The Web of Deceit

 How Pueblo’s “Good Ole Boys Club” Keeps Playing the Same Game

Who Wanted What?

For years, the public has watched Pueblo politics unfold like a tired rerun - same faces, same backroom loyalties, same convenient amnesia when accountability knocks. The cast of characters is all too familiar: Randy, Dan, Lori, Roger, Jerry, Gus, Regina, and Dennis - each one tangled in a web of deceit, distraction, and self-preservation that keeps the city spinning in circles.

It’s a story of ambition turned hypocrisy - and a reminder of just how deep the “good ole boys club” still runs in local government.

The Strong Mayor Shuffle

Not long ago, Randy, Lori, Dennis, and Regina all had one thing in common: they wanted to be Pueblo’s strong mayor. Each campaigned or aligned themselves toward that powerful seat, and each one lost.

Now, the same group claims to have seen the light. Suddenly, they’re all “against” the strong mayor system and insist the city needs a City Manager instead.

Convenient, isn’t it? When power slipped through their fingers, the very structure they once fought for became the problem.

Enter Jerry  - The Comeback Nobody Asked For

Their new champion? Jerry - the former City Manager whose tenure cost taxpayers nearly $700,000 in salary, severance pay, and an “undisclosed amount” he quietly handed to Dan before exiting.

But the past doesn’t seem to matter to his old friends. Roger calls Jerry his “brother from another mother.” Gus, another long-time insider and friend of Roger’s, remains close in the circle - even though Lori herself once publicly called Gus a pedophile.

Despite that tangled mess of personal and political baggage, Jerry is back in polite company - and remarkably, Regina and Dennis are leading the redemption chorus. Regina even posted on Facebook that “redemption can be a beautiful thing,” while Dennis praises Jerry as “brilliant.”

Apparently, brilliance can excuse just about anything.

A Mazda Sedan and a Memory Problem

Of course, not everyone has forgotten Jerry’s track record. More than once, his Mazda Sedan had to be pulled out of a ditch - the result, locals say, of nights spent far too deep in the bottle to keep it between the lines.

Still, here he is, being polished up as the face of “redemption” and “leadership.”

  The irony practically writes itself.

The Pattern Never Changes

What Pueblo is seeing isn’t new - it’s the same recycled leadership pattern that’s plagued the city for decades. The same people who once fought for power are now pretending to rise above it, all while clinging to their alliances and rewriting history.

They call it politics. The rest of us call it a performance - one that’s been going on far too long.

Until voters and residents demand better, the show will go on: the same names, the same excuses, the same “good ole boys” driving the city straight into another ditch - Mazda and all.

UPDATE: The Circle Tightens

Additional context has come to light regarding the financial relationship between Jerry, Dan, and Roger.

Before any of this unfolded, Roger worked for Dan, creating a chain of loyalty that predates the strong mayor debate entirely. That history matters.

When Jerry was City Manager, he authorized an undisclosed payment of city funds to Dan - a payment that has never been publicly explained in full.

Now, considering that Roger refers to Jerry as his “brother from another mother,” it raises new questions.

There is active speculation in the community that Roger may have encouraged, influenced, or pushed Jerry to direct those funds to Dan - whether as a favor, a political IOU, or a quiet reinforcement of the old guard’s power network.

No official documentation confirms the motive. But the relationships, timing, and outcomes speak for themselves.

It’s yet another example of how deeply the good ole boys club is woven into Pueblo’s decision-making, budgets, and public trust - and why transparency remains the city’s most endangered resource.