Holmberg's Morning Sickness (98KUPD):

01-15-26 – Thursdays w/Former Dallas Cowboy O-Lineman Dale Hellestrae

“Dale Brings In Some Of His Fan Mail and John Sees Through It”

Date: January 15, 2026

Overview

This episode of Holmberg’s Morning Sickness features the show’s regular and friend, former Dallas Cowboy offensive lineman Dale Hellestrae. The big focus is Dale sharing recent fan mail and John Holmberg’s deep skepticism about the sincerity and authenticity of said fan letters. The morning show crew (John, Brady, Bret Vesely, Dick Toledo) comedically dissects the earnestness (or lack thereof) behind fan letters, jokes about Dale’s football legacy, and trades personal stories about autographs, with humorous sidetracks including Dallas Cowboys locker room traditions and playful ribbing around childhood nostalgia.

Key Discussion Points & Insights

1. Dale’s “Fan Mail” and John’s Skepticism

• Dale shares a letter—purportedly from a young offensive lineman fan named Michael from Grove City College, asking for an autograph and reminiscing about Dale’s “dominant” career.
  • John immediately suspects the letter is a school assignment or even a juvenile probation requirement:

    “This is when kids who are trying to avoid juvie have to do a pick a hero and write him a letter and see if he writes back.” (03:07)

• John reads the fan letter aloud, scrutinizing details that don’t sound sincere or deeply informed:

  “You were one of the best and most dominant players in the league… You’re a long snapper.” (03:14)

• John and Bret look up the sender’s return address online, assessing the house’s worth and riffing on the fan’s (supposed) poverty for comedic effect:

  “This kid is dead broke. He lives in like the Appalachian…” (05:23)

• Dale admits he didn’t get any fan mail for a decade, but recently started receiving about five letters a month. John suggests there’s a trend of “kids going to juvie” who are required to write such letters.

2. The Ritual of Player Autographs and Super Bowl Memories

• Dale answers the fan’s question about his career highlight:

  “Probably my most dominant memory is the Super Bowl out here… Never dreamed of playing the Super Bowl here because we didn’t have an NFL team.” (04:14)

• Revisits how the 1992 Super Bowl was supposed to be in Arizona but was moved due to Arizona not honoring MLK Day.

3. The Roast: Being a “Dominant” Player and Second String Stories

• John teases Dale over being a backup:

  “If you’re second string on your own team, you’re not one of the most dominant players at your position.” (03:36)

• Dale fires back, joking about his impact:

  “Because when I came in, things opened up, John. Yeah.” (03:45)

4. Childhood Autographs—Nostalgia & Regret

• Dale’s only autograph story:

  • Rode his bike against his parents’ wishes to a parade to meet James Caan, the actor, and got his autograph—then ended up in the local newspaper the next day.

  “Literally the next day… open it up… there you are. Front page.” (17:01)

• John shares his own boyhood letter to NFL coach Forrest Gregg—who ended up sending him a large package of team memorabilia.

5. Locker Room Antics and Superstitions

• Dale reminisces about Cowboys traditions:
  • The offensive line would “grade” the outfits of skill players and coaches as they entered, with Michael Irvin (wide receiver) always wearing a tie and matching underwear, and occasionally dropping his pants to reveal the match.

    “Michael… always had underwear that matched his tie… he would stop at our row… and (drop trou) to show us.” (23:10)

  • John jokes about how “suppressed homosexuality” made the Cowboys aggressive on the field.

6. The Fame Contest: Old Players & Fan Letters

• The crew imagines a “race” between two obscure former players (like Dale and Saints RB Guido Merkens) to see who sends fan mail responses fastest.

7. Meta-Humor: The Podcast’s Real Star

• Dale and the others joke about the hierarchy of the show—who is really the star, and how Dale’s appearances have helped bolster his “Google” and “podcast” presence.

Notable Quotes & Memorable Moments

• On fan mail authenticity:
  • John: “This is when kids who are trying to avoid juvie have to do a pick a hero and write him a letter and see if he writes back.” (03:07)
• On Dale’s career:
  • John: “You were one of the best and most dominant players in the league… You’re a long snapper.” (03:22)
• On the poverty of the fan’s address:
  • John: "This kid is dead broke… The $250,000 was land nearby, like 86 acres. And then his dump of a house where he masturbates to cards of Dale..." (05:31)
• Dale on locker room rituals:
  • “You had to… grade their outfit. Michael… always had underwear that matched his tie. So then it turned into… he would drop trou to show us.” (23:10)
• Childhood autograph regret:
  • Dale: “The only one I asked for… James Caan’s the grand marshal… Literally the next day, open up [the newspaper]… there you are. Front page.” (17:01)
• John on being ignored by priests:
  • “No, the priest wouldn’t touch me… All I asked for was the opportunity to turn him down. Show a little interest.” (14:01)

Timestamps of Important Segments

• [02:24] – John reads fan letter to Dale aloud
• [03:07] – John expresses skepticism about the authenticity (“avoid juvie” letter)
• [04:14] – Dale shares his career highlight: Super Bowl memory
• [05:23] – Zillow investigation of fan’s house
• [13:19] – John’s story about autograph from coach Forrest Gregg
• [15:50] – Dale’s James Caan autograph and newspaper story
• [22:03] – Dale’s story about Michael Irvin’s matching underwear tradition in Cowboys locker room
• [23:10] – More details on Cowboys locker room rituals
• [24:06] – Scottsdale newspaper story “Local Meets Icon”
• [25:03] – Childhood appreciation of James Caan (“Brian’s Song,” “The Godfather”)

Concluding Tone and Takeaways

The episode is fast-paced, irreverent, and heavy on sarcasm. John rarely misses an opportunity to gently mock Dale’s playing days, and Dale gives as good as he gets. The show blends sports nostalgia, playful self-deprecation, and a distinctly “locker room” sensibility. The mock-analysis of Dale’s fan mail carries through the episode as a running joke, with a subtle undertone about the realities of fame for second-string NFLers versus legends.
Perfect for listeners who enjoy funny, unfiltered banter about sports, fame, and the weirdness of fan interactions.