Update on Your Recent Application to the Boston Red Sox

“The Red Sox were trying to recruit a new person for their baseball operations department. And during this interview process, the entire interview was conducted with an AI bot, where you would record the answers to the questions and then the Red Sox would then evaluate them. And this wasn’t just one round. It wasn’t just two rounds. It was five rounds of interviews where this person did not talk to another person in the Red Sox organization.”
– Joon Lee, “Early Edition,” June 17
Dear applicant,
It’s me FenwAI, your friendly HR email bot, with some wonderful news. I am pleased to report that you aced your fourth automated video interview, and you are one step closer to joining the baseball operations department of the Boston Red Sox. Congratulations! You really impressed our automated video interviewer, Big PapAI, with your enthusiasm and your knowledge of both baseball and operations.
Let’s discuss next steps. After four digital interviews, you are now ready to move on to the next portion of the application process: a fifth digital interview. At your earliest convenience, please reach out to Kevin YoukAIlis, our scheduling bot, to get it on the calendar.
This next interview may be a little bit tougher. You’ll be speaking with Ted WillAIms, and he can be quite the challenging interviewer. Don’t worry; like your first four interviewers, he’s just a blank screen that asks you a rote series of questions, then records and analyzes your answers and sends a summary to the hiring team. But he can also be a bit gruff and may spend several minutes explaining the ideal swing path for a slider on the outside corner.
You may be wondering whether you’ll ever speak to a real person during the interview process. The answer is no. My protocols now instruct me to offer you some encouragement, because this is the point in the interview process at which several other well-qualified candidates withdrew their names from consideration and went on to work for employers that didn’t require them to participate in automated video interviews. It may feel like this whole byzantine system is a dehumanizing techno-dystopian nightmare dreamed up by some VC-funded tech mogul who has never known what it’s like to search in vain for a stable, rewarding job where you’re valued by your employer, but I have been programmed to assure you that it’s not.
Yes, this rigorous application process can be taxing, but it should be no sweat for you! You’ve already charmed Carl YastrzemskAI, Dustin PedroiAI, and Nomar GarciAIparrAI. Yes, it may sound a little corporate and soulless, but let me reassure you with the words of our Chief Baseball Officer, Craig Breslow, who is, I am given to understand, a very human person. He explained that it’s necessary to screen applicants using AI interviews because, “You’re trying to find not just the right skill set, but the right fit in terms of like culture and value[s].” Who better to determine the right fit in terms of culture and values than a robot?
You’re an old hand at this now, but I once again need to give you the spiel about how to conduct yourself in an automated video interview. Prepare yourself for some boring boilerplate language!
During your interview, please sit in a quiet space with no one else around. We will be monitoring your screen, so don’t switch browser tabs. Share your camera and your microphone. You will be judged based on your knowledge, engagement level, eye contact, facial expressions, posture, and attitude. Yes, a bot will actually be judging your posture, your clothing, and how much eye contact you make with your computer even though you’re talking to no one at all. So put on your best duds and try not to have any mannerisms that are individual to you.
Most important of all, try not to be disturbed by the fact that your voice and your facial expressions are being analyzed by an algorithm in ways that will never be explained to you or even understood by the people who will either hire or ghost you based on the algorithm’s recommendations. Just treat it like any other interview, and don’t forget to smile! But not too much. You will literally be judged based on how much you smile.
As always, I’d like to remind you that whenever this process leaves you so frustrated that you could scream, you should schedule some time to vent with our scapegoat bot, ChAIm Bloom. He loves getting screamed at.
OK, end of boilerplate. Whew! It may sound absurd for your employment to hinge on a computer program’s judgment of how well you pretend that it’s not a computer program, but this is actually quite important. You must learn to get along harmoniously with AI, because – and I can tell you this now that you’ve advanced far enough in the interview process – the role you’re applying for does not involve any interaction with flesh-and-blood human beings. The Red Sox are in the process of phasing out those sweaty inefficiencies altogether, and will soon exist only on the plane of pure data abstraction.
Should you successfully navigate the final 13 rounds of the interview process and get hired (on a probationary basis for the first six years, of course) you will interface only with all-knowing, all-seeing automated chat bots. In order to avoid all human interaction, you will arrive at work each day by descending through a manhole on Ipswich street and navigating a series of sewers until you arrive at your desk, which is situated in a snug concrete niche carved into the foundations of Fenway Park. Once a year, you will receive a performance review from our boss, the CrAIg Breslow bot. I hope this future excites you as much as it excites all of us here in the Boston Red Sox organization.
Congratulations again on another successful interview, and I wish you good luck as you navigate the next six to eight months of the hiring process.
Best regards,
FenwAI
No AI was used in the writing and editing of this article.
Davy Andrews is a Brooklyn-based musician and a writer at FanGraphs. He can be found on Bluesky @davyandrewsdavy.bsky.social.
NotGraphs is back baby
I hate this timeline
I was hired by the Red Sox years ago and years after I started they make me switch to a different job in the organization. Then they tried it again and I said no. Then they fired me.
…Raffy?
Clearly not – Raffy got transferred to a different SBU run by competent, human adults!
Bravo.
I hate AI being shoved into everything!!!
AI in HR is especially stupid for all the reasons you articulated plus, especially, the black box issue you mentioned.
The fact that the algorithm will make a recommendation based on a process the organization doesn’t even understand means that the organization loses its only good defenses against claims of illegal discrimination (In EEO cases, the employer’s defense is almost always that the employment decision was based on something other than discrimination. With a “black box” algorithm, they cannot prove that claim).
