Barstool Pick Em – Week 5: “RICO BOSCO CRIES & PRODUCER OWES DAVE PORTNOY $100K”

Date: September 25, 2025
Hosts: Big Cat (Dan Katz), Dave Portnoy (“Pres”), Rico Bosco
Theme: A riotous breakdown of Pick Em’s Week 5, marked by emotional highs and lows: Rico Bosco’s infamous near-cry, a $100k parlay controversy, unit-shaming debates, office drama, and the gang’s unfiltered takes on the week’s college football slate.

Episode Overview

This episode is a classic example of the chaos that makes Barstool Pick Em a cult favorite: sharp betting talk interwoven with the crew’s personal conflicts, gambling-related ribbing, and unfiltered banter. Rico Bosco’s emotional spiral over a questioned wager sets the tone before the show delves into the season’s biggest wins, losses, and beefs inside the Barstool office—culminating with potentially $100,000 on the line and furious accusations over a missed early cashout.

Standings and Bet Bragging/Bickering

[01:29 – 06:16]

• Standings Update:

  • Dave leads with 57%, Big Cat at 53%, Rico trails at 41%.
  • Quickly devolves into the entire crew debating picks legitimacy, amid jokes about Bob Diaco and parlays.
  • Quote:
    • "Every...I agree, actually. Ev had a good line. He goes, 'You took the hardest route to get there.'" – Big Cat [02:49]

• Rico’s Florida State Bet Drama:

  • Dave and Big Cat praise Rico for a ballsy live bet (Florida State over 20.5 second half), but quickly tease him about whether he actually placed the bet—as he refuses to show the betting slip.
  • Rico gets defensive, sparking arguments about “gotcha culture” and mock accusations of “unit shaming.”
  • Quote:
    • "I’m not 100% sure you bet it." – Dave [06:24]
    • "Then open with that clip, and then that’s fine." – Rico [06:27]

• The “Unit Shaming” Saga:

  • The group relentlessly teases Rico about possibly betting a comically low amount (one cent?) just for proof.
  • Rico finally admits it’s barely enough for a sandwich “for the whole party!” ($12) [13:42].
  • Quote:
    • "It’s a little guy. Yeah, you could [buy a sandwich]. 100." – Rico [13:40]
    • "That little guy's a real guy." – Dave [14:21]
    • "We're literally crying over spilled milk." – Big Cat [10:52]
  • Ends with everyone agreeing it was a “real” bet, but only after Rico nearly cries from the pressure.
  • Memorable Moment:
    • Rico’s pain and frustration mount to an almost-tearful moment over being doubted—both hilarious and awkward.

Tangents and Barstool Office Drama

[16:06 – 24:42]

• Producer Jackie’s Oktoberfest Vacation Debacle:

  • The gang roasts producer Jackie for skipping NFL Week 2 (and his gambling obligations) to attend Oktoberfest in Germany.
  • Dave blames Jackie for missing an $80,000 voided parlay (due to an injury situation and a missed DraftKings cashout), a running joke that balloons to $100K.
  • Quote:
    • "You owe me probably $75, $80 grand, Jack. You honestly do...because the kicker came in." – Dave [21:45]
    • "Jackie's taking vacation in fucking week two of the NFL season because somebody in Chicago had a great opportunity. What a joke this league is." – Dave [23:41]

• Rico’s Milk Incident:

  • Amidst the tension, Rico recounts being “forced” to drink milk during a stream, leading to fake/real puking and a skin rash.
  • Quote:
    • "It took him 15 minutes to drink it. He was puking. Fake puking. Possibly. Some were saying, not me." – Ev [09:18]
    • "I hate milk." – Rico [10:29]

Game Debates, Hot Takes & Classic Barstool Banter

Illinois vs. USC (Big Noon Kickoff Pick Em Game)

[31:39 – 34:39]

• Consensus:
  • Dave likes Illinois and the over, citing schedule troubles for USC and pride factor for Illinois.
  • Big Cat agrees on the over.
  • Rico sticks with USC minus the points, believing they’re a superior squad.
  • Notable Exchange:
    • "They played 11pm Eastern... now they play noon Eastern on Saturday. The line is six and a half the over under 61 and a half." – Big Cat [31:52]
    • "I think Illinois will stay in this game." – Big Cat [33:21]
    • "I'll take USC minus the six and a half." – Rico [33:36]

Ryder Cup Golf & “Caring” About National Pride

[34:54 – 36:19]

• Dave admits not caring about the Ryder Cup, much to everyone else’s shock.
  • "I just don't. I don't put American pride in golf." [35:01]
  • Quick aside about team bets, office-wide parlays, and who’d risk what in the Barstool office.

