Not every decision is a winner. That’s especially true of fantasy trades. In keeper and dynasty formats, there are so many moving parts that the “winner” of a deal won’t be known for years – even if your leaguemates will often express kudos or dismay based on present impressions.

Sometimes, a good process will parlay into a bad result. And on occasion, you just think you’re using a good process when in fact you’re making a devastating mistake. Today we’ll review my three worst trades of the last 18 months. These all occurred in the 20-team industry dynasty league The Devil’s Rejects. I co-manage the team with former RotoGraphist Chad Young. However, I was the architect for all three of these deals. Chad merely signed off. They’re my responsibility.

You’ll notice the motivations behind them are very different…

January 22, 2018

Outgoing: Alex Kirilloff

Incoming: Yuli Gurriel

This was a classic prospect for win-now asset swap. Kirilloff was at a low point after missing the 2017 season. Gurriel was on the rise after a shiny postseason display. However, he’s old by dynasty standards which drove down his price tag. As I recall, even though I liked Kirilloff, he was in danger of being left off our 28-man keeper list. Gurriel was more immediately useful with his multi-position eligibility.

Ultimately, this is an example of what I discussed on Monday. I traded what was at the time a frontier prospect for an undervalued asset to help me contend. This is a battle tested process, but you will run into results like this. My favorite part of was this message I received from Chad:

Gurriel was a frequently used sub in our third-place 2018 campaign. At the time, I thought we desperately needed depth. In retrospect, I wish I could undo this swap. It’s not a big deal. It gets much worse from here.

January 15, 2018

Outgoing: Mookie Betts, Ben Zobrist, Chris Devenski, and a sixth round pick

Incoming: Jose Altuve, Yonder Alonso, Adrian Beltre, and a third round pick

This disaster came a week prior to the Gurriel gambit. Zobrist and Devenski were on the wrong side of our cut list so we viewed this as Betts for three players and a modest pick upgrade. We tried to hold out for Ketel Marte instead of Alonso, but it wasn’t happening. It turned out not to matter a whole lot.

Chad and I figured Betts and Altuve were roughly equal in 2019 with Betts obviously having more future value due to his age. However, we were also starved for a second and third baseman, and we’re not adverse to bankable old guys.

Obviously, this went sideways pretty quickly. Betts discovered launch angle and destroyed the world. Altuve was merely good and battled a knee injury. At least his prognosis is very positive, and he’s still on the right side of 30. We hemorrhaged value in this swap – Betts is easily worth two Altuves now.

Our earliest asks were for two of Jose Ramirez, Freddie Freeman, or Altuve for Betts and a lesser piece. That scenario would look fine in retrospect.

As consolation, on December 20, 2017, this same owner traded us Patrick Corbin for a fourth round pick. The mistakes weren’t entirely one-way. Betts for Altuve, Corbin, Alonso, and Beltre’s victory lap looks reasonably plausible.

As much as I’d like to chastise myself for this one, I don’t think we could have anticipated the Betts hyper-breakout. That was a top 1% outcome. Regression for Altuve was expected, but that was baked into the acquisition cost by upgrading two other roster spots. I won’t say we used a good process here – it’s always suspect to trade one player for many. I’m just not sure it was a bad process either. We had outfielders, we needed infielders – a classic surplus-for-needs swap.

August 1, 2017

Outgoing: Eugenio Suarez, Carter Kieboom, Jesus Sanchez

Incoming: Bradley Zimmer, T.J. Friedl, and Hunter Strickland

This one deserves a classic “oh no.”

There’s some context to unpack. At the time, we were battling for fifth place which in this league comes with a $100 prize (the cost of entry). We had an outside shot at third place ($400 prize) but needed to make up ground in stolen bases without giving away points in other heavily contested categories. In short, we needed a top-of-the-order power hitter with speed.

At the time of the trade, Zimmer was a 24-year-old batting .282/.345/.464 with eight home runs and 13 stolen bases over 232 plate appearances. He hit leadoff most days. He was everything we needed. We knew we were overpaying in prospect value – we knew Suarez for Zimmer should have been enough. I even published on the topic (somewhere) at the time. To us, the potential to gain of $100 to $400 was well worth the loss of future value.

After we acquired him, Zimmer hit a miserable .144/.220/.200, singlehandedly trying to ruin out bid for contention. Through a series of miracles, we managed to squeak out a third place finish with the help of waiver wire pitchers. No thanks to Zimmer!

This still could have worked out if Zimmer rebounded in 2018. Alas, he failed to show up, and his status for 2019 is up in the air. Based on current dynasty drafts, he’s not a top 400 asset. Meanwhile, Suarez, who Chad and I have strongly believed in forever, finally took that big step from core performer to star. Kieboom is a top 15 fantasy prospect. Sanchez is in the top 50.

It was a mistake to fall for the shiny glimmer of a cash prize – especially since we got it anyway. By losing Kieboom and Sanchez, we missed on some massive offseason bargains in prospect-for-veteran swaps. And not having Suarez on the roster baited us into taking that Betts deal.

The fallout from this error was catastrophic and greatly reduced the value of our franchise. We won’t make this mistake again.