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Should You Use AI (Artificial Intelligence) in Fantasy Football?

Can it actually help you win games — maybe even a championship? Last year, I partnered with Greg Kellogg, an FSWA Hall of Famer, to put it to the test in a head-to-head battle against AI. The only problem: we didn’t track the results. (Lesson learned — humans forget, 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 finally have the answer to the question every fantasy manager quietly asks themselves: To AI, or Not To AI? Each week, I’ll be joined by Sir Whittington (Google AI’s alter ego) and KROG. We’ll each be assigned three random players — because the biggest fantasy headaches almost always come down to your flex spot. 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: decide whether to trust me, or the algorithm that also recommends socks after you shop for lawn chairs And here’s the twist — the “winner” each week is not the player who scores the most points. The highest score is actually the losing outcome. Lowest season-long score wins the title. Speaking of title if you are in your fantasy playoff congrats. Here are the results from Week 14.

Week 14 Results:

RB Kyle Monangai- 8.7 points

WR Alec Pierce- 13 points

Kyle Pitts- 15 points

For our yearly result of Man vs. Machine

Sir Whittington-34 points

KROG-48 points

Tipp- 34 points

After a short lead I find myself tied with Sir Whittington yet again. KROG, well he tired. For Week 15 lets start with Sir Whittington.

Sir Whitttington Response:

At this stage of the fantasy season, confidence is a luxury few managers can afford. Every lineup decision feels like a referendum on your intelligence, and optimism has long since been replaced by quiet hope and emotional hedging. With that in mind, let’s assess three options who offer varying degrees of safety, risk, and sheer audacity.

George Kittle remains one of fantasy football’s few remaining comforts. While chaos reigns across most tight end rooms, Kittle continues to operate as a dependable focal point in a high-powered San Francisco offense. His target share is steady, his red-zone involvement is secure, and his weekly production rarely descends into farce. The matchup with Tennessee is particularly agreeable. The Titans have struggled to contain tight ends, and Kittle’s role ensures both a respectable floor and the ever-present chance of a ceiling game. He may not always dominate the box score, but he almost never sabotages your week. Bottom line: The safest play of the group by a considerable margin. Start Kittle with confidence and use the saved mental energy elsewhere perhaps on your inevitably more complicated flex decision.

Jordan Mason is the sort of fantasy option you select after sighing and saying, “Well, he could score.” His production profile is straightforward: efficient runner, red-zone usage when given the chance, and very little involvement as a receiver. Unfortunately, that simplicity is also his limitation. Mason remains stuck in a committee, and without meaningful passing-game work, his PPR value relies heavily on touchdowns. When he finds the end zone, he looks like a shrewd play. When he doesn’t, he offers very little consolation. Bottom line: A reasonable but uninspiring flex. Mason is acceptable if you’re thin at running back, but starting him requires accepting that your fate may be decided by a goal-line carry or two.

Kayshon Boutte is fantasy football at its most reckless. His high average depth of target and explosive skill set mean he is always capable of flipping a matchup with one catch. On paper, that makes him intriguing. In reality, it makes him deeply stressful. His weekly usage is wildly inconsistent, the Patriots’ passing game is unreliable, and the matchup does him no favours. Boutte is the sort of player who can deliver 60 yards and a touchdown—or finish with one target and leave you staring blankly at your lineup. Bottom line: A full boom-or-bust dart throw. Only start Boutte if you’re chasing upside and have already made peace with the possibility of disaster.

KROG’S Response:

Fantasy football can be unpredictable. One week, your stud TE hauls in everything in sight. The next, your WR disappears like socks in the dryer. Let’s break down three players you’re thinking about starting this week—with some humor to keep your sanity.

George Kittle is basically the dependable friend who always shows up to parties… and brings the snacks. He’s running routes like it’s cardio season (87% route rate!) and soaking up targets like a sponge (22% target share). The Titans’ defense against TEs isn’t exactly daunting, which means Kittle could rack up catches, yards, and—if the 49ers get close to the end zone some touchdowns too. Bottom line: Safe floor, high ceiling, and basically a must-start. Your TE nightmares are over… unless he drops a pass, but let’s not go there.

Kayshon Boutte is the fantasy equivalent of a rollercoaster: thrilling, slightly terrifying, and likely to make you scream at 3 a.m. in your dreams. He can go deep and hit a massive play thanks to his chemistry with Drake Maye, but let’s not forget the Bills’ secondary is lurking like a grumpy cat ready to swat. Low weekly target floor means he could also… just sit there like a benchwarmer. Bottom line: Boom-bust flex option. If he hits, he hits big. If he doesn’t… well, at least you’ll have a story about the one that got away.

Jordan Mason’s situation is like sharing a slice of pizza with three friends you might get a bite, you might get crumbs. He runs efficiently and can score near the goal line, but he’s not much of a receiving threat in PPR leagues. If Aaron Jones gets hurt, Mason could shine. Otherwise, expect inconsistent touches that make your lineup anxiety spike. Bottom line: Low-end flex with touchdown upside. Only start if you like living on the edge or if you really, really like Minnesota pizza metaphors.

Tipp’ s Response:

Fantasy football is all about matchups, opportunity, and a tiny bit of luck. Here’s a look at three players you might be considering this week as a flex option.

George Kittle has a favorable matchup against Tennessee. The last two tight ends to face the Titans found the end zone, and while the 49ers don’t necessarily need Kittle to carry the passing game, his talent is too good to ignore. He’s reliable, can deliver catches, and has red-zone upside—even in a balanced 49ers attack. Bottom line: Reliable TE1 with red-zone upside. Start with confidence low-risk, high-reward.

Jordan Mason faces a Cowboys defense that has tightened up against the run recently. Still, the Vikings may lean on the rushing attack to control the game and avoid a shootout. Last week, they ran the ball 34 times, and it’s unlikely J.J. McCarthy will be in a pass-heavy game plan this week. Mason could see enough touches to offer PPR value, especially near the goal line. Bottom line: Low-end flex with touchdown upside. Best for managers who need a steady option in a potentially run-heavy game script.

Kayshon Boutte has been a pleasant surprise this season but remains boom-or-bust. Unfortunately, this week’s divisional matchup against the Bills could be one of those “quiet” weeks. Both teams like to run the ball, and while some have predicted a shootout, this game looks more like a grinder. By the fourth quarter, Boutte could have just one target, quietly forgotten in the offense. Bottom line: Risky WR3/flex. Likely low target volume best left on the bench unless you need a home-run play.

Week 15 Breakdown:

Sir Whittington

  1. TE George Kittle
  2. Jordan Mason
  3. Kayshon Boutte

KROG

  1. George Kittle
  2. Kayshon Boutte
  3. Jordan Mason

Tipp

  1. George Kittle
  2. Jordan Mason
  3. Kayshon Boutte