The Best Wrestlers From Chicago In Wrestling History

Hamish Woodward

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Chicago is a huge area for professional wrestling, having some of the most passionate and excited wrestling fans across the world.

WWE and AEW have made the city a hub for their biggest shows, bringing some of the best wrestling events ever seen to the city in Illinois.

In this article, we’ll take you through all the best wrestlers to come from Chicago, analyzing why they deserve to be named the stop stars to come from the Second City.

CM Punk making his hometown entrance in Chicago at Money in the Bank 2011.

One name you will not see on this list is Hawk and Animal, also known as The Road Warriors.

While they worked in and became synonymous with Chicago, the pair actually hailed from Minnesota and Florida, respectively.

Due to this, we will not be including the iconic duo in this list, but not for their lack of legendary status in professional wrestling.

7. Adam Pearce

While he now works as the on-screen authority figure in the WWE, Adam Pearce was actually an accomplished wrestler during his day.

He traded the NWA World’s Heavyweight Championship back-and-forth with Colt Cabana in the 2010s, establishing himself as a world champion on the indies.

In a two-decade wrestling career, he became a huge name on the independent wrestling scene and is still considered one of Chicago’s favorite superstars to this day.

He was hired as a trainer by the WWE in 2014, helping to bring through the next generation of superstars.

6. Colt Cabana

colt cabana contract

One of the most influential wrestlers in modern times hails from Chicago, and that is Colt Cabana.

The AEW wrestler revolutionized pro wrestling podcasts with his “Art of Wrestling” podcast, as well as with merchandise sales thanks to collaboration with ProWrestlingTees.com.

While he only had a short run in the WWE as “Scotty Goldman”, Colt Cabana is a legend of the indie wrestling scene, spending the last two decades making his living in wrestling.

As a former NWA World Heavyweight Champion, he joined the lineage of champions that include Ric Flair and Dusty Rhodes, cementing Colt Cabana as one of the best wrestlers to come from Chicago.

5. Juice Robinson

AEW’s Juice Robinson is still in the midst of his career, but has quickly established himself as one of Chicago’s best ever wrestlers.

Since his release from WWE (where he wrestled in NXT as “CJ Parker”), Juice Robinson moved to NJPW and made a new name for himself.

He won tag team gold with David Finlay as “FinJuice”, before joining Bullet Club alongside the likes of Jay White and KENTA (two of the best Kiwi and Japanese wrestlers ever, respectively).

In 2022, he signed for AEW and became one of their hottest signings. A year later, he joined up with Jay White to form Bullet Club Gold, propelling him into the main event with a five-star match against FTR on Collision.

4. One Man Gang

Ignoring his work as the (hopefully) long forgotten “Akeem the African Dream”, One Man Gang has to go down as one of the best wrestlers to hail from Chicago, Illinois.

The Chicago native hit the heights with his feud against Dusty Rhodes in 1983, but went on to have a great career with both WWE and WCW.

One Man Gang also faced off against The Mega Powers at Survivor Series 1988, and wrestled alongside Big Boss Man as the legendary tag team “The Twin Towers”.

3. Larry Zbyszko

“The Living Legend” more than lived up to his name during his career in wrestling.

The two-time AWA World Heavyweight Champion was trained by WWE Hall of Famer Bruno Sammartino, who he feuded with in one of the best “master vs student” matches in wrestling history.

Larry Zbysko’s matches with Ric Flair and Rick Rude elevated him to one of the top heels in the world, wrestling in multiple five-star classics with his fellow legends.

He was even voted as the most hated wrestler in 1980, and the Chicago wrestler was inducted into the WWE Hall of Fame in 2015.

2. Bobby Heenan

Both a legend in the ring, at ringside and at commentary, Bobby Heenan is one of the greatest performers the wrestling business has ever seen.

He is most famous for his work as a manager in the WWE, where he managed “The Heenan Family”, containing legendary stars like Andre The Giant, Rick Rude and Mr Perfect.

The Chicago native also excelled on commentary, calling some of the classic moments in the history of wrestling, both for WWE and WCW.

His most famous call was when Hulk Hogan joined the NWO, vindicating him for a decade of hating on Hogan on commentary.

1. CM Punk

Despite his recent controversies and firing from AEW, it is hard to deny CM Punk as the greatest wrestler to ever come from Chicago.

The former ROH, WWE and AEW Champion spent 7 years out of wrestling between 2014 and 2021, although that just solidified his legacy even more for the fans.

In the WWE, he became just one of two men to win the WWE, World Heavyweight and ECW Championships (along with The Big Show), which included a legendary 434-day reign as the WWE Champion.

He revolutionized wrestling, both by his success opening the door for Indie stars to sign for the WWE and his legendary Pipe Bomb promo changing the game forever.

While he never got his coveted WrestleMania main event, Punk had legendary feuds with John Cena, The Rock and The Undertaker, to name just a few of his classic matches.

He left the company in 2014, only returning to wrestling in 2021 to sign for AEW. Here, he won two AEW World Championships before being fired in September 2023.

Despite this, his legacy remains intact as the best Chicago wrestler of all time.

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