Caylor Steps Up To Challenge Chirico For Mayoral Election

It’s not easy defeating an incumbent, even an incompetent incumbent, but it’s especially difficult to defeat a successful, competent incumbent. That’s the position Richard ‘Rocky’ Caylor finds himself in, trying to defeat Naperville Mayor Steve Chirico. If this was a fist fight, then how can you bet against a guy named ‘Rocky’ considering undefeated heavyweight champion Rocky Marciano, or Rocky Balboa. But this most likely is Rocky from ‘Rocky and Bullwinkle’. Caylor definitely has his work cut out for himself. Smart money would be on Chirico to blow away Rocky the challenger.

There are similarities between the candidates. Both names start with ‘C’, both own successful businesses, both live in Naperville, neither has lost a mayoral election, (first time running for Caylor), both think they can lead the city, though only Chirico has proven it.

This is Chirico’s second run for mayor. In 2015, it was a level playing field when all four candidates were running to replace retiring mayor George Pradel. Chirico won the election with 60.5% of the vote, followed by long-time mayoral-election loser Doug Krause with 29.3%, Marty Walker 7.6%, and Jim Haselhorst with 2.5% of the vote.

You have to give former councilman Doug Krause credit for coming in 2nd place in five mayoral election bids (1995, 1999, 2007, 2011, and 2015, surpassing the NFL Buffalo Bills head coach Marv Levy four straight Super Bowl losses. Should Caylor lose the election, he would have quite a way to go to match Krause’s record

Mayor Chirico’s campaign war chest is bulging, with well over $100,000 in contributions, and more dollars pouring in daily. As we get closer to election day, Chirico currently has enough money to buy every eligible voter a chocolate dipped Dairy Queen ice cream cone, with enough money left over to have a huge election night celebratory victory party at Hugo’s, and still have campaign funds leftover to seed his next mayoral election in 2023.

Chirico is probably very appreciative that Caylor decided to step into the ring to challenge him. What’s the fun in not having an opponent. It would be like the Cubs suiting up for a game and the Cardinals or White Sox not showing up to play, or Chirico shadow boxing in his back yard. That’s no fun.

And as for that fist fight between Rocky and Chirico, you can’t count Chirico out of that either, considering he was a Naperville High School champion wrestler; Rocky’s done once Chirico gets his hands on him.

Show 4 Comments


  1. Mike Marek

    As for that fistfight you surmise, you note Chirico was a high school “champion” wrestler.

    Caylor’s a United States Marine.

    You going to bet against a US Marine?

    • watchdog

      It would be even better if the U.S. Marine was a high school ‘champion’ wrestler.

  2. BDWeiser

    So….WD it’s time for you to speak (find) the truth!! Based on some of your recent posts… have become “one of them.” You’ve enamored Steve, gulp, Naperville’s mayor, for too long. It’s time you look beyond his bs & speak the truth and more importantly find the truth..
    Why would ANYONE vote for this man again? He’s rude crude and obnoxious. He had no reason to run for Council or Mayor—–unless, of course, he had an ulterior motive?
    HHHHHMMMMMM……. The property @ 7th & Washington laid dormant for many-a-year & now there is a big bad building there once he became mayor & his company now owns it. Oh ok his children do…. The property near Tabor Hills has his name all over it and it continues on. He quieted the critics over his brother’s dilapitated property on Emerald—how’d that end?. He has pushed & pushed to get 5th Avenue developed too quickly which caused members of Council to curtail his activity just as quickly. They were onto his game HHHHHMMMMM…… what connections does he have with that company??? Is that why certain council member chose not to run again? Is that why he moved someone who was running for council to the Settlement board so he could get his yes-men on council?? And, now….now, he pays big $$$ to find ‘dirt’ on his opponent!! HHHHHMMMMMM….. are we in Chicago or Naperville?? Absolutely disgusting.
    So Watchdog. What are you going to do about this sad sack for a mayor? Are you going to preen about his days as a HS wrestler or are you going to face the facts and realize it’s all about Steve?
    Save Naperville. Vote for anyone other than the man who wants it all for himself.

    • watchdog

      The good news BDWeiser is that you get a vote, I get a vote, everybody gets a vote. It doesn’t get any better than that.

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