Let’s take a brief moment to go over something which doesn’t come up very often, but is exhilarating and scary when it does: The Challenge Trade. There’s a good reason why you almost never see two MLB teams trade a prospect for a prospect – neither team wants to be the one that misevaluated their own guy. Probably the closest thing we’ve seen to this in recent memory was the Yankees/Mariners trade last off-season which sent Jesus Montero and Hector Noesi to Seattle for Michael Pineda and Jose Campos. But still, not the same, since Pineda, Montero and Noesi had all logged major league time.

As the trading deadline approached in the league which is the focus of this series, I pulled off a challenge trade with another rebuilding team. When this happens in dynasty leagues, it’s almost always with guys whose stocks are falling – and this was no exception to the rule. You just have to keep the faith in your own evaluations and hope that the chips fall right for you. Here’s my challenge trade:

I dealt Brett Jackson and Ethan Martin for Shelby Miller and Brian Goodwin. (7/31/12)

I had tried to include Jackson in many deals since I took over this team, since I firmly believe that his trade value will never be higher than it was before he would get called up to the majors. On the other hand, I also believed that Shelby Miller is the anti-Brett Jackson – a player who’s value would only go up from what it was in July. At the time of the trade, I considered Miller a better dynasty league prospect than Jackson, and that’s not even taking into account the fact that it’s a points league (which makes Jackson’s value lower due to the negative counting of strikeouts).

And that’s just dealing with the two main pieces of this deal. I am one of the drivers of the Brian Goodwin bandwagon and was thrilled to get him. I ranked him in my Top 100 Dynasty League Prospects coming into the season (#77, I believe) and he’ll only be higher on the 2013 list. With Jackson maintaining his eligibility, I expect Goodwin to place ahead of Jackson on next year’s list. And again, due to this being a points league, that difference will only be exacerbated in terms of true league value. Ethan Martin is an arm with some upside, but he’s really just a flyer at this point. Even if he clicks, this trade can still work out in my favor.

So now there’s nothing left to do besides wait and see how this plays out. There’s no way to know whether this trade was the right move or not until at least three to four years down the road (and that’s just because all of the players involved are at least in AA).

How do you think I did? Would you have made this move back in July? Would you make it now?

Rebuilding a Dynasty League Roster, Part 1: Setting the Table
Rebuilding a Dynasty League Roster, Part 2: Establishing Your Time Horizon
Rebuilding a Dynasty League Roster, Part 3: The Evaluation Stage
Rebuilding a Dynasty League Roster, Part 4: The Opening Trades
Rebuilding a Dynasty League Roster, Part 4a: Wait at Your Own Peril
Rebuilding a Dynasty League Roster, Part 5: The Free Agents
Rebuilding a Dynasty League Roster, Part 6: The Re-Evaluation Stage
Rebuilding a Dynasty League Roster, Part 7: The Secondary Targets
Rebuilding a Dynasty League Roster, Part 8: The Waiting Game