Fantasy Reflections: To Trade, or Not to Trade?

I am, by nature, a procrastinator. This has been true for 31 years and counting, and at this point I am reasonably confident that it will remain as such. Sometimes the universe is so courteous as to provide distractions without me seeking them out. The writing of this article was slightly delayed (albeit still ahead of deadline, of course, since you’re reading it) by one such benevolent intervention.

In addition to my work here and the Monday AMA over at r/fantasybaseball, I offer consultation on 1:1 basis. In this instance, a client is fretting about a potential trade that has been in the works for a couple weeks. He’s contending but with a pitching staff that could use a boost. We’ve worked through a few other ideas during these conversations, but the one we keep coming back to has been the same for most of that time. It’s a close call, one that's hard to blame him for being on the fence about.

The details of the deal aren’t important. (Also, I take fake baseball advice giver-taker confidentiality very seriously and working in healthcare research means I understand the importance of de-identifying data.) Managing my own teams, I’ve had plenty of my own experiences in this area, as have you and everyone else in your league. It can be difficult to make a decision when time is beginning to run short and the fate of your season hangs in the balance. But across the fantasy landscape, trade deadlines loom, and so make decisions you must. What do?

That Is The Question

Be Honest

Take a long, hard look at your roster and the standings. In your heart of hearts, how do you feel about what you see? Are you confident that as currently constructed, your team can make a run? Does the roster only need a few tweaks or a little reversion to the mean from those already on it? Or do you need to go nuclear? Seeing your situation with clear eyes is the first step toward committing to a concrete plan, even if that plan is to do nothing.

Be Realistic

We’re rapidly entering crunch time, which means nobody wants to deal with terrible unsolicited offers right now. Put yourself in the other guy’s shoes and ask yourself if you’d take the deal you’re offering. You should be making any and every offer in good faith. Some will still be rejected, and they might be laughed off; it happens. Player valuations can vary widely even amongst reasonable owners. You can improve your odds by looking closely at your counterpart’s roster and standings and tailoring your offer in a way that plausibly benefits them. You may not want to underline that too heavily in trade discussions, though, lest you risk sounding condescending. They likely already know where their team needs work.

Be Patient

“Sitting on my hands is what got me here in the first place!” you say, preparing to throw full wine bottles at your computer screens. That may well be true, but it’s too late to do anything about what’s already happened. Don’t make things worse by jumping at the first deal you can get. Be quick about making those decisions, but you shouldn’t be afraid to walk away or ask for more if you feel it’s warranted and you’ve followed the first two guidelines. Be cognizant of the deadline without letting it make you feel like you’re backed into a corner.

Be Bold

Not to cramp Gabe Kapler, the (first-place, nbd) Phillies, or Justin Timberlake's respective styles, but there is a fine line between boldness and stupidity. Sometimes you gotta swing for the fences, and those kinds of moves can often prove disastrous for your team. That’s the risk you take. Just be sure that the level of risk you’re assuming is reasonable considering the potential reward. If the cost-benefit analysis bears out something you’re comfortable with, don’t hesitate to pull the trigger.

Be Happy

I say this a lot, but it bears repeating: This is just a game. Sometimes bragging rights or monetary considerations are at stake, but mostly we’re doing this because we enjoy the experience. It’s easy to lose sight of that. Save the agonizing for decisions that really matter (insofar as anything matters), decide on a course of action for your fantasy squad, and make peace with however the chips fall.