Cutting-Edge Benefits Podcast

COBRA: The Most Expensive Letter You’ll Ever Get


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This episode tackles one of the most misunderstood—and financially painful—moments in healthcare: COBRA coverage.

Tom Quigley explains why that official-looking COBRA letter often becomes the single most expensive piece of mail someone will ever open, and why most people panic, overpay, and make the wrong decision simply because no one ever explained their options.

The takeaway is simple and powerful: COBRA is not automatic, not mandatory, and very rarely the best first move. If you understand the timing and the math, you can protect yourself without lighting money on fire.

Tom breaks it down in plain English:

  • While employed, you only paid your portion

  • Your employer was quietly paying the rest

  • COBRA = 100% of the premium, plus admin fees

Example:

  • Family plan costs $3,500/month

  • Employee paid $500

  • Employer paid $3,000

  • On COBRA, you pay the full $3,500

Tom:

“That employer contribution? That was part of your salary.”

  • The employee who leaves pays it

  • Employer has zero ongoing obligation

  • COBRA exists only to allow continuation—not affordability

Tom points out something critical:

“The need for COBRA is almost zero today because of the ACA.”

This is one of the most valuable insights of the episode.

COBRA gives you:

  • 60 days to elect

  • Coverage is retroactive if you elect later

Tom’s strategy:

  • Don’t pay COBRA immediately

  • Use the free window

  • If nothing happens → switch to an ACA plan

  • If something major happens → elect COBRA retroactively

Tom:

“You get two free months of insurance if you don’t use it.”

This alone can save thousands of dollars.

Once you’re no longer employed:

  • Employer is no longer contributing

  • Your income often drops to zero

  • You may qualify for very strong ACA subsidies

Tom:

“I see people get zero-premium ACA plans after quitting a job.”

COBRA doesn’t block this.
You just need to not rush.

The most common (and costly) error:

  • Assuming COBRA is the only option

  • Paying immediately out of fear

  • Never comparing ACA pricing

Tom:

“It’s a financial mistake—nothing more.”

Tom reviews alternatives:

  • ACA marketplace plans (often far cheaper)

  • Subsidies based on reduced income

  • Faith-based sharing plans (with strong caveats)

On faith-based plans:

“It’s like living on a prayer—no guarantees.”

COBRA can be the right move if:

  • COBRA premium is lower than ACA options

  • You’re mid-treatment

  • Networks or doctors are critical

Tom:

“It’s always a math problem. Do the math.”

Tom doesn’t sugarcoat reality:

  • Healthcare without strategy leads to financial disaster

  • COBRA panic decisions compound the problem

  • Education prevents unnecessary loss

Tom:

“When people don’t do the math, the trains collide.”

Neil raises the broader issue:

  • Healthcare costs are exploding

  • For many, this is the largest tax increase they’ll face

  • It hits especially hard after job loss

Tom:

“They have no one but the person in the mirror to blame—because the tools exist.”

Tom makes it clear:

  • Anyone leaving a job should call before acting

  • ClaimLinx walks people through:

    • Timing

    • Subsidies

    • ACA options

    • When (and if) COBRA makes sense

Tom:

“It’s coaching, not selling.”

  • COBRA is expensive because you’re paying your salary benefit

  • You do not have to elect COBRA immediately

  • You get a free decision window

  • ACA subsidies often crush COBRA pricing

  • COBRA is sometimes right—but rarely first

  • This is a math problem, not an emotional one

“COBRA is the most expensive letter you’ll ever get.” — Tom Quigley

“You get two free months of insurance if you don’t use it.” — Tom Quigley

“COBRA isn’t mandatory. Panic is.” — Tom Quigley

“Healthcare is a math problem. When you ignore the math, you lose.” — Tom Quigley

👉 Visit: https://www.ClaimLinx.com
📞 Schedule a Call: Leaving a job? Talk to Tom before electing COBRA
🎧 Subscribe: Cutting Edge Benefits Podcast & The Neil Haley Show



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Cutting-Edge Benefits PodcastBy Claimlinx