Dan Bernstein Unfiltered – Episode Summary Episode: "Chicago Cubs Panic, Old Patriots Weirdness Tom Brady & Bill Belichick, Smokin' Jay's Got a Gun"
Date: August 28, 2025
Host: Dan Bernstein, with Matt Abbatacola
Podcast: Dan Bernstein Unfiltered (312 Sports)

Overview

This episode of Dan Bernstein Unfiltered delivers a characteristically irreverent and sharp take on the current state of Chicago sports, with particular focus on the Chicago Cubs’ latest woes, the omnipresent shadow of ex-Patriots Tom Brady and Bill Belichick on the NFL, and the off-field troubles (and hair) of former Bears quarterback Jay Cutler. The conversation weaves from statistical deep dives and serious sports analysis to hilarious tangents about Cracker Barrel, Topgolf parking lots, and the minutiae of rye bread vs. cracked ham.

Key Discussion Points & Insights

1. Old Patriots Weirdness in the NFL

Begins: 03:33

• Tom Brady’s Broadcasting Dilemma
  • The NFL has relaxed the so-called “Tom Brady rules” that previously barred Brady, as an NFL owner, from attending production meetings as a Fox commentator.
    • Dan: "Fox gave Tom Brady $375 million over 10 years to be bad at analyzing games." (03:55)
  • Brady continues to underwhelm in the broadcast booth, especially compared to Greg Olsen, who Dan praises as "100 times better." (05:43)
  • Frustration with Fox prioritizing celebrity over quality broadcasting:
    • Matt: “There is absolutely no reason why Tom Brady should be in a broadcast booth as an owner of an NFL team, period.” (07:56)
• Belichick’s Off-Field Circus
  • Media obsession with Bill Belichick’s personal life, including the antics of girlfriend Jordan Hudson, who is “trademarking Gold Digger.” (07:14)
  • Dan terms the ongoing drama "Old Patriots Weirdness (OPW)," arguing it haunts NFL fans even after the dynasty’s demise:
    • “It really is. It’s like a poltergeist.” (11:58)
  • Parallels drawn between the Patriots’ lingering shadow and the never-ending Dallas Cowboys hype cycle—comparing ESPN and Cowboys to “marketing businesses that happen to have sports/football.” (09:18)

Notable Quote

• Dan: "Between all the genuflecting at the altar of Tom Brady and all this side-glancing at whatever's going on in Chapel Hill with Bill and this succubus that comes in at night and does things to... It just nags at you a little bit." (13:19)

2. Chicago Cubs: Reality Check & Playoff Math

Begins: 17:19

• Recap of the recent “ugly” Cubs loss: "It was an ugly night for Colin Ray. Ugly night all around. Bad offense, bad defense." (17:19)
• Discussion of advanced standings metrics, specifically Clay Davenport’s adjusted standings/third order record. (18:18)
  • Brewers now surpass Cubs in third order record.
• Projection of playoff odds:
  • “FanGraphs has them at 7.2% chance to win the division, 92.3% chance to clinch a wild card.” (21:41)
• Playoff format breakdown and importance of hosting in the wild card slot.
• Riff on Cubs lost momentum after "being the best team in baseball at the All Star break" and Brewers’ surge.
• Analysis of wild card paths, schedules, and the key formula for playoff success:
  • "You know what wins the World Series? Home runs and strikeouts. Ball go far. Team go far." (25:11)

Notable Moment

• Recap of the “Bernstein kiss of life”—after they criticized Nico Hoerner’s lack of power, he homered in the next game (20:38)
  • Matt: "[After Nico hoerner's homer] He’s like, f*** you, Dan Bernstein Unfiltered, take that!" (21:11)

3. Jay Cutler: “Smokin’ Jay’s Got a Gun”

Begins: 36:45

• Discussion of Jay Cutler’s recent sentencing (four days in jail) from a DUI charge.
  • Dan reads AP details: Cutler rear-ended a car, was clearly intoxicated, tried to bribe the other driver with $2,000 ("How you get that number? My guess is that's the amount of cash he had." - 38:25), and police found two firearms in his vehicle, including a loaded pistol.
• Matt laments Cutler’s decisions but also sympathizes—calls for Cutler to get his life together and jokes about his famously good hair.
  • Matt: “Just, dude, like, get your life together.” (37:15)
• Riff on how much cash Dan and Matt carry, with Dan astonished at Jay rolling with “two grand” and “two guns.”
• Sarcastic thread about Topgolf Naperville’s frequent weapons busts (41:33)—calls for the National Guard to patrol the parking lot for weapons left in cars.

