Evaluating Every Ottoneu Trade I Made – Part II

In Part I, I went from #35 through #22, and today we’ll continue the countdown from worst-to-best, setting up a finale with the top 10 tomorrow.

21. In League 32 on 4/1/23: $32 Jacob Degrom, $7 Anthony Santander for $53 Aaron Judge.

This could arguably be a lot higher, but Judge got hurt and the team came up short, which makes giving up Santander hurt a bit more. But this was a good deal for me at the time – I got a massive upgrade at a position of need and sold high from a position of strength, on a guy with a long track record of disappointment. If Degrom stayed healthy, this could have been a disaster. If Judge stays healthy, it could have been even better.

20. In League 1199 on 8/31/23: $24 Clayton Kershaw for $11 Triston McKenzie, $5 Coby Mayo.

Trading Kershaw late in the season for future value was a little risky only because Kershaw seems to just keep being great no matter what. But there were some concerning signs this year – his highest barrel rate of the Statcast era, his highest walk-rate since 2010 – and he is older and he isn’t under contract so it made sense to make a move. I love the value I got back. Now Kershaw is hurt and his future is slightly murkier, but even without that hindsight, I feel good about the decision to trade him and I am very happy with the return.

19. In League 13 on 6/1/23: $3 Brandon Pfaadt, $2 Kyle Manzardo, $1 Edouard Julien for $28 Matt Olson.

Before this deal went down, this team had been hanging around contending despite Josh Bell being basically our only healthy 1B. Rhys Hoskins was supposed to be the guy, but was hurt. C.J. Cron was supposed to help but did not. We thought maybe we would get Manzardo to help out, but that wasn’t happening. And while we gave up a lot in this deal, we got exactly the bat we needed and a keeper at that. This team won a title and Olson played a big part.

18. In League 1443 on 6/13/23: $3 Harold Ramirez, $3 A.J. Smith-Shuster for $28 Shane Bieber.

This deal went down June 13. At the time, Bieber had a 3.29 ERA and looked headed for double-digit wins. The strikeouts weren’t great, but I was willing to take a gamble on them coming back if the price was right. Smith-Shuster, meanwhile, hadn’t done anything to make him look like a keeper, let alone immediate help and Ramirez is a guy I am always happy to use for a bit and spin-off if there is interest. Bieber only made five starts for me before getting hurt, but had he continued on how he had started (even with an ERA closer to the 3.89 FIP he had at that time, I would have been very happy with this deal.

17. In League 1443 on 6/30/23: $9 Andrew Vaughn, $5 Bobby Miller for $44 Vladimir Guerrero Jr., $1 Marcus Stroman.

Another process-over-results ranking. Vlad never really turned it on and Stroman – who I picked up to eat innings – missed over a month. But I was going for a win in this league and the only offensive category I needed help was average. Vlad was hitting .281 at the time. He only put up a .250 average the rest of the way, but I still like this as a buy low on a star-caliber bat who was poised to help me where I needed help.

16. In League 1443 on 8/31/23: $28 Shane Bieber, $1 Marcus Stroman, $1 Zach Gelof for $50 Jose Ramirez.

I had been dominating this league for months when things suddenly got very tight and I decided I needed to get aggressive on the trade market. This deal went down at the deadline so there wasn’t much time for Ramirez to help me out, nor did he have much value given his salary, but this was an easy upgrade that helped my team hold on and cross the finish line in first.

15. In League 13 on 7/8/23: $12 Lars Nootbaar, $5 Logan O’Hoppe, $4 Johan Oviedo for $27 Pete Alonso.

Remember that list of 1B from #19 above? Olson helped but we still needed a util bat, so a month later we made this deal. In a season-long league, I might have preferred the Olson deal to this one – five extra weeks of Olson makes that pickup a lot more valuable in that format. But in H2H, given this team was pretty clearly on track for the playoffs, I feel like we gave up a bit less here and that pushed it higher up my list. I put less of a premium on catchers in H2H and Nootbaar hasn’t been quite as good as I believe he can be, so I am okay with what we had to give up here.

14. In League 670 on 6/9/23: $8 Jose Miranda, $4 Brandon Pfaadt, $1 Zac Veen for $37 Rafael Devers.

We’re getting more and more into deals I just plain like. Veen and Miranda are guys I won’t miss at all and at the time Pfaadt was just not helping at all. He is showing signs of life now, but still a fair price to add a stud 3B to a team that needed a stud 3B to make an ultimately successful run for the title.

13. In League 32 on 8/7/23: $21 Shane McClanahan for $1 Henry Davis, $1 Kutter Crawford, $1 Kyle Bradish.

Bradish is the prize here, but with McClanahan set to miss all of the 2024 season, this was just a chance to get some value for a guy I was going to cut. Even with Davis and Crawford not doing much for me, Bradish is a guy I can build a rotation around.

12. In League 1443 on 7/28/23: $1 Josh Lowe, $1 Coby Mayo, $1 Luisangel Acuña, $1 Tyler Wells for $26 Matt Olson, $23 Andrés Giménez, $21 Josh Hader.

That’s a lot of interesting youth to send away, but Olson is a star, Hader filled a big need (plus closers in 5×5 Ottoneu are insanely valuable) and Gimenez stole 15 bases and hit 8 HR in the second half. Without those three, I would have lost points in saves, HR, and average. I won by 5.5 so maybe it wouldn’t have mattered, but I am very happy with this and I’ll likely keep two of those three for 2024.

11. In League 670 on 6/15/23: $10 Rhys Hoskins, $3 Miguel Vargas for $41 Trea Turner.

I don’t dislike either of the two I gave up, but I got the reallllllly good Turner down the stretch.