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

Welcome back to Sharper Square. I’m here with my partner in crime, Simon Hunter, and I’m still buzzing from our chat about algorithmic betting—tech is flying, prediction markets are cranking, and AI is changing how fast edges appear and disappear.

If you bet for a living, you’ve got to learn this stuff. I took an AI modeling course, and it widened my lens; edges exist, but books catch up faster now, so advantages feel seasonal, not multi‑year.

If every pro uses AI, is it really an edge, or just speed?

It’s still an edge if your use is novel. Pros won’t broadcast their methods, and LLMs can chew through trend work in seconds; you’ll hear the old tricks in a couple years, which will still spark new ideas.

I live in Claude. From dinner timing to manuscript notes, I pay for the fastest version because I want instant, thoughtful output across everything.

Project that a decade out and it’s wild; we’re already seeing awkward uses like pasted dating prompts—authenticity’s taking a hit.

All right, mailbag time with Matt Mitchell. Quick one first—what AI prompts are people accidentally sending you, Simon?

She once replied with the model’s list of a town’s highlights instead of her own; buddies even run questions past AI before they ask their spouses. It’s a weird moment.

Friends of mine use LLMs to rehearse negotiations and scan contracts, and they catch clauses lawyers miss. No one listening needs a lecture—these tools are already table stakes.

Spring Mailbag Day. First up: why would the Dolphins hand Devon Achane a huge deal while tearing it down under a new regime?

It’s classic Miami chaos. He’s electric, but paying a running back like a cornerstone during a reset ignores positional value; you build lines, QB, and receivers first, then splurge at RB.

And Malik Willis to Miami on a short deal—how does that fit a rebuild?

He’s a bridge. If he pops, great; if not, they draft a quarterback next spring and move on.

Next: John Harbaugh to the Giants. Over or under their seven‑and‑a‑half, and what happens to the front office?

I’m under. I don’t think Jackson Dart or Cam Skatteboo lasts the whole year, and I’d expect Joe Schoen out before the next draft as they reset again in a deep QB class.

Even if Dart flashes, that division’s brutal. Best case, he becomes a durable Pro Bowler; worst case, they stay stuck near the bottom while the franchise searches for direction.

I don’t get the blind optimism. In Baltimore, coordinator choices and postseason management kept capping them, and he’s importing the same crew to New York.

On to Pittsburgh after Tomlin, with Cowherd roasting the Rodgers saga: are the Steelers headed for a real dip or more middle‑of‑the‑road finishes?

Tomlin’s voodoo masked roster issues for years. Without him, the aging defense and QB limbo should bite; I’m leaning under while the Rodgers drama drags.

Since the sixties, the Steelers thrived by hiring young, long‑view coaches. Mike McCarthy is a short‑term retread and feels misaligned with that identity.

Speed round: with Kyler Murray now in Minnesota, what happens to JJ McCarthy?

Kyler’s the favorite unless JJ detonates in camp; Kyler’s seen more, still the superior athlete, and that scheme can elevate him.

If Kevin O’Connell reshapes Kyler’s approach the way he’s boosted past QBs, that offense can get scary fast.

What are you each genuinely afraid of?

Small to medium dead animals. The weight on a shovel and the ‘spirit’ of it grosses me out every time.

Commitment, and sleep‑paralysis spiders that feel huge and inescapable.

Thanksgiving games: love or hate?

Hate when the Bears kick off early; I want the build‑up and primetime energy.

I love it, especially Dallas on the slate, though a loss can wreck dinner.

Quick pet detour: Simon, your house‑sized cat?

Indigo’s a massive Maine Coon who needs a kid’s sandbox for litter and treats my studio like an obstacle course.

Team you’d least want to root for right now?

The Giants—unclear plan and a muddy path. I prefer hard resets like Arizona or Miami.

The Bengals over the Jets by a hair: questionable ownership habits, aging core, and a star QB who can’t stay upright.

I’ll say Jets; even re‑signing Geno cracked me up while they still angle for Rodgers.

Final one: after Indiana’s shock national title, what would top it for sheer disbelief?

Official confirmation that extraterrestrials are here now.

Humans settling Mars in our lifetime—I’d buy a one‑way ticket.

I’ll interview the lizard people on their Mars porch before I count on a Bills parade.

We go to Mars because it’s there. Thanks for the questions—next week we’re diving into the schedule and week one lines. Love you all.