Barstool Pick Em | E221: Rico Bosco Negotiates His Contract With Dave Portnoy | Bowl Preview (Dec 19, 2025)

Episode Overview

This episode of Barstool Pick Em features Big Cat (Dan Katz), Dave Portnoy (Pres), and Rico Bosco as they dissect college football bowl season and, more importantly, dive into an extended, comically transparent negotiation between Rico and Dave about Rico’s contract. True to form, the hosts roast each other, bust balls, and weave Barstool office drama and their trademark gambling pessimism into their unique brand of college football “analysis.”

Key Discussion Points and Insights

1. Holiday Party Debrief & Office Shenanigans

• The crew opens with recaps of the Barstool holiday party, focusing on viral videos of Rico “mean-mugging” coworkers and minor intra-office beefs. Light ribbing sets the tone for the more serious—well, Barstool serious—discussions that follow.
  • [03:01] Dave: “I saw a video of you just mean mugging Meek Phil...looked like you pooped your pants in the background.”
  • [03:35] Rico: “It was a great party. It's good to say hello to everybody. It's been a great year.”

2. Michigan Football Chaos & Leadership Drama

• Dave dives into the ongoing chaos at Michigan surrounding the football program’s leadership, with asides about regents infighting, who’s really in charge, and the potential candidates to stabilize the team. This becomes a major segment and classic “Pres rants” moment.
  • [07:40] Dave: “Every day that goes by, I don't see how these kids are going to stay there. We have major problems. And I just. I don't know how you start when you don't even know who's running the show.”
  • He proposes outlandish solutions (“make Larry Ellison the czar of Michigan football”) and openly fantasizes about hiring a coach himself.
  • [09:47] Dave: “At one point, I thought I was getting on a plane to fly to Ann Arbor…that was total garbage.”

3. Barstool Office Dynamics & Old Sins

• The hosts reflect on office history, negotiating pointers, and personal accountability. Rico pokes fun at his past mistakes, referencing old drug-fueled days and learning to “laugh at yourself.”
  • [05:23] Rico: “Listen, you are a victim of your old sins. You can only get better.”

4. The Rico Contract Negotiation: Farce and Foresight

a) The Negotiation Ritual

• Rico’s expiring contract becomes the centerpiece, with the hosts lampooning the entire process.
• Rico insists he’ll stick to “the plan,” but Dan and Dave badger him for negotiation details; the conversation quickly devolves into comic banter and role play.
  • [21:56] Dave: “My biggest problem before I can get to that [contract] is I gotta figure out how to look at spreadsheets if we're being honest.”
  • [29:01] Rico: “That's what you're gonna say? What are you thinking?”
  • [29:06] Dan: “What are you thinking? Percentage. No, don't say numbers.”
• Hilarious admissions come out, including a past incident where Rico was accidentally (or not?) overpaid and didn't say a word about it.
  • [26:57] Dave: “We overpaid Bosco too much money. He knew it. Never said thank you, and then acted like I knew he was getting paid too much.”

b) The Monologue & Bosco's “Intangibles”

• Hank requests Rico’s negotiation “monologue,” and Rico delivers a comically earnest, sports-coach-style pitch heavy on “intangibles.”
  • [31:37] Rico: “Intangibles. Yeah. Diving for loose balls, hot assists, clapping on the bench.”
  • The crew jokes about how much Rico should be paid for his off-the-scoreboard value (“Do NBA players get paid more for clapping on the bench?” [31:54])

c) Rico’s Million-Dollar Dream (Confusion Ensues)

• Rico states a long-term goal—to "bring in a million dollars" for the company—creating a spiral of confusion as Dave and Dan try to figure out if Rico is aiming for a $1M salary or $1M in ad revenue.
  • [40:01] Rico: “I have a goal. I want to earn a million dollars in 2026. That's where I'm at.”
  • [41:55] Dave: “Are you saying you want your W2 to be like a million dollars? That's what I'm asking.”
  • [43:03] Rico: (after much confusion) “No, I would like to bring in a million dollars. That's a great start there.”

d) Candid Feedback: Is Rico a “Leading Man”?

