Sharp or Square - NFL MAILBAG - De'Von Achane Contract, NFL Schedule and More

The Herd with Colin Cowherd48mMay 14, 2026

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AI-Generated Summary

In this episode of Sharper Square, hosts Chad Millman and Simon Hunter tackle a fan mailbag centered on NFL offseason developments, including the Miami Dolphins' decision to give running back De'Von Achane a massive four-year, $64 million extension despite the team's ongoing rebuild. The hosts critique Miami's organizational priorities, arguing that investing heavily in a running back while neglecting quarterback and offensive line development is short-sighted, especially given their likely draft position. They also analyze the New York Giants' hiring of John Harbaugh and their signing of Malik Willis, questioning the long-term vision of a franchise that appears directionless. The discussion turns to the Pittsburgh Steelers' post-Mike Tomlin era under Mike McCarthy, with the hosts expressing skepticism about his ability to revitalize a team lacking quarterback stability and draft success. The episode also features a lighthearted 'griefer speed round' where the hosts share personal fears, including dead animals and sleep paralysis, and debate which NFL franchises would be the worst to support. The show closes with a speculative discussion on future milestones, from extraterrestrial life to human settlement on Mars.

Key Takeaways
1

Miami Dolphins' $64M extension for De'Von Achane is a misstep given their rebuild priorities and lack of quarterback development.

2

The New York Giants' hiring of John Harbaugh and signing of Malik Willis signals a lack of long-term quarterback strategy.

3

Pittsburgh Steelers' post-Tomlin era under Mike McCarthy is viewed as a mismatch with the franchise's historical coaching philosophy.

4

AI tools like Claude are becoming essential for professional bettors, but their widespread use may erode long-term competitive edges.

5

The NFL's Thanksgiving scheduling often disadvantages fans whose teams play early games, disrupting the holiday experience.

Chapters
0:00
2 min

Intro and Sponsor Segments

The episode opens with multiple iHeartRadio sponsor promos for podcasts like Humor Me, Radio 831, Superhuman, Hurdle, and Sports Slice, followed by the introduction of Sharper Square with hosts Chad Millman and Simon Hunter.

2:00
6 min

AI in Sports Betting: The New Edge

If everyone has access to AI, it doesn't necessarily mean you get an edge. It just means you're doing it faster and more efficiently.

Highlight
8:00
9 min

Miami Dolphins' De'Von Achane Contract Critique

You want to build the offensive line, the defensive line, get the quarterback, get receivers. Then you can go get the running back and pay them.

Highlight
17:00
10 min

Giants' John Harbaugh Hire and QB Strategy

They're not doing that at all. He's just a stopgap quarterback.

Highlight
27:00
13 min

Pittsburgh Steelers' Post-Tomlin Era

The hosts analyze the Steelers' transition after Mike Tomlin's departure, criticizing Mike McCarthy's hiring as a mismatch with Pittsburgh's tradition of long-term, culturally aligned coaches. They predict continued mediocrity unless major changes occur.

High-Impact Quotes
I'm going to be one of those people. I will buy that one-way ticket and I will happily die on Mars just because that's the ultimate experience.
Simon Hunter54:58
Viral: 95.0
I would say to truly blow my mind that I could never see coming would just be people living on Mars.
Simon Hunter54:18
Viral: 90.0
The issue is this Mike, Mike, Mike, Mike, Mike Tomlin... Mike McCarthy's a 60 something year old reach rat.
Simon Hunter31:22
Viral: 85.0
Speakers

Hosts

Chad MillmanSimon Hunter

Guest

Matt Mitchell
Topics Discussed
NFL Team Rebuilds90%AI in Sports Betting85%Quarterback Development80%NFL Coaching Hires75%Sports Franchise Management70%Fan Experience and Scheduling65%Future of Human Exploration60%Personal Fears and Quirks55%
People & Brands

Simon Hunter

person

25xNeutral

Chad Millman

person

24xNeutral

Claude

other

12xPositive

Miami Dolphins

other

12xNegative

Pittsburgh Steelers

other

10xNegative

New York Giants

other

10xNegative

De'Von Achane

person

8xNeutral

Matt Mitchell

person

8xNeutral

Mike McCarthy

person

7xNegative

John Harbaugh

person

6xNegative

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