Nightcap – "Deebo & Joe – Part 2: NFL Free Agency Winners & Losers"

March 13, 2026 | iHeartPodcasts & Shay Shay Media
Hosts: Deebo & Joe

Episode Overview

This episode of Nightcap dives deep into the NFL’s free agency period, with Deebo and Joe breaking down the league’s biggest winners and losers, sharing insights on specific team moves, contracts, and trends. The conversation is characteristically unfiltered and humorous, featuring sharp banter, real talk about front office strategies, discussion on NCAA NIL issues, and lively engagement with fan questions. Expect passionate Steelers and Browns takes, a candid debate about the evolving landscape for NFL and college players, and memorable locker room storytelling.

Key Discussions & Insights

1. Debate on “Winners and Losers” Lists

• [03:56–05:12]
  • Deebo introduces USA Today's list of free agency winners and losers.
  • Joe questions why Max Crosby is listed as a "loser," noting:
    “The Baltimore Ravens GM I say he lost.” (04:21)
  • Deebo challenges that:
    “You got to see whose perspective that you’re looking from… did he lose business-wise?” (04:32)
  • “They don’t care about your feelings,” Deebo emphasizes, referring to the cold business calculations of NFL offices. (04:45)

2. Cleveland Browns’ Free Agency Moves

• [05:21–07:58]
  • Joe passionately highlights Browns line signings:
    “We did our thing... our line is backstack. We’re protecting Shador.” (06:00)
  • Details on new additions: Titus Howard, Jenkins, Zion Johnson, and depth plans.
  • Deebo pokes fun at contract lengths and future depth:
    “So in two years, you go lose all your linemen but one.” (07:10)
  • Joe’s retort:
    “No, no, no, no. Don’t want to hear none of that…Andrew Barry out here doing what he’s supposed to do.” (07:22)

3. Steelers’ Aggressive Offseason

• [08:17–11:42]
  • Both hosts agree Steelers GM Omar Khan is “cooking”:
    “They let that man go… They don’t unsnap the leash.” (08:58, Deebo)
  • Moves praised:
    • Signing of Rico Dowdle (RB).
    • Strong deals for Deane and bringing in Pittman Jr.
    • Focus on physical skill-position players:
      “Our tight end is 311 pounds.” (10:50, Joe)
  • Deebo’s vision:
    “Well, we’re gonna be lined up by three wide, and we gonna run that ball down your mother throw.” (11:12)

4. Defining the Biggest Winner in Free Agency

• [13:14–15:40]
  • Joe’s Winner: “Steelers, biggest winner.” (13:23)
  • Deebo:
    “It’s gonna sound crazy... they got 99 million reasons they’re the biggest winner. Oh, Tua Tagovailoa... That man ain’t got to go to work.” (14:46)
  • Joe agrees, marveling at guaranteed contracts:
    “He hit a hundred million to chill.” (15:33)

5. The Value of Reputation When You’re Paid

• [16:31–17:16]
  • Deebo ponders if he’d care about being called a bust with $99 million:
    “Would I care if I was considered a bust with 99 sitting in my pocket?” (16:31)
  • Joe:
    “You had 160. Tuck away, be gone. Chilling.” (17:05)

6. NCAA, NIL, & The Future of College Football

• [22:49–31:16]
  • Discussion of Trinidad Chambers’ eligibility battle and lost NIL/EA Sports deal:
    “So this is huge because… potential millions lost… NLI income.” (25:13, Deebo)
  • Breakdown of the House v. NCAA settlement and revenue sharing:
    “If that House vs NCAA settlement is approved, it could change everything… players would be getting a percentage of the revenue.” (26:26, Deebo)
    • SEC and Big Ten would dominate due to outsized TV revenue.
    • Concerns about cap limits, equity among sports.
  • Joe and Deebo remember playing “guarantee games” for HBCUs:
    “We got paid to go get our face kicked in two, three times a year at somebody’s homecoming.” (31:04, Deebo)