• Dave gives honest (brutal) appraisals of Rico’s role: epic as a member of the Pick ‘Em trio, less compelling as a solo or “leading man.”
  • [61:16] Dave: “When you're with me getting your buttons pushed, I can't turn away. When you're the leading man, I fall asleep. I don't know how to fix though.”
• Dan and Hank chime in to soften the blow, contextualizing that the best content often comes from “office interplay” and ensemble, not solo acts.

e) New Content Ideas

• Rico pitches series concepts: “Doc-style” vignettes on heated high school or small-town rivalries, and visiting obsessive superfans at home.
  • Both ideas are lauded for enthusiasm, but the crew reminds Rico that these are harder and more expensive than they sound, and that Roan already did the superfan concept.
  • [53:24] Dan: “Roan did it. I remember the Buffalo Bills guys…”
  • [54:45] Dave: “Documentaries cost. Can you do it man on the street style, maybe. But it's really, really hard.”

Notable Quotes & Memorable Moments (with Timestamps)

• [13:54] Dave: “Get somebody who everyone agrees is like, morally in the right spot but I don't know how. They're just doing nothing.”
• [16:02] Dan: “You'd be like, yeah, that's a great deal because we won a national title.”
• [29:06] Dan: “What are you thinking? Percentage. No, don’t say numbers.”
• [31:37] Rico: “Intangibles. Yeah. Diving for loose balls, hot assists, clapping on the bench.”
• [40:01] Rico: “I have a goal. I want to earn a million dollars in 2026. That’s where I’m at. So day by day, stick with the plan.”
• [61:16] Dave: “When you’re with me getting your buttons pushed, I can’t turn away. When you’re the leading man, I fall asleep.”
• [66:08] Hank: “But being a nine hitter on a World Series contending team…”
• [68:51] Dave: “It was the biggest no brainer deal that I’ve seen cross our desk. To me it was the easiest decision to make.”
• [72:24] Dave: “We’ve been trying to get deals and partners. That’s how you grow.”

Timestamped Segment Guide

• [00:00–02:38] Ads, show intro, holiday greetings, office banter
• [02:42–04:56] Holiday party recap; Rico’s party demeanor, data team jokes
• [05:07–14:44] Michigan football chaos, leadership drama, Portnoy rants
• [15:54–19:54] The “Michigan Man” ideal and recent program scandals
• [21:56–26:26] Spreadsheet complaints & contract negotiation tease
• [26:27–32:27] The negotiation dance, past overpayment, “intangibles”
• [32:37–44:01] Rico’s negotiation monologue, his million-dollar aspirations
• [54:45–58:52] Content ideas/feedback, recurring challenges with Barstool video docs
• [61:16–66:31] “Leading man” debate; office dynamic vs. solo work
• [67:52–72:47] Netflix deal talk; Barstool’s platform moves
• [73:17–86:07] Misc: gift gags, bowl game picks, “clarification” digressions, more ballbusting
• [86:08–end] Final thoughts, picks, sign-off banter

Tone & Flow

The episode is classic Barstool Pick Em—chaotic, irreverent, deeply self-referential, and more preoccupied with internal banter than actual sports handicapping. Office politics and relationships are foregrounded, with a running undercurrent about the absurdity and genuine affection within Barstool. The humor oscillates from deadpan to slapstick, with no sacred cows (especially not Rico).

Takeaways for New Listeners

• The bulk of the episode is a parody-tinged, semi-serious negotiation, painting an honest picture of Barstool’s internal logic (and illogic).
• Dave’s leadership rants and unfiltered feedback demonstrate Barstool’s “sink or swim” culture and why on-air chemistry trumps analytics.
• Every contract negotiation, spreadsheet, or pitch is a content opportunity—no inside baseball is too granular for the show.
• Coverage of the actual bowl games is present but secondary, consumed by the office dynamic, and often played for laughs over analysis.

Recommended Listening Points

• [27:06] for the story about accidental overpayment
• [29:01–32:27] for classic barstool negotiation banter
• [40:01–43:10] for the million-dollar monologue and confusion
• [61:16–63:11] for the “leading man” feedback and team roles in content
• [68:51–72:47] for Netflix deal behind-the-scenes insight
• [83:36–85:33] for rapid-fire bowl picks and mortal locks

This episode is a must-listen for fans invested in Barstool behind-the-scenes, the office soap opera, and the real human comedy that runs beneath the gambling pretense. Football picks happen, but the main event is a live, unscripted look at what makes Barstool...Barstool.