The Owner’s Trap – Loyalty That Cost the Franchise

THE WEIGHT OF RESCUE

The Owner’s Trap – Loyalty That Cost the Franchise

Sentiment kills systems.

Some people inherit a team. Others build one from the ground up. But no matter how you came to own the keys, your job as an owner, president, or general manager is the same: protect the system, not your personal attachments.

And yet, this is where so many leaders fail.

They confuse loyalty with leadership. Sentiment with strategy. And in doing so, they trap themselves in cycles of underachievement—all because they couldn’t bring themselves to say “enough.”

We’ve seen it happen in real time. Look no further than Jerry Jones. He built the Dallas Cowboys into a global brand—America’s Team. But for over two decades, they’ve been stuck. Not because of talent. Not because of money. But because the one man who holds the keys can’t seem to let go of his own decisions. Jerry’s loyalty to legacy—whether it’s Jason Garrett’s extended run, or the ongoing trust in players who consistently underdeliver—has turned the Cowboys into a monument of potential with no postseason legacy to show for it.

Then there’s James Dolan and the New York Knicks. A billionaire who’s turned a marquee franchise into a punchline by protecting his inner circle and pushing out critics. Loyalty to dysfunction. Power without accountability. Culture poisoned from the top down.

But this isn’t just a pro-level problem.

It’s happening in colleges, too—boosters and boards protecting head coaches past their prime, pouring millions into football programs that haven’t produced results in years. In high schools, legacy hires and old-guard coaches cling to positions while the program suffers—because no one wants to deal with the fallout of telling them the truth.

And let’s be honest—this happens in business, too. Founders hold on to “original team members” long after they’ve outgrown the vision. Managers promote friends over performers. Owners let sentimental ties dictate who stays and who leads, forgetting that leadership requires distance, not dependency.

Leadership isn’t about who you like. It’s about who moves the mission.

THE OWNER'S RESET PLAN

Three Moves to Break the Loyalty Trap:

1. Detach Performance from Personal Connection. Just because you recruited them, built with them, or won with them once doesn’t mean they still belong. Evaluate based on now, not nostalgia.

2. Audit Your Inner Circle. Ask: Who challenges me? Who drains me? Who’s protected but unproductive? Build a system, not a family reunion. Loyalty is earned—continually.

3. Create Sunset Pathways, Not Sudden Exits. Offer mentors, legacy roles, or transitional plans for veterans. Respect doesn’t mean unlimited access. It means giving them dignity without handing them the reins forever.

Bonus: Set a rule: If your gut says “this isn’t working” for more than one season, act. Delaying action for comfort only guarantees regret.

Final Word: You don’t owe permanence to anyone who’s stopped building. Your job is to preserve the program—not protect egos. That’s not betrayal. That’s leadership.