Notable Quotes

• Dan (on why Cutler offered $2k): “My guess is that's the amount of cash he had.” (38:25)
• Matt: "Why are you rolling around with guns? ... What are you doing with a gun?" (40:33)

4. Cracker Barrel, Toothpick Philosophy, and Rye Bread

Begins: 52:08 (Cracker Barrel segment); 53:41 (Toothpick Story); 57:03 (Rye Bread Segment)

• Riff on Cracker Barrel’s controversial logo change and its weird spot in the culture wars. Both hosts agree: the old logo is simply a better logo—nothing political about it.
  • Dan: “It has nothing to do with heritage or crackerism or anything else.” (48:47)
• Vivid reminiscence about the Cracker Barrel “peg game”—including the original, now-sanitized, scoring rubric (“if you leave three, you’re just plain dumb…”), and Dan’s one-time enjoyment of their “real” turnip greens and unique toothpicks.
• Tangent about thrifting for a backdrop bookshelf, buying toothpicks as a 23-year-old, and the passage from “Cracker Barrel” to “rye bread superiority.”
  • Matt: "You’re a 23-year-old kid and you’re like, I need toothpicks. You’re so weird." (54:33)
• The show closes on an affectionate discussion of childhood food memories—Bakers Square, Poppin’ Fresh, black rye patty melts, and the best use of rye and cracked ham.

Memorable Moment

• Matt volunteers to take Dan to Cracker Barrel for the second time in his life, illustrating their “Chicago guy, real people” rapport. (55:38)

Additional Highlights and Humorous Asides

• The prevalence of “airport bar” sports content and disdain for national yelling shows. (09:18)
• "Old Patriots Weirdness" (OPW) established as a running bit. (11:58, 16:07)
• Extended, satirical contemplation of carrying firearms and heavy weaponry to Topgolf, and the need for “federal troops” for mulching and garbage collection. (41:34, 43:11)
• Playfully mocking Chicago sports radio bits, including the “Chicago Sports Sandwich” and steak-and-bacon sandwiches at Waffle House. (30:41)

Timestamps for Major Segments

| Topic | Timestamp (MM:SS) | |---|---| | Opening banter, sponsor plugs | 01:33 | | How Tom Brady keeps getting privileged broadcast opportunities | 03:32 | | “Old Patriots Weirdness” (OPW) – Belichick drama | 07:09 | | Comparison: Patriots vs Cowboys, ESPN as marketing empire | 09:18 | | "Airport bar sports" rant | 09:33 | | Cubs reality check, advanced standings, playoff odds | 17:19 – 28:20 | | Cubs schedule, path to 96 wins | 27:14 | | Thrifting, bookshelf, Goodwill Trubisky jersey | 35:40 | | Jay Cutler DUI/guns scandal | 36:45 – 44:45 | | Topgolf Naperville guns running joke | 41:33 | | Cracker Barrel culture/branding tangents | 47:37 – 53:41 | | Toothpicks, rye bread, deli sandwich nostalgia | 53:41 – end |

Notable Quotes

“Between all the genuflecting at the altar of Tom Brady and all this side-glancing at whatever’s going on... It just nags at you a little bit.”
– Dan Bernstein (13:19)

“It really is. It’s like a poltergeist... The OPW is following us around and haunting us in some way.”
– Dan Bernstein (11:58)

"There is absolutely no reason why Tom Brady should be in a broadcast booth as an owner of an NFL team, period."
– Matt Abbatacola (07:56)

"You know what wins the World Series? Home runs and strikeouts. Ball go far. Team go far."
– Dan Bernstein (25:11)

Tone & Style

True to Dan Bernstein’s legacy, the discussion is salty, brisk, honest, with plenty of inside jokes and detours that pull the curtain back on Chicago fandom. Matt ably punctuates the conversation with dry, observational comedy—they riff together like old friends, frequently circling from analysis to Chicago-guy tangents and back.

Perfect for fans wanting unfiltered sports commentary, biting humor, and authentic Windy City perspective on the state of the Cubs, NFL, and the always-entertaining world around Chicago sports.