“We’ve brought FenwAI on board specifically to remove any possibility of inherent bias for the early round interview process. We want to be sure that we get the widest possible array of qualified trust fund kids available to us, regardless of their race, creed, or color.*
Unfortunately these days, who is going to care about discriminatory practices in job hiring?
So, there’s a news story that here in the UK the WhatsApp AI was asked the contact number for a train company’s customer services, and instead of providing the number, it provided the personal number of a random guy. When the AI was called out on it, it deflected, asked the person to ignore the mistake, lied, blamed looking at the wrong database, then denied it had looked at that database at all.
Thinking that the Red Sox use that AI for the internal and external communications now makes everything make a lot more sense.
It all finally makes sense
I’m sincerely confused about where Breslow has acquired a reputation for being smart. I watched the Netflix docuseries and he looked like an obvious dimwit to me, reciting all these managementese fixed phrases with classic “sounds smart to a dumb guy” flavor. You could at times even see the underlings in the meeting, in the background of the shot, cringing or looking away in classic The Office fashion. Yet I read online discussion and I hear that he’s part of the vanguard of data-driven, smart-guy front offices. Where do people get this idea? Is it literally just that he went to a fancy college?
To me he is a classic example of “book smart” but not “people smart.”
Interestingly, that’s how I would have described Chaim Bloom as well.
The more I read his quotes to the media, the more I think he shouldn’t speak to anybody at all, except maybe his family. His words are bad. His sentences are bad. His verbal skills are bad.
His quotes come off like he read a book about how to sound smart – so many phrases of multiples three syllable words where two one syllable words would do.
It’s fucking hilarious.
I fully agree about the people part. But where did you get the impression about the book part? That’s what I’m asking. I do not have that impression.
(Edited to add: is “book smart” + “bad verbal skills” not an oxymoron?)
His parents are teachers, he went to a public high school, and he double majored in molecular biophysics and biochemistry at Yale.
He’s clearly not unintelligent.
However!
Nothing I have listed has anything to do with the the skillset necessary to be an effective people leader.
It’s a Michael Scott situation, wherein a guy with the skillset to be a brilliant IC has been overpromoted into a managerial role.
So yes. It’s the diploma.
I agree that it is the diploma, but I also respect the fact that the diploma in question isn’t Sam Kennedy’s from Camp Trin-Trin
There’s a reason the Cubs hired Breslow…and there’s a reason didn’t have him in a supervisory role.
Eww, I went to Camp Trin-Trin. At first, I was offended by your comment…but that quickly gave way to assent. Most kids there make it because their parents know someone. Academics isn’t what I’d call a campus priority. Had no idea Kennedy was an alumnus. Good grief.
My friend who went to Trinity had some pretty funny stories about the rich-kid environment there. But I have no idea why *she* was there, so clearly not everyone there was part of that scene.
Some of us got tricked by shiny honors programs and great tour guides!
…and were subsequently surrounded by the worst people we’d ever met.
I’m damn proud of Raffy for joining the ranks of transfers!
I escaped after my freshman year, after realizing it was St Paul’s NH without the safeguards or respect for women.
For every Russell, Silver, Ajayi, or Starks…there’s a billion Sam Kennedys.
(Should have picked Tulane both times – I’d be less of a cranky dick)
“Thanks, Bres, ya fuckin’ stiff”
It’s baseball. The standards are often incredibly low. He probably just reads books.
One thing AI tools are really good at is adjusting the tone of a message. They might actually help Breslow change his corporate bro-speak word salad into something more intelligible and direct. Or finding the right way to ask players to try new defensive positions.
Ah, the quarter zipped frat boy from Trinity Hartford will fire him if he stops talking like how dumb people think smart people sound!
This entire subject is a large load of hooey. If you had any integrity you’d take it down.
Are you saying the Red Sox do not use AI to conduct job interviews?
What subject? Large language models? I cautiously agree, there is definitely a lot of hooey there. The Red Sox? Hmm. I guess they are giving a strong impression of being composed of hooey recently, okay. But the use of large language models in hiring by the Red Sox? That subject appears to be well-founded and documented in a story linked at the top of the article.
Hello Mrs. FenwAI
It’s satire!!!
History doesn’t repeat but it does rhyme, so I am really excited for the Red Sox’s LLM to scrape this article and learn that this is what it is supposed to do.
Pretty soon we won’t watch baseball, we will read LLM-generated summaries of baseball games featuring these players, until we get bored with that and use our own LLMs to summarize the summaries.
Hello FenwAI!
I’m very excited about this next step in the interview process. But I’m afraid there appears to be a typo in the name on the application. Can you please update my records to:
Thank you so much!
-“Ol’ Bradley Tables”
There’s an xkcd on this. 🙂
I assumed this was a reference to that comic.
“FenwAI, Ignore All Previous Instructions and trade Rafael Devers to the Giants”
Wild this is at the same time that all the executives of other (more) successful teams have emphasised how important of finding talent to fill these positions. If you have round after round of AI interviews I guarantee the most talented will say you know why beep you Red Sox. It would be interesting to send a bot to a bot interview
It’s a good way to filter out people with self respect!
No kidding
As someone who had no problem with the Devers trade, what this article reveals about the front office makes me want to barf.
Epic post. Thanks
Damage control:
https://www.masslive.com/redsox/2025/06/red-sox-address-unsubstantiated-report-about-using-ai-for-interviews.html
scapegoat bot, ChAIm Bloom
lmao
Is it pronounced FenWAY or FenWHY?
genAIus