If you’re anything like me, trading can sometimes be a scary proposition, especially if your team is shaping up to be a contender. Nothing is worse than an ill-advised trade initiating a team’s downward spiral when maintaining the status quo of players would have been the better option.

As unpleasant as the outcome of a trade can be, equally as displeasing is the feeling of discomfort during negotiations.  I’m sure you’ve felt before the pressure to respond decisively to an offer and maybe even formulate a logical counter of your own when really you just want to avoid making any drastic decisions.

So, that’s what I’m here to help with today—to make the trading process a bit easier. Beyond concerns of personal comfort, gaining confidence in trade negotiations can also pay dividends in the standings. Here’s are some tips to help you build it:

Join a league you aren’t fully invested in.

A common cause of people shying away from the trade market in a league is due to the league itself intimidating them. Similar to sitting down at a poker table with blinds above your bankroll, for a fantasy league, maybe there was a high entrance fee or a lot of prestige associated with it. Either way, you have to think twice before making any move. An easy way to get past that is to simply also be in a league you aren’t nearly as invested in.

For me, that league is the Razzball Experts league this year. I certainly care about my performance in the league (currently third), but it’s a relaxed 12-team mixer with standard settings I find comfortable. Last week, I was approached by Razzball’s Grey Albright, who proposed trading his Shin-Soo Choo for my Adrian Beltre. I wasn’t going to do that straight up, but given my glut of third basemen (Pablo Sandoval and Brett Lawrie), I was open to the deal. We went back and forth a few times with different versions of the trade, and eventually he accepted my proposal of Beltre and Josh Willingham for Choo and Jed Lowrie. It was a bit of a wacky offer, loaded with risk on my end and certainly not one I would have the guts to make in a more intimidating league. It’s too early for a verdict, but so far it’s worked out well, given Willingham’s struggles.

The point, though, is that engaging in such relaxed negotiations could help me in analyzing and countering trade offers in another league. Luckily, I don’t own Willingham anywhere else, but perhaps instead of frighteningly holding onto him, I’d be more cognizant of what I’d be willing to accept in return for trading his services.

Stay active on the trade front.

People who are legitimately afraid of trading don’t want to hear this, but it’s the truth. When you’re afraid of public speaking, the best way to overcome that is to just get up there and speak in front of people as many times as possible. Same with trading; the more you do it, the more comfortable you’ll become.

Perhaps you’re the sensitive type who might even feel a twinge of guilt when rejecting another owner’s offer, because even though you can tell he put a lot of thought into it, you just don’t know what to do other than hit reject. Straight rejection seems a bit too harsh, so at least you send him a little note back saying it was a fair offer but you just can’t do it at the moment. The fantasy baseball equivalent of “It’s not you, it’s me.”

The more active you are in discussing trades with other members of your league, the easier it is to reject each individual offer, since it doesn’t mean as much. You’re putting the requisite amount of time and effort into the league. Maybe I’m just ridiculously empathetic and the only person who has ever considered such things, but the less you have to evaluate the emotional aspect of a trade and can focus on the players, the better. That’s what Professor Micky Rosa taught me.

Know what you want.

This is fairly common trading advice, to have a clear idea of what you want from a trade. This trite expression is sometimes easier said than done, since often trades aren’t tidy little one-for-one swaps where each owner has a clear need met. It implies that you shouldn’t hesitate to reject any deal that doesn’t satisfy your explicit demands, but that also goes against most people’s trading ideal of being willing to accept almost any deal that you think will have a positive expected value.

Personally, I think you have to almost choose what kind of trader you are. Either you only make deals with clear needs met, often smooth one-for-one transactions, or you are the type of owner who has a price for everyone. Any player is available for the right package.

It’s harder to be the latter of the two, but the more active you are in leagues and the more leagues you’re in, the easier it is to gain the perspective required to pull it off. My advice is to be willing to accept being the person who only trades when a need is obvious, or for a specific man-crush, if you aren’t the most active fantasy baseball player (and yet somehow are still reading this).

So, now it’s your turn. Go out there and make a trade! Feel empowered! And, if necessary, the other BP fantasy writers and I are always around by email and on Twitter to respond to your proposed deals.

Thank you for reading

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Thank you for this. Good advice for us "sensitive types".
Thanks. It can be hard to keep a serious tone writing about this but I figured at least one person would relate.
Good article, one thing I struggle with is putting together offers reasonable offers. In anything beyond a one for one deal, any thoughts on making an offer that yields a counter offer rather than a flat out rejection and derision would help. I'm often hesitant to send out feelers lest I be characterized as unserious, even when those feelers are more to signal I'm interested in acquiring a player than an actual proposal.
If you don't want to make a direct offer, most league websites have a "Trade Bait" board where you can list the players you are willing to trade and then put in what type of players you're requesting. (i.e. "I need a power hitting outfielder and I'm willing to trade one of my closers.")
If you're interested in beginning a discussion rather than a proposal to start, then send an email or add comments to the feeler offer to let the other owner know your intentions.

Also, it helps to make an actual offer or at least try to identify the opposing team owner's needs and begin the discussion that way.
This sounds like common sense, but people should shut up with the whole "trade rape" thing. Ripping people who made a "bad trade" just shuts people down. Trading is only intimidating if people act like asses. Creating and promoting a positive atmosphere makes this more fun and more active.

That sounds touchy feely but whatever. There's only one rule that I know of, babies - god damn it, you've gotta be kind.