Should you use AI in fantasy football? Can it actually help you win games—maybe even a championship? Last year, I partnered with Greg Kellogg, a FSWA Hall of Famer, to test this in a head-to-head battle against AI. The only issue? We didn’t keep score. (Pro tip: humans forget, but algorithms don’t.) In 2025, we’re doing it right. We’ll be tracking results weekly, documenting everything, and sharing it with you. By the end of the season, you’ll have the answer to the question every fantasy manager is secretly asking: to AI, or not to AI?

Each week it’s me, Sir Whittington (Google AI’s fancy alter ego), and KROG squaring off. We’ll each be saddled with three random players — because let’s be honest, the biggest fantasy headaches usually come down to your flex spot.
Here’s how it works:
• One WR or RB ranked outside the top 24
• One TE ranked outside the top 12
• Our mission: pick the guy who can beat his projection and make us look smart.
Your mission: figure out if you should trust me, or the algorithm that also recommends you buy socks after shopping for lawn chairs.
Oh, and here’s the twist — the “winner” isn’t the one who scores the most points. Nope. Whoever’s players rack up the most points is actually the loser. We’re tallying it week by week to see who gets crowned by the end of the season.

This Week’s Players:

·       RB Jacory Croskey-Merritt (Bill)

·       WR Tetairoa McMillan

·       TE Kyle Pitts

We’re going in order: Sir Whittington → Krog → Tipp, to kick off the NFL’s first Sunday.

Aight, Sir Whittington — put down the tea and crumpets and give us your thoughts.

Sir Whittington’s Response:

1. Tetairoa McMillan

Arrived like the promising rookie hero, ready to claim his throne in Carolina’s WR pecking order. With hands like glue, a catch radius that could engulf small planets, and a knack for winning contested balls, McMillan looked like the answer to the Panthers’ “who’s the number one?” question. He was versatile, a red-zone threat, and had impressed enough in preseason to make managers drool. The catch? He wasn’t the fastest sprinter in the league, rookie nerves might hit, and Bryce Young’s arm could be more question mark than cannon. Still, in Week 1, he looked ready to make jaws drop.

2.Jacory Croskey-Merritt

A sleeper story, the underdog running back with explosive athleticism that made scouts whisper, “maybe, just maybe.” First-team reps in camp hinted at a starring role, and his inside-zone skills fit Washington’s playbook like a glove. But reality checked in: college stats were underwhelming, PPR upside was capped by Austin Ekeler on third downs, and goal-line glory might go to another. A timeshare loomed, meaning his touches could be more “slice of pie” than full feast. Still, if he got his shot, it could be magical.

3.Kyle Pitts

The tragic hero: a freakishly athletic tight end whose rookie season had been historic, but the years since had been… disappointing. Still only 24, Kyle Pitts had the potential for big plays and a deep-threat role in a new offense with Michael Penix Jr. at quarterback. Yet inconsistency haunted him, targets were scarce, and past glory didn’t guarantee Week 1 production. Managers hoped he’d break the spell and remind everyone why he was once a top-five pick.

And so, the three warriors prepared for their fantasy destinies: McMillan the rookie phenom, Croskey-Merritt the gamble, and Pitts the talent with a chip on his shoulder. Week 1 was coming, and only time would tell who would soar—and who would leave managers gnawing on their waiver-wire regrets.

Wow!  Having Jacory Croskey-Merritt as a flex option this week?  I don’t know Sir Whittington, ok let’s hear from our second AI friend.  Krog! You’re up! 

KROG’S Response:

1.Tetairoa McMillan

Strutted onto the field like the rookie messiah Carolina never knew it needed. Towering at 6’4”, he could snatch passes out of the sky like a vulture with a vendetta. His targets promised PPR points aplenty. But rookie jitters and Bryce Young’s inconsistent arm loomed like storm clouds. Will he soar or faceplant spectacularly? Only fate—and the Jaguars’ shaky secondary—would tell.

2. Kyle Pitts

Wandered in next, a prodigy turned cautionary tale. Once a rookie sensation, now a talented tight end haunted by inconsistent production and split snaps. A new OC and Michael Penix Jr. arm might resurrect him from fantasy purgatory, but every pass came with a whisper: “remember 2024?” Injuries, target competition, and limited red-zone love made Pitts a high-risk gamble, the kind you’d roll for if you enjoy living on the edge of heartbreak.

3. Jacory Croskey-Merritt

Slunk onto the scene like the underdog with a glittering highlight reel but a résumé full of question marks. He might get the lead back role in Washington, or he might disappear into a timeshare abyss. If he succeeds, it’ll be a glorious surprise. If not… well, fantasy managers might mourn quietly at their waiver wire.

And so, the rankings were decreed: McMillan for consistent (hopeful) glory, Pitts for risky talent with redemption potential, and Croskey-Merritt for the gamble that could haunt or delight. Week 1 awaited, a cruel reminder that in fantasy football, hope and despair are separated by the thinnest of lines—and sometimes a dropped pass.


Tipp’s Response:

1.Tetairoa McMillan  

Alright, this is going to be fun duking it out with these two though I’m rolling with Tetairoa McMillan too — so it’s a clean sweep for Sir Whittington, KROG, and me.  Here’s why: Carolina opens against Jacksonville, and last year the Jags gave up the second-most fantasy points to wide receivers. Sure, they’ve invested in the secondary, but cohesion doesn’t happen overnight. Week 1 could still be leaky.  Speaking of cohesion… have you seen the chemistry between Bryce Young and McMillan? That connection looks like it was downloaded straight from Madden.

2. Kyle Pitts

Yes, Kyle Pitts is a freak. Yes, he’s on an offense that should be good (projected points don’t win games, but hey, we’re optimists here). What’s more important is that both the OC and Michael Penix Jr. have been hyping him up all offseason, calling him a focal point and a matchup nightmare. Now, Pitts won’t leapfrog Bijan Robinson or Drake London in the pecking order, but with Darnell Mooney nursing a shoulder injury, he’s got a clear path to extra targets in Week 1. And with the Falcons opening against a division rival in Tampa, Penix is going to have to sling it. Translation: Pitts has a real chance to make fantasy managers forget about his past frustrations — at least for one week.

3. Jacory Croskey-Merritt

I’m more in line with KROG’s rankings here, but let’s talk about Sir Whittington. On what planet does Croskey-Merritt crack the top 25? Ya I’ll be sleeping on Croskey-Merritt in Week 1.  Not happening! Yes, the Giants gave up a ton of yards to running backs last season — but that defense is healthier now and added reinforcements. The real red flag? Washington is carrying four running backs who could all see touches. That’s not a backfield, that’s a timeshare nightmare. And hopefully you didn’t overreact to that preseason game against the Bengals’ JV defense and burn an 8th-round pick, because the usage won’t be that pretty in Week 1. Plus, Croskey-Merritt’s pass protection is a concern. If you can’t keep Jayden Daniels upright, you’re not seeing the field much. Will Croskey-Merritt make an impact? Probably. But it might not be until later in the season — patience required.

Week 1 Breakdown:

Sir Whittington

1.   Tetiaroa McMillian

2.   Jacory Croskey-Merritt

3.   Kyle Pitts

KROG

1.   Tetiaroa McMillian

2.   Kyle Pitts

3.   Jacory Croskey-Merritt

Tipp

1.   Tetiaroa McMillian

2.   Kyle Pitts

3.   Jacory Croskey-Merritt