Rewind: The Gray Area of Fantasy Football artwork

Rewind: The Gray Area of Fantasy Football

The Late-Round Fantasy Football Podcast

June 16, 2026

It's another rewind week, where JJ brings back an old evergreen episode that's still relevant today. This week? It's all about the gray area of fantasy football. Make sure to check out LateRound.com to pre-order the 2026 Draft Guide. And while you're there, become a member!
Speakers: JJ
**JJ** (0:11)
Hey guys, JJ here with another Rewind episode. Many of you probably remember this, but last year, there was a controversial dynasty trade that I did in one of my leagues, and then I talked about that move in a newsletter. That newsletter was then pushed to social media and onto Reddit, and people ended up talking about it a whole lot more than some of my other content. And honestly, it was a really fun conversation. I enjoyed people's takes, people disagreeing with me, people agreeing with me. This is what fantasy football is all about. And I think it's my job to, yes, give you guys advice, but also make you think differently about this game. But the response to that newsletter pushed me to do an episode on the gray area of fantasy football. It was an episode that really came from the heart, as silly as that sounds. I approached this game in a specific way, and this trade really opened me up to explain my thinking in a more detailed manner. And that's what this episode is really all about. Playing these rewind episodes back are always really interesting to me. Because there's no hiding from takes. They're all out there. You can see exactly what I was thinking in that moment. And you can see how right or wrong my forecasting was. In this case, there are things where I feel great about the process, and there are things where I'm surprised at the result. Regardless, I think this is an evergreen episode that we realistically should visit almost every single year. It's an important part of my process, and it's a great way to wrap your head around how I think about fantasy football. So without further ado, here's the episode on the gray area of fantasy football.
Every once in a while, I do episodes like this one where I kind of just go. I don't have the clearest goal in mind when I put together my little show sheet. But I know there's a general message that I'm trying to get across. And today's message is the following. We need to get away from this black and white thinking that's rampant in fantasy football. Maybe it's hot take culture taking over. Maybe it's the fact that clicks are more important than more genuine content. Whatever the reason, the fantasy football world seems to be losing the gray area, when that's the opposite of what actually should be happening. As we mature with this game, as this game becomes more and more popular, and we become more and more interested in it, you would think there'd be more recognition to the fact that variance is everywhere within it. Like, I've been around for a while now. I've been doing this as my job for 12 years at this point. I sort of grew up in the fantasy football space starting when I was in my early 20s, childless, living in an apartment with my girlfriend who's now my wife, thinking I had the answers when I had none. And trust me, I know that 12 years from now, I'll be looking back at this exact moment, probably saying the exact same thing. But as I've watched the fantasy football space grow into the awesome community that it's become, I've seen aspiring fantasy analysts pop up and gain popularity. And something that I've noticed with those up and coming analysts is that the first year when that analyst gains a significant platform, when they're able to talk to thousands of people for the first time, that first year is always full of insane confidence. They fire takes out there like it's no one's business. But that first year humbles you, man. You realize that when you start to put yourself out there, that means you're putting yourself out there to be both right and wrong. And when there's more pressure to be right, and when you're then inevitably wrong, you realize on a much deeper level that this game of fantasy football that all of us love, it's impossible to bat a thousand, even if everything seemed to line up perfectly prior to the start of the season.
After that first year, you go from having more black and white takes to realizing that this game, it lives in the gray area. There's really no need to say, this absolutely will not happen. You're not scoring fantasy points based on those bold outcomes. Instead, you start to add words like probably and likely to your everyday vocabulary. Your take goes from, he's definitely gonna finish as a top fantasy producer, to he's probably gonna finish as a top fantasy producer. Because you know that in this game, anything can happen. Anything. Now, I bring all of this up because just a couple of weeks ago, less than a couple of weeks ago, I made a trade in one of my dynasty leagues. It's one that's filled with other analysts. It's a 14-teamer, there are deep rosters, it's a league for sickos. But in that league, it's a super flex league, my roster's loaded at wide receiver. It's fine enough at tight end, the quarterbacks are iffy, the running backs are super iffy. Now to anyone who's listened or consumed my content over the last week or so, you probably know where this is going. I brought it up on Perspectives with Jeff Bell last week. I wrote about it in my weekly newsletter, which by the way, totally free to subscribe over on lateraound.com. But going into that league's rookie draft, I had the 106 where I'd planned to take Trevion Henderson, a perfect addition to my roster. But I knew that I wanted to bulk up at running back because this draft class is filled with talented runners. So I made the following move. I traded away Roma Dunze, and I received the 8th overall pick in the rookie draft, the 108

20 more minutes of transcript below

Feed this to your agent

Try it now — copy, paste, done:

curl -H "x-api-key: pt_demo" \
  https://spoken.md/transcripts/1000651996090

Works with Claude, ChatGPT, Cursor, and any agent that makes HTTP calls.

From $0.10 per transcript. No subscription. Credits never expire.

Using your own key:

curl -H "x-api-key: YOUR_KEY" \
  https://spoken.md/transcripts/1000772940637