Podcast Summary

Podcast: Holmberg’s Morning Sickness
Episode: 08-21-25 – Thursdays w/Former Dallas Cowboy OLineman Dale Hellestrae
Date: August 21, 2025
Host(s): John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo
Guest: Dale Hellestrae (Former Dallas Cowboys O-lineman)

Episode Overview

This episode of "Thursdays with Dale Hellestrae" dives into sports nostalgia, focusing on the Dallas Cowboys’ legacy, NFL pensions, the culture of public salaries for athletes, and lighthearted banter about aging, family, and end-of-life decisions. The hosts reminisce about the Cowboys’ Super Bowl years, discuss Netflix's new Cowboys documentary, reflect on Dale's career trajectory, and mix in dark humor about mortality and mental health, all while maintaining the show’s irreverent, comedic tone.

Key Discussion Points & Insights

1. Cowboys’ Glory Days, The Netflix Documentary, and 30 Years without Success

• Cowboys’ Dominance & the “Forgotten” Dynasty

  • Dale notes that anyone under 40 might not remember the Dallas Cowboys’ glory years or even their last NFC Championship appearance. (04:41)
  • "For all you young folks...40 and younger don't know that the Cowboys used to be in Super Bowls." - John Holmberg (04:41)

• Reflections on the Netflix Docuseries

  • Dale discusses being included in the new Netflix Dallas Cowboys documentary.
  • He recalls forgetting some wild stories, only to have them resurface during interviews and while rewatching. (06:16)
    • "There's a lot... Like this guy's writing a book about Troy. He called me...and he brought up some stories that I'm like, oh yeah, Michael Irvin stabbed that guy." – Dale Hellestrae (06:16)
  • Dale is anxious as the series hasn’t reached the “troubled years” (i.e., White House, Deion years, team controversies).
    • The documentary so far only covers Jerry and Jimmy, their buy-in, and the early '90s.

• Jerry Jones’ Legacy and Team Decline

  • Both discuss Jerry Jones as Cowboys owner—from his lucky oil strike to firing Tom Landry and his refusal to step aside as GM.
  • "As smart as he is... you'd think he'd realize, I need to get somebody here to run the football side." – Dale Hellestrae (10:12)
  • Cowboys' franchise value: up from $140M to an estimated $15-20 billion. (10:37)

• A Legacy that Won’t Die (Literally)

  • They poke fun at the Cowboys’ inability to win since Dale left, with frequent reminders of the 30-year NFC Championship drought.

2. Dale Hellestrae’s NFL Memories & Unique Position in Football History

• The “Dale Curse” & Team Transitions
  • Dale jokes that teams suffered or flourished when he left or joined, e.g., SMU’s death penalty/post-Dale Cowboys success.
  • "Michael and Troy were with the Cowboys before they made the blockbuster trade for me...then I leave in 2000, and guess what? Have they had any success?" – Dale Hellestrae (16:43)
• Interactions with NFL Legends
  • Hellestrae tells a story of texting Jimmy Johnson about trades and being one of his “best”—prompting an Al Davis six-pack beer joke. (15:36–15:55)
  • When asked about friendship with Johnson, Dale deadpans: "Friends is a strong word...he's an isolationist." (16:02–16:09)

3. The Culture of Public Salaries for Athletes

• NFL Pensions and Public Curiosity
  • Dale breaks down his NFL pension: about $800 per year played, adding up to nearly $10K extra annually for his lengthy career. (17:29–18:12)
  • Early NFL pensions paid out far less—just $50/year played; this has improved in recent years.
  • Both reflect on the weirdness and discomfort of athletes' salaries being public record.
    • "I was raised that you never ask a man what he makes. Ever." – John Holmberg (19:21)
    • "Why should people know how much I weigh or how tall I am or...my salary?" – Dale Hellestrae (19:40)

4. Mortality, Aging, and Family (with Dark Humor)

• Electroshock Therapy and Mental Health Jokes

  • The group riffs on an anecdote about Brady’s grandmother undergoing electroshock therapy, spinning it into jokes about family secrecy, country clubs, and institutions of a bygone era. (20:19–22:48)

• End-of-Life “Contingency Plans”

  • Talk veers into uncomfortable hypotheticals about aging, pondering when they'd want a loved one to “pull the plug” if incapacitated.
    • Hellestrae: "I'm contemplating giving both my daughters one of those cyanide pills or whatever that can kill..." (23:51)
    • Holmberg: "My dad and I have a deal...if either of us are told by a doctor he'll never wipe himself again... we're going to do the pillow over the other guy's face." (24:45)
  • Ultimately both echo, with some sincerity behind the laughs, that they're not interested in life if incapacitated, but remain hopeful for healthy, active aging.

Notable Quotes & Memorable Moments

• On the Netflix Documentary’s Nostalgic Value:

  • "It's great...for my daughters, son-in-law...watching some of this stuff, and I think a lot of people forgot...how good we were. We were great." – Dale Hellestrae (11:33)

• On NFL Pensions:

  • "When I first got in the league in '85...the NFL pension was $50 per year you played. If you play four years...you get $200 a month when you turn 55." – Dale Hellestrae (18:12)

• On Team Loyalty and Football’s Ruthlessness:

  • "I leave SMU, they get the death penalty. ... I leave the Cowboys, no more Super Bowls, I leave the Ravens, and they won one." – Dale Hellestrae (15:03-16:03)

• On Aging and Control:

  • "I'm contemplating giving both my daughters one of those cyanide pills or whatever...so the first time they have to change me...give me the pill." – Dale Hellestrae (24:00)
  • "My dad and I have a deal...if either of us are told...he'll never wipe himself again...pillow over..." – John Holmberg (24:45)
  • "Age is just a number. It's what you do. You got to keep moving." – John Holmberg (25:17)

Key Timestamps

| Timestamp | Segment/Topic | |-----------|----------------------------------------------------------------| | 01:44 | Dale’s first appearance; intro to Cowboys standup and doc talk | | 04:41 | Discussion: Younger fans don’t recall Cowboys’ Super Bowl era | | 05:31 | Dale on getting random texts about Netflix documentary | | 06:16 | Forgotten wild stories from the Cowboys’ heyday | | 07:21 | Preview of upcoming, more scandalous documentary episodes | | 10:12 | Jerry Jones, ego, and refusal to cede football ops control | | 14:59 | The “Dale Curse” and Cowboys’ drought | | 17:29 | NFL pensions explained | | 19:21 | Public salary discussion & athlete privacy | | 20:19 | Brady’s family & electroshock therapy story | | 23:51 | Cyanide pill jokes; end-of-life "deals" | | 25:17 | "Keep moving" – positive aging wrap-up |

Tone & Style

The conversation is rapid-fire, irreverent, and peppered with both affection and ruthless zingers. Holmberg leads with snark and skepticism, while Dale matches with laconic deadpan and self-aware exaggeration. Adult humor and darker subjects are handled with tongue-in-cheek camaraderie, never letting the mood slip from wry, locker-room storytelling.

For First-Time Listeners

Even if you’ve never tuned in before, this episode offers a crash course in locker room nostalgia, football inside-baseball, and the uniquely comedic worldview of Holmberg and company. You’ll hear behind-the-scenes NFL stories, aging athlete realities, and the kind of teasing only old friends can get away with—plus a few not-quite-PC asides about football, family, and facing the inevitable.