Oral History of an Ottoneu Blockbuster

On June 29th, as the clock neared midnight ET, Jake Mailhot and I completed a trade in League 32 that saw us swap a couple of big names.

The way this trade went down is somewhat interesting and is a useful demonstration of how to negotiate and trade in Ottoneu. Rather than just write up what happened, Jake and I are going to tell the story of how this blockbuster came together.

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Chad Young: Anytime I look back at trade talks I’m always surprised at the route they take. This one started with me commenting to you that I was interested in two guys on your block – Ian Happ and maybe Clarke Schmidt. Neither of them ended up in the deal! Full disclosure, I had [Corey] Seager and [Reid] Detmers back of my mind but neither was on your block and I wanted to start with something that would get you engaged. Sometimes I start with a name I know the other person likes and it cuts off discussion too soon.

Jake Mailhot: Well, your strategy worked out. I wasn’t in a rush to move Happ — I wanted to get back close to full value on him since he’s perfectly keepable at $12 — but Schmidt was definitely someone who I was happy to trade since he really hasn’t taken a step forward like I had hoped this year. There were a few pieces on your trade block that interested me, specifically some cheaper outfielders to essentially replace Happ’s production at a lower salary. And then I also asked about Tarik Skubal who wasn’t on your block but seemed like a nice target since he was coming back from his injury relatively soon and I’ve really liked his stuff.

CY: I have had a hard time with Skubal because his trade value is all over the place. I really like him and don’t see him as just a throw-in type but people have pretty consistently treated him like that’s all he is. You didn’t just ask about Skubal though, you asked if you could “pry him” away from me. Let me know you weren’t just trying to steal him, but knew I’d need real value.

And that lead to the first real offer – Josh Lowe and Skubal for Happ and Schmidt. And I just wasn’t feeling it. Felt like a lot of lost future value for not a lot of immediate improvement.

Also, I should be clear, when I say I had those two back of my mind, I didn’t mean that I was planning or hoping to get them all along. They were just a couple of names, among many, that I liked but weren’t on your block. Didn’t ask about any of them at first.

JM: After that initial two-for-two offer, you countered with the pair of Happ and Schmidt for just Skubal. In my mind, that felt like a straight one-for-one swap of Happ and Skubal with Schmidt thrown in to help you hit your innings-pitched cap. I thought that counter held a little too much risk for me; Happ is a consistent producer at a reasonable salary while Skubal was coming off a serious injury. You asked about a few of your bubble starters to see if we could bridge the gap and make it a two-for-two deal again. Ben Lively 라이블리 and Louie Varland are each interesting in their own right, but neither of them look like keepers for 2024 so they were non-starters for me.

CY: Yeah I can’t blame you on either of those two. I’m annoyed about Varland cause I gave into the hype around him when I acquired him a couple of weeks ago. I get the Stuff+ numbers and all that but there’s really no evidence he’s, you know…good. But there’s still interest in him so I keep shopping him at least for now. Lively I think I even said I didn’t expect you to like. This was purely “do you just need a little something extra” and I definitely understand why this didn’t help. We also kicked around someone from my 5MILB list (well, I kicked it around) but I think we were just too far apart on Happ vs Skubal, so we went back to Lowe coming to you and this is the first time Detmers came up. Swapping out Schmidt as a throw-in for Detmers who I actually like in a Lowe/Skubal for Happ/Detmers offer. Then it was your turn to try to downgrade what I get back! Nothing crazy but you wanted to just move down from Detmers or Happ.

JM: I really like the progress Detmers has shown this year and it feels like he’s taken the step forward to become a reliable mid-rotation starter. I really didn’t like the idea of giving him up, even if I was getting Lowe and Skubal back. I tried to offer Marcus Stroman instead and I was genuinely surprised you didn’t go for that. Stroman is one of those guys who really has a lot more value to a real-life roster than in a format like Ottoneu but he’s in the midst of a fantastic season with the lowest FIP since his rookie year.

CY: I think you just had a little bad luck offering me Stroman to be honest. I’ve always been lower than others on him and I just don’t trust that there won’t be regression on his HR rate. His GB rate is up but his HR/FB rate is WAY low for him despite giving up harder contact this year, and Wrigley changes shape in the heat of the Summer. Meanwhile Detmers I have really liked for a while and I think he brings more to the table – peak Detmers is more valuable than peak Stroman because of the strikeouts

JM: Which is exactly why I wanted to try and hold onto Detmers.

CY: In retrospect, maybe I should have just taken Stro but I’m happy where it ended up. Honestly, this might be fallout from Varland. I had just taken a guy via trade who I don’t like because it seemed like I should like him. I wasn’t excited about doing it again.

That’s maybe unfair – Stroman is way more valuable than Varland of course. But conceptually I prefer not to trade for guys I’m low on, even if I still think they’re good (like Stroman).

JM: And I totally understand that; when you’ve got the option, it’s better to have a guy you like on your roster than settle for someone you’re not excited about. Anyway, we took a little break from negotiating after that and I came back a little while later with another option: swapping in Lourdes Gurriel Jr. instead of Happ.

