Sammy Sosa was electric until he wasn’t! The good news is they seem to be a stable and competent franchise now and good luck to them. Similar to the Bears and Sox, the Cubs have managed to produce some world class players even when the team history is poor. My Cubs Chicago Hall of Fame honorees are: 

1. Ernie Banks (1953-1971). “Mr Cub” is the starting point. His career is a study of athletic excellence and personal grace operating under a shadow of permanent disappointment. Banks never played in a single post season game. He remains the most beloved figure in franchise history and the absence of a championship ring doesn’t invalidate his legacy.  He won back to back MVP awards, made 14 All Star teams and retired as the franchise All time leader in homers and total bases. He was an excellent shortstop and then a smooth first baseman. He coined the slogan “Let’s Play Two” and was a role model for those who love everything about the game. 

2. Billy Williams (1959-1974). He had the sweetest swing of any left handed hitter in baseball history. He was nicknamed the “Iron Man” based on his 1,117 consecutive game playing streak. He was a 6 time NL All Star, hit 397 home runs and had a lifetime batting average of .290. He was the 1961 NL Rookie of the Year. He was elected to Cooperstown in 1987. He was not glamorous, was soft spoken but went about his business in an ultra professional manner. 

3. Ron Santo (1960-1973). This may be the most poignant name on this list. He played nine full seasons while managing diabetes in secret. This detail recasts his 342 home runs and 5 gold gloves as a much more impressive achievement than the numbers alone suggest.  Santo’s heel clicking celebrations after Cub victories are a sacred piece of Cub folklore and showed his over the top enthusiasm. His posthumous selection to the Hall of Fame corrected what had been a conspicuous oversight by Hall of Fame voters. He was a long time radio announcer and was hilarious, a pure homer and stylistically awful. He may have been my least favourite Chicago analyst, but I then remembered Irv Kupcinet on Bears radio broadcasts and I can at least acknowledge Santo’s passion. 

4. Fergie Jenkins (1966-1973, 1982-1983). A workhorse, an ace and a stud. He won the 1971 Cy Young Award and won 20 games six consecutive seasons. He won 284 games and was the first Cubs pitcher elected to the Hall of Fame. He churned out complete games at a record pace. He was reliable, well spoken and embodies a grand era of starting pitchers who basically refused to come out of any game. I miss those guys - screw pitch counts and 5 inning quality starts. Great job by Ferguson Arthur Jenkins- even his name was dignified. 

5. Bruce Sutter (1976-1980). He mastered the split finger fastball after an arm injury robbed him of his heater. He was one of the first shutdown closers. He won the 1979 Cy Young award on the strength of 37 saves and a 2.22 ERA. He was almost unhittable during his tenure with Cubs and management reacted by sending him to the Cardinals where he continued to excel and dominated a World Series.  Sutter was elected to the Hall of Fame in 2006.

6. Lee Smith (1980-1987). He took over the closing role from Bruce Sutter and turned it into a position of pure intimidation. Cubs historian Ed Hartig said there was nothing more menacing than watching Smith make his slow walk to the mound from the exposed Wrigley Field bullpen. He remains the franchise all time saves leader, made seven all star teams over an 18 year career and was elected to the Hall of Fame in 2019 by a unanimous vote of Today’s Game Era Committee. He had ten wonderful years after departing the Cubs, a familiar pattern for the north siders. 

7. Greg Maddox (1986-1992, 2004-2006). He is one of the outstanding pitchers of all time. And yes, he started with the Cubs. He arrived as a scrappy 20 year old who looked more like an accountant than a future ace. By 1992, he was the best pitcher in baseball following a 20-11 season and a Cy Young Award. Predictably, the Cubs decided to draw a line in the sand and Maddox departed after a bitter and nasty dispute with ownership. He then moved on to Atlanta and won three more Cy Young Awards and ended his career with 300 plus wins. He did return to Wrigley in 2004 and won his 300th game in a Cubs uniform, a fitting bookend to his 10 years with the club that originally signed him. The Cubs did retire his No 31- least they could do under the circumstances. 

8. Ryne Sandberg (1982-1994 1996-1997). Ryne was a second baseman who had all the tools; an expert fielder, a great baserunner and a batsman who could hit for power and average. A great clutch player as well. He played for 15 years, won the MVP in 1984 and was a nine time Gold Glove winner. He retired with 277 homers and a Hall of Fame plaque in Cooperstown. Sadly, he passed away last year. Along with Ernie Banks, the most popular Cub player in the modern era.  

9. Andre Dawson (1987-1992). He was an established star with Montreal when he joined the Cubs in 1987. He signed a blank contract just to escape Montreal’s artificial turf which was destroying his knees. He excelled for 6 years with the Cubs and won the NL MVP his first season in Chicago with a 49 homer-137 RBI campaign. The Cubs, being the Cubs, still finished last. The “Hawk” was inducted into the Hall of Fame in 2010 and his career numbers are breathtaking. He hit 409 homers and won nine Gold Gloves. He is one of only 8 players in history with more than 300 homers and 300 stolen bases. Another classy dude. 

HONORABLE MENTION 

1. Mark Grace (1988-2000). He led all of baseball in hits during the 1990’s decade and won 4 gold Gloves. He was a steady professional. He doesn’t have a Hall of Fame resume but was a genuine North Side institution for 13 years. 

2. Rick Reuschel (1972-1981, 1983-1984). He was a true star on some of the bleakest Cub teams in the 1970’s. “Big Daddy” made 3 All Star squads and finished second in the 1977 Cy Young vote after winning 20 games. The type of guy who never got his due because the organisation was so inept in building a decent roster. 

3. Ken Holtzman (1965-1971, 1978-1979). He threw 2 no hitters in a Cub uniform and remains the winningest Jewish pitcher in MLB history. He survived nine seasons across two Chicago stints, sandwiched around three World Series titles with Oakland. Another accomplished player the Cubs inexplicably let get away. 

4. Anthony Rizzo (2012-2021).  A marvelous first baseman who was the emotional leader of the Cubs core that finally ended the 108 year wait and the player who fittingly caught the final out of the 2016 World Series. He was selected to 3 All Star teams and won 4 Gold Gloves over ten seasons. He ended his career with the Yankees but his identity will always be one of the most beloved Cub players of his generation.

5. Sammy Sosa (1992-2004). Based on the numbers, Sammy definitely qualifies for the Hall of Fame. Unfortunately, the steroid allegations hang over his head and I, like MLB Hall of Fame voters, choose to view his career with a jaundiced eye. The man hit 60 plus homers three different times and the 1998 season was one of the most electric in history. I remember Sosa jerseys going for 1000 dollars a pop at charity auctions. Sammy had style, power and people paid to see him. Cheating doesn’t age well though!