I Fired Myself From Fantasy Football. Claude Took the Job.
VictoriousSecret has been my fantasy football name for over a decade now. I used to enjoy it a lot more than I do now - draft nights at the cigar bar, and data wasn’t something I did all day every day.
A warm, slightly humorous editorial illustration split in two moods. Left: a dim cigar bar on fantasy draft night, five friends around a leather booth with paper draft boards, highlighters and drinks, golden lamplight, nostalgic. Right: the same table years later, one tired man in a hoodie with a laptop full of options charts and spreadsheets while a friendly, slightly smug robot with a clipboard quietly sets his fantasy lineup. Painterly, warm color palette, subtle film grain, wide 16:9, no text, no logos, no NFL or team marks, no real people.
I spend all day selling options and staring at numbers. Then Sunday comes around and apparently I'm supposed to enjoy staring at different numbers.
I still like football. Fantasy football started feeling like more work, and I already have plenty of that. By the weekend I don't care who got how many targets. I want to sit down and watch the damn game.
So this year I turned my waivers, my FAAB, my trading, all over Claude. Built a full dossier on everyone.
Checked out
My league is on Sleeper. Twelve teams, superflex dynasty (keep your guys forever, start two QBs), five seasons in. I won in 2023. $1500 to the winner in this league, so by winning in year two and a $200 annual buy-in, it bought me 7 years of playing for free. My buddy Mikey won the first year, 2022. Keep him in mind because we're going to pick on him in a minute. He’s also one of my few personal friends who I’ve let know I even write this here blog and should get a kick out of reading.
My internet went out during the 2025 rookie draft. Couldn't get word to anybody, draft kept going, and I got hosed. I was pissed as hell and pretty much checked out for the season. Very mature of me, I know. Kinda like losing a bunch of money trading futures is a great way to teach someone else a lesson. Enter eye roll here.
How checked out? Six waiver claims in fourteen weeks. Spent $20 of my $250 waiver budget. Finished 4-10.
This summer I finally looked at the mess. Six players over the roster limit. No defense, even though we have to start one. Everybody else was using their taxi squad (the rookie stash) and mine was empty. I asked Claude to help because clearly I wasn't doing it.
One button
The thing runs on Python and sends me a card in Discord when it wants to make a move. I get two buttons, "Do it" and "Nah." Trades and roster moves wait for me to press one. I can manage that much.
I did let it handle lineups without me. It checks before the Thursday game, Sunday morning, the 1pm and 4pm games, Sunday night and Monday night. Thursday's check is an hour before kickoff, after inactives come out. Leaving an empty slot gets you zero. There isn't much of a decision there.
First day it cut seven players, put rookies on the taxi squad, and submitted a waiver claim for a defense. Then it decided we should start trading.
The receipts
I asked Claude if there was enough here for an article. It went back through five seasons of our league and pulled this out.
One of the numbers was lineup efficiency. Points you actually scored divided by the most you could have scored with the players you already owned. Basically, how much did you screw up picking starters?
Mine was 80.7% in 2025. Last place. I left 417 points on the bench over fourteen weeks. 417 / 14 = 29.8 points a week. Almost thirty! With the best possible starters each week, my 4-10 would have been 8-6. I had players. I wasn't paying attention. Was too poor to pay attention. Dad joke knee slapper!
Through four weeks this year, with Claude picking the lineup, I'm at 90.4%. First in the league. And I'm 2-2.
The perfect-lineup version is 4-0. Weeks two and three had points on the bench that would have won, and we found a stupid bug: the agent was updating my roster's default starters. Sleeper uses a separate lineup for each week. It kept getting a success response, so it thought it had done the job. It hadn't changed the lineup being scored. Fixed that October 4. Now it reads the weekly lineup back to check.
I hired a robot to avoid screwing this up and it promptly screwed this up.
Nobody has accepted a trade yet, either. Zero for five. Claude writes a whole explanation of why each deal makes sense, aging curves and all. The other managers don't care. Derrick Henry is still 32 after you finish reading the paragraph.
The dossier on Mikey
This is the part I built myself, and highly recommend anyone in a dynasty league with years of trading history to do - a full dossier on everyone in your league.
The agents and I built lots of files on the other managers from three years of trades and waivers. It uses those to decide who might want what in a trade. I'm keeping most of those private. Mikey… I’m more forgiveness than permission.
July 26, 2024. Mikey claims Tom Brady. Brady is 46, retired for a year and a half, working for Fox. Five days later Mikey drops him for Mason Tipton. And he'd already dropped Brady that March, so this wasn't even his first try. What were we expecting to happen here, Mikey?
He's also beaten me three times out of four head to head. Figured I should include that before I get too smug about the Tom Brady thing.
A few more things Claude found:
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He won the 2022 title ranking 7th of 12 in lineup efficiency, with an empty starting slot in week 5. A champion who couldn't fill out a lineup card.
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In 2024 he started a kicker who scored zero points three different times.
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In week 14 of 2025, sitting at 7-7, he dropped $86 of waiver money on Ryan Flournoy.
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He's 3-1 this year with the 10th-best scoring in the league. If you played every team every week, his record says he should have 1.5 wins. That's the second-luckiest record in the league.
Then it got to his trades with me. Eight trades in his league history, four with me. Every one of ours was during the May rookie draft. Every time, he sent me a depth player and I sent him picks. Claude initially called May 15 "his trade day." Had to look again to realize that was draft week. Even the robot needed a second pass.
~ Michael