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  • The Wiseguy’s Road: Jimmy Cicero’s Long Strange Trip Through Wrestling’s Underbelly

The Wiseguy’s Road: Jimmy Cicero’s Long Strange Trip Through Wrestling’s Underbelly

Posted on September 3, 2025 By admin No Comments on The Wiseguy’s Road: Jimmy Cicero’s Long Strange Trip Through Wrestling’s Underbelly
Old Time Wrestlers

Professional wrestling has always been a business built on survivors—men and women who find ways to keep their boots laced long after the spotlight fades. And few embody that spirit better than Matthew Bowman, better known by the name that has rattled around dingy armories, smoke-filled bars, and even the bright lights of ECW: “Wiseguy” Jimmy Cicero.

He isn’t Hulk Hogan. He isn’t Stone Cold Steve Austin. But for three decades, Cicero has been the guy keeping the car running while everyone else was arguing about who got shotgun. He’s wrestled for ECW, appeared in the WWF as the guy on the other side of the squash, and headlined countless indie shows in front of crowds small enough to fit into a 7-Eleven. Yet somehow, he’s still here, still snarling, still wisecracking, still throwing hands.


Koloff’s Pupil

Cicero wasn’t supposed to be here. Born in ’69, trained by none other than Ivan Koloff—yes, the same Russian Bear who once ripped the WWWF Championship off Bruno Sammartino—Cicero learned early that charisma was just as important as a headlock. He broke in during the early ’90s, when the business was at its most transitional: Hulkamania fading, Attitude not yet born, and territories gasping for breath.

By 1994, Cicero was already picking up gold in Carolina Championship Wrestling Alliance with a tag team called The Country Club. It sounds classy—white linen, golf clubs, champagne on ice—but in reality, it was more “two dudes in satin jackets fighting for $50 and a hot dog.”

He later pivoted into The Rat Pack with Brian Perry, grabbing tag titles and earning a reputation as a guy who could talk, bump, and keep the crowd entertained even when the ring ropes looked like they’d been strung together at a hardware store sale.


The ECW Years: Tables, Chairs, and a Bruised Ego

1996 dropped Cicero into Extreme Championship Wrestling, the Philadelphia-based carnival of blood and broken furniture. He wasn’t a Paul Heyman project, but he found himself in there with the likes of Balls Mahoney, Spike Dudley, and even Taz. That’s like playing pickup basketball and realizing your opponent is Shaq in a bad mood.

Cicero did what journeymen always do: survive. Take your bumps, hit your spots, and leave with your dignity intact—even if your body looks like it went through windshield glass. He even snagged the MEWF Mid-Atlantic Championship that year, proving that while ECW’s lights were bright (and flickering), he could still be the guy on top in other territories.


Gold Everywhere, Except the Big Leagues

If you were watching wrestling in the late ’90s, you probably saw Cicero and didn’t even know it. On an episode of Raw in January 1998, he and Lance Diamond got fed to Kurrgan in a handicap match. WWF needed bodies; Cicero obliged. It wasn’t glamorous, but it was a paycheck, and a chance to say, “Yeah, I worked the Garden.”

But where Cicero truly thrived was in the independents. He was a belt collector before that phrase was cool. NWA 2000 Heavyweight Champion. IPWA Heavyweight and Tag Team Champion. Maryland Championship Wrestling champ multiple times, trading gold with the likes of The Headbangers, Stevie Richards, and even Jerry Lawler.

The guy had more straps than a Guitar Center wall display.


Blood Feuds and Family Business

Cicero’s career wasn’t just about chasing gold. It was about fights that made towns care. His run in Pittsburgh’s Renegade Wrestling Alliance gave fans a six-year stretch of wars, including a Dog Collar Match with Bronco McBride that left enough blood on the canvas to make a butcher queasy.

And then there’s the family angle. Cicero didn’t just wrestle—he brought his son, Michael Bowman, into the business as Dr. Jack Cicero. Together they won tag titles, proving that wrestling is one of the few industries where father-son bonding can include steel chairs and suplexes.


Reinvention in Alabama

By 2021, most guys Cicero’s age were sipping light beer on their couches, yelling at Raw like it owed them money. Not him. He rolled into Alabama, rebranded as Lord James Cicero, and declared himself the “Lord of Alabama.” If that sounds absurd, that’s because it is—but absurdity is wrestling’s lifeblood.

Backed by his heel stable, “The Lord’s Army,” Cicero tormented Rocket City Championship Wrestling, feuding with local heroes and even beating Super Crazy in a controversial match at WrestleCon 5. Yes, Super Crazy from ECW. Yes, in 2021. Wrestling, baby—it never dies, it just gets weirder.


Trainer, Mentor, Wiseguy

Cicero’s résumé isn’t just about titles or feuds. It’s about influence. He ran the IPWA Wrestling School, teaching the craft to guys like Christian York and Joey Matthews, who went on to bigger stages in Impact and WWE. Today, he continues that work at Rocket City’s training academy, passing down Koloff’s lessons with his own Wiseguy spin.

It’s fitting. He’s always been the guy behind the guy. The hand that steadies the ship while others grab the spotlight. The one who makes sure the kid knows how to bump, how to sell, how to keep his mouth shut in the locker room until he’s earned the right to open it.


The Legacy of the Wiseguy

Jimmy Cicero will never headline WrestleMania. He won’t get a 10-part docuseries on Peacock, narrated by The Rock. But walk into any indie locker room from the Carolinas to Pittsburgh to Alabama, and mention his name. You’ll hear stories—about his promos, about his willingness to bleed, about his ability to make green kids look like a million bucks.

That’s legacy. Not the pyrotechnics, not the merch checks, but the grind.

Wrestling has its icons, its megastars, its household names. And then it has its Wiseguys—the ones who remind us that the business doesn’t run without the journeymen, the belt collectors, the guys willing to work anywhere, anytime, against anyone.

Matthew Bowman, Jimmy Cicero, Lord James—call him what you want. He’s proof that wrestling isn’t just about who’s on top. It’s about who’s still standing when the dust clears. And Cicero? He’s still standing.

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