CY: And I didn’t love that but in a different way. Lourdes is so hot and cold and I really wanted the steady Happ production. But Gurriel, value-wise, made sense if I was going to get Detmers.

JM: And again, I thought Gurriel’s recent production would help tip the scales; he’s really only had one lengthy cold spell this year and he even homered as we were negotiating!

CY: Of course he did! And given I know how hot he can get I was suddenly more intrigued. But that conversation about his hot streaks is when I had to ask if Skubal and Lowe got me close to Seager. He’s one from your article on your rebuild I knew you weren’t LOOKING to move, but maybe would.

JM: I knew the Seager question was coming at some point. Since acquiring Seager for Bryce Harper a month ago, I had a bunch of teams inquire about him. Most of those other offers were about quantity of prospects rather than a few high-quality pieces and I was really looking for star-level production if I was going to move him. He’s been one of the best hitters on the planet this year and his salary was close to fair value if he continued to produce like he has. I wasn’t about to move him for a handful of far-off prospects who may or may not pan out and who definitely wouldn’t replicate his level of production at their peak. With all that in mind, I dropped the bomb that completely shifted the conversation: what about a Seager for Aaron Judge swap? I knew you were looking for as much production as soon as possible since you’re currently in first the league and Judge’s timeline was still very much up in the air.

CY: I had Judge in two leagues and I’m contending in both. In this one, I had swapped Jacob Degrom for Judge right at the start of the season so I ended up ahead but I needed production now. In the other league, I swapped $56 Judge for $51 Vladimir Guerrero Jr. And Pete [Ball, my co-host] and I had talked on Keep or Kut about swapping Judge where you can get elite production. So I was very interested in that idea. I love Judge. I think he’s without a doubt the best player in this format outside Shohei Ohtani (and the best hitter even including Shohei). But if I want to win this highly competitive league, I need to keep producing and I worry Judge could be out a LONG time. There’s risk (I guess risk) that Judge is back soon and I could’ve just waited, but Seager is really good and my OF is pretty strong relative to my MI. Honestly, I would have done that 1-for-1 with the two studs without blinking, but I figured that wouldn’t quite work for you. Was I right?<

JM: I would have seriously considered a one-for-one swap of those two superstars. Judge is only $5 more expensive than Seager in our league and I think the difference in production between the two of them is a lot more than $5 when they’re both healthy. I was happy to take on the risk that Judge would be out for a lot longer this season since I’m mostly looking forward to 2024 anyway.

CY: Maybe I should have just offered that! As it was, I figured you’d need a little extra and since I thought the last 2-for-2 (Lowe and Skubal for Gurriel and Detmers) leaned a little your way, I thought maybe merging the two would make it work for you and still be good from my perspective too.

By the way, Skubal looked great in his first start back. Think we were both right to value him highly. I still think he can be special.

JM: Thank goodness he looked so good. Elbow injuries are always scary (not as scary as shoulders for pitchers though), so it was so nice to see him so dominant in his first start back, even if it was against the A’s.

After you proposed combining the two offers, I was pretty sure I was on board at that point. I made up some excuse about “having to math out” what my roster looked like with Judge on board but I was really just taking a moment to make sure my initial gut feeling was right. The difference between Judge and Seager’s salaries was negligible and I was happy to keep the latter so I had no problems with the idea of keeping Judge for next year. And Judge helped bridge the gap I was feeling in giving up Detmers in that two-for-two swap we were batting around. In the last article I wrote about my current rebuild, I said that my biggest concern heading into next year was the amount of salary I was planning on keeping on my roster. Adding $2 Lowe and $1 Skubal definitely help in that regard and I was able to replace Seager’s superstar-level production at a similar salary. The fact that I was moving that production from SS (where I already had Wander Franco) to OF was just icing on the cake. Win-win-win in my eyes.

CY: Yeah looking back our rosters were ideally set up for that swap. Seager and Wander can certainly coexist on a roster but in a rebuild that’s a luxury you can use to make a move. Meanwhile, my MI was Isaac Paredes, Andrés Giménez, Willy Adames, and Jeremy Pena. Paredes has been good and Giménez has been great lately but that group lacks an elite anchor. Meanwhile, my OF included Kyle Schwarber, Luis Robert, Nick Castellanos, and Bryan Reynolds and I had some depth and was nearing a deal for George Springer to replace Judge (at least as much as he can). So even long-term I could take a hit to my OF for SS help.

And I think that’s sorta it. You still feeling good about the deal? I still like it.

JM: Yeah, I’m feeling good about it. Judge is definitely a better fit on my roster and Lowe and Skubal are really nice bonus pieces. Looking back on the negotiations, it’s kind of funny how much it escalated from where we started to moving two superstars. The “obvious” move was right under our nose but it took a while to get to a point where it was on the table. Trade negotiations sometimes go that way where the endpoint looks a lot different than the starting point, but sometimes it takes considering all the options on the table with your trade partner before what you’re really looking for emerges.