When I decided on this week’s topic, I remembered the first piece I ever wrote was about trading. It was probably called, “Tricks of the Trade”, “Art of the Deal” or one of the plethora of puns that have been used to title similar discussions over the past 27 years. There is a good chance you’ve read one… or 18 of these pieces. Hopefully, I can offer you a unique take or two.

The biggest mistake when negotiating is needing to “win the deal”. The objective is to make your roster better and improve your chance of winning. How many times have you seen someone share both sides of a trade and ask, “Who wins?”

To be honest, it’s impossible to judge who wins, even if the talent looks wholly lopsided. Trades aren’t about the relative quality of the exchanged players. A swap is about the potential of your roster before and after the deal. Sometimes, it’s more than just the players involved in the deal. Who gets replaced is part of the analysis. Often, the deal generates roster flexibility so you can activate a player from reserve, minors or IL. This player wasn’t involved in the trade, but he’s part of the overall roster evaluation before and after the deal.

This isn’t relevant until much deeper into the season, but often seemingly imbalanced deals address a specific need in roto-scoring, usually stolen bases or saves. The singular nature of these categories is such that one player can make a big difference. Dealing away more “value” to gain places in the standings is a fair swap, even if it appears uneven to those considering just the principals in the deal.

There is another element to consider beyond accepting a deal which helps your team: Is there an available which can help even more? Personally, this is my biggest obstacle in the trading process. I get the guilts telling someone I’m taking a different offer. Yes, I know it should be treated like business and not personal, and my concern is almost always irrational. When I inform someone that I’m not accepting their offer, it’s not like they spend the rest of the day cursing me and perhaps casting a spell on my well-being. Yet, that’s how it feels to me. I envy those that can say “no,” and move on.

Let’s assume you’re normal and can deal with politely telling another human being you’re going in another direction. You need to solicit offers to reject. My personal rule of thumb is if you’re initiating the negotiation, “Make me an offer,” doesn’t suffice. Don’t expect me to do all the work. Discuss the framework of a deal. Mention a specific element of my roster so I know you’ve put some effort into it.

Something you’ve no doubt seen before is don’t just think about your team; make proposals that benefit both sides. This rolls back into the desire for many to win a deal. You need an asset I have. Can I afford to give it up? Asking me for a player for whom I clearly need is bad form, and sets a negative tone for a counteroffer, let alone future negotiations.

Along these lines, the best offers involve choices. Everyone likes to feel like they’re in charge. Proposing multiple options gives the other person the perception of being in charge, but you’re the one pulling the strings. The notion is you’re fine with everything you propose. “I’ll you Jones or Smith for Wilson or Adams.” It doesn’t matter who your trading partner selects; you’re good with the deal. On the flip side, they’re making the ultimate decision, so they feel like they’re in charge.

Another benefit from proposing choices is more often that you’d think, you end up acquiring the player you prefer and/or dealing away the guy you like the least. Had you proposed a one-for-one, it may be accepted, but you could have received a player you wanted more if you offered a choice.

Let’s stay on the subject of control. Many are put off by lowball offers. To be honest, in some instances, so am I. This is mostly in a long-standing established league where the team managers know each other. In newer leagues, or those with unfamiliar team managers, a lowball offer can be a cry for help. Some are not confident enough to extend a fair offer. Instead of being insulted and ignoring the team manager, try engaging them. There’s a good chance some league mates aren’t so gracious. It’s likely this person wants to make a deal. Others may come back with an equally ridiculous counter. Instead, respectfully decline, but keep the negotiations open. Reply with a general reason, then push the deal elsewhere. Something like, “Sorry, that’s not a direction I’m interested in. Is Lopez available?” If Lopez isn’t available, you may learn who is, and go from there.

While this isn’t true of everyone, many prefer smaller deals to multi-player proposals. Any time I’m offered more than two players, I ask which of my players you are really asking about, and we focus on that player or two. Most of the time, everyone else included, is done for balance. The person tabling the offer couldn’t land on something smaller they considered fair, so they add on to both sides until they derive what they perceive to be fair. It very well may be that I can’t come up with something smaller either, but I want to try.

I could go on, but let’s call it a day. Later in the season, we can broach the subject again, perhaps discussing trading in keeper and dynasty leagues. What are some of your trading tactics?