Key Game Picks: Debate & Trash Talk

[36:40 – 52:53]

• Washington vs. Ohio State:

  • All agree: Washington is live, possibly to win outright.
  • Quote:
    • "This line is screaming. No, I agree with you." – Dave [38:46]
    • "I like the Huskies outright." – Dave [39:12]
    • "I'll take the over. I think Washington can score." – Rico [40:00]

• LSU vs. Ole Miss & The Lane Kiffin Daughter Distraction:

  • Crew dismisses the idea that Lane Kiffin’s daughter dating LSU’s linebacker is a distraction—calls story “one of the great non stories of all time.”
  • Quote:
    • "If you have a daughter, you want her to date the star football player, not a wiggle dicker." – Dave [41:07]

• Oregon vs. Penn State (“Duckies” vs “State Penn,” and Ridership Wars):

  • Rico delivers a fiery, stat-supported, impassioned Duckies promo (his "mortal").
  • Massive back-and-forth on loyalty, ridership, and Barstool office politics about showing up in rival school gear.
  • Quote:
    • "Franklin against ranked 12 and 26, 3 and 17 against the top 10, 1 and 14 against the top five... They win the game on the field..." – Rico [48:09]
    • "Stop making witnesses who know things go disappearing in their car." – Rico, roasting James Franklin [49:44]

• Alabama vs. Georgia:

  • Dave: Bama will win straight up, backs Simpson as a real QB (possible Heisman talk).
  • Rico: Takes the under, citing Kirby Smart's Bama struggles.
  • Big Cat: Takes the over, expecting points.
  • Quote:
    • "I like Alabama here. I think Alabama wins the game. I think it's high scoring, but I think Alabama's... they're better." – Dave [52:09]

Best Bets (Mortals) and Full Cards

[53:45 – End]

• Each host goes through their full cards.

• Mortal Locks:

  • Rico: Oregon +3.5 as his immortal
  • Dave: Utah State +22.5
    • "Utah State is 3 and 1. One loss to A&M by 20... This game is good. We're not crowning Vandy a national champion quite yet. 22 points is a lot." – Dave [59:09]
  • Big Cat: Notre Dame-Arkansas over 64.5

• Moneyline Dogs:

  • Dave: Alabama vs. Georgia straight up (“My best moneyline is Alabama. I think they beat Georgia.”) [60:26]
  • Big Cat: Kentucky over South Carolina

Notable Quotes & Moments (with Timestamps)

• “I’m not 100% sure you bet it.” – Dave confronts Rico about his parlay, starting a segment that nearly brings Rico to tears. [06:24]
• "We're literally crying over spilled milk." – Big Cat, after the milk-puking/rash side tangent and mounting drama. [10:52]
• “You owe me at least a hundred grand. Figure it out.” – Dave to Jackie after the failed void on the Gruden parlay. [23:45]
• “You just took the hardest route to get there…” – Big Cat, mocking Rico’s betting process. [02:49]
• “If you have a daughter, you want her to date the star football player, not a wiggle dicker.” – Dave, on Lane Kiffin’s family’s media “distraction.” [41:07]
• “Franklin… 3-17 against the top ten, 1-14 against the top five… we don’t need the points, take them and shove them up your ass.” – Rico's full-throttle Duckies mortal promo. [48:08]
• “That little guy’s a real guy.” – Dave, defending Rico’s sandwich-sized win. [14:21]

Episode Tone & Style

True to Pick Em form, the hosts combine irreverence, relentless teasing, and real betting insight. The show’s tone is fast, combative, and self-effacing, with moments of office-family sincerity buried under layers of roast humor. Gambling talk is king, but almost equal time is given to the shenanigans and minor betrayals around the Barstool office.

Important Segment Summary & Timestamps

| Timestamp | Segment | Highlights | |-------------|-------------------------------------------|-------------------------------------------| | 01:29–06:16 | Opening banter, standings, slip drama | Rico’s near tears, “gotcha culture,” unit shaming blowup | | 16:06–24:42 | Octoberfest/Parlay controversy | Dave outs Jackie for missing $100K void | | 31:39–36:19 | Main game previews, Ryder Cup takes | Key picks debated; Dave’s indifference to Ryder Cup | | 36:40–52:53 | Remaining big games, hot takes | Oregon/PSU, Ole Miss/LSU, more, with rival fan ribbing | | 53:45–End | Full cards and mortal lock picks | Complete slate breakdown, mortals, moneylines |

Conclusion

This is a classic Barstool Pick Em where the football talk battles celebrity ego, gambling heartbreak, and the rituals that make the show so unfiltered and beloved. Whether you’re in it for betting analysis, backyard roast humor, or the inside scoop on Barstool’s wild culture, this episode delivers in spades.

LISTEN if you want:

• Relentless (and sometimes real) emotional breakdowns over bets
• Genuine college football insights hiding inside the chaos
• The inside drama—and inside jokes—of the Barstool Sports office
• A perfect “week in the life” of degenerate, deeply unserious gamblers