7. Interactive Segment: “Player or Fade”

• [31:30–34:58]
  • Joe and Deebo set lines for NBA prospects and debate fantasy picks, favoring safe bets for steady winnings:
    “Just know it might not be the craziest, but you’re not going, we’re not gonna lose.” (33:45, Joe)

8. Super Chat & Fan Engagement

• [34:58–54:43]
  • Fun “airport photo” story:
    “If I’m in a rush trying to get to a flight… No sir, I gotta go.” (47:01, Deebo)
  • Draft prospects:
    “Which receiver in the draft would be hardest to contain?” (49:04)
    • Joe: “Tate…Ohio State…He got a little bit of everything.” (49:04)
  • Defensive memories—hilarious tales of teammates, collisions, and the art of the big hit.

9. Quick Takes: Browns, Quarterbacks, and AFC North

• [44:46–46:16]
  • Joe bullish on Browns' outlook, predicts a Cleveland–Pittsburgh showdown:
    “It’s gonna be between us, the Browns and the Steelers.” (45:11)
  • Dismissal of Baltimore’s prospects post-free agency:
    “They don’t have their center anymore.” (45:23)

10. Minkah Fitzpatrick’s Move & Respect for Ballers

• [52:49–54:09]
  • Joe argues Minka is undervalued, lauds his game intelligence:
    “He’s best safety. One of the best safety I played with. He’s locked in.” (53:02)

11. Personal Notes & Closing Thoughts

• [54:40–55:47]
  • Deebo shares a candid moment about fighting “the devil” and relying on faith to get through tough times: “I got to a fight with the devil… had me punch drunk… you can’t fight it with nothing else but the word.” (54:42–55:47)

Notable Quotes

• Deebo on business over feelings in the NFL:
  “They don’t care about your feelings.” (04:45)
• Joe on Browns free agency:
  “Our line is backstack. We’re protecting Shador.” (06:00)
• Deebo on Steelers’ GM Omar Khan:
  “They don’t unsnap the leash. I said watching.” (08:58)
• Deebo on cashing out as a “bust”:
  “Would I care if I was considered a bust with 99 sitting in my pocket?” (16:31)
• Joe on Minkah Fitzpatrick:
  “He’s locked in. He studies his tape. He knows what’s going on.” (53:02)
• Deebo on perseverance:
  “The word too strong. He’s fighting with this word.” (55:34)

Memorable Moments

• Deebo’s playful antagonism about Browns’ future O-line depth, refusing to let Joe’s optimism stand unchecked. (07:12)
• A focused, funny breakdown of fan’s “put a running back at QB” question, which Joe initially takes as a dig at Cleveland and Lamar Jackson. (43:03–44:39)
• Reminiscing about the harsh business of college “guarantee games” for underdog teams. (31:04)
• A running joke about the pain and confusion of getting hit by your own teammate while making a tackle. (49:51–51:53)

Timestamps for Key Segments

• Introduces “Winners & Losers” List: 03:56
• Browns Free Agency Discussion: 05:21–07:58
• Steelers & Omar Khan Praise: 08:17–11:42
• Biggest Winner Debate (Steelers & Tua): 13:14–15:40
• NCAA/NIL Discussion: 22:49–31:16
• Player or Fade Segment (NBA props): 31:30–34:58
• Fan Q&A, Stories & AFC North Predictions: 44:46–46:16
• Minka Fitzpatrick Segment: 52:49–54:09
• Deebo’s “fight with the devil”: 54:40–55:47

Tone & Style

The episode is lively, unscripted, and filled with authentic locker-room style banter. Both Deebo and Joe blend sharp football insight with humor, humility, and a touch of motivational real talk, maintaining accessibility for hardcore and casual fans alike.

For listeners seeking an honest, funny, and insightful breakdown of 2026 NFL free agency moves—and how the business of football keeps reshaping both the pros and the college game—this Nightcap episode delivers.