Win Your Fantasy League: 10 Tips For Making Better Trades

One of the best parts of fantasy baseball is trading. There is just something so satisfying about working out a deal that is both exciting and sometimes nerve wrecking.

But don’t be fooled, trading in fantasy baseball is not a crap shoot—it’s an art, and if you can become a good trader you're going to stand a lot better chance of finding your name at the top of the standings.

Here are ten tips to become a better fantasy baseball trader.

1. Patience Pays Off

Don’t get frustrated when the first deal you offer someone doesn’t go through, and don’t always assume you have to accept the first deal you’re offered just because your team needs help.

Sometimes it takes a lot of work to make a deal happen and that’s not a bad thing. I’ve spent a week or two going back and forth with people trying to work out just the right deal—your goal is to not settle and get the most out of a deal as possible.

If you are working with someone who is cooperative then feel free to take your time. When you get offered a deal let the other person know why you’re not accepting and who you like and don’t like in the deal and then make a counter offer. Chances are if they don’t like your counter they’ll at least have the courtesy to do the same as you and the more information on the table the easier it’ll be to work something out.

Just like in the big leagues, it doesn’t always happen right away. In fact, in my experience, I rarely have my first offer accepted or accept someone else’s for that matter. 

Shop Around

If you’re going to trade a big name player, don’t make it exclusive to one team.

I am in a 16-team league where my hitting is stacked and my pitching is mediocre. I tried trading Carl Crawford, A-Rod, and Mark Teixeira and wasn’t getting good value back. I had Hanley, but didn’t want to trade him.

I got an intriguing offer and realized I might have to move Hanley. Instead of taking that offer without any other considerations I sent out a league wide e-mail letting everyone know that I was willing to move Hanley and what I wanted to get in return (which brought out more offers).

Ultimately, the original guy came through with the best offer, but it was better than the first offer because he knew I was getting other offers and I was letting him know.

It's All About Value

It’s not about how you value someone but how the guy who has him does.

Just because you think Jayson Werth is a Top 10 outfielder doesn’t mean the guy who has him thinks so. We often pay what we think a guy is worth when the other guy may think he’s worth far less.

This goes with a tip that’ll come later, but feel the owner out on a guy and figure out what he thinks of the player you want and than offer the trade. You never, ever, want to give up more than what you have to.

Last year I wanted Cliff Lee and I sent a guy an e-mail asking what he’d want. He offered me Lee for Stephen Drew which I accepted in a heartbeat. I would have never thought to offer that, but he overvalued Drew and undervalued Lee and I came out the winner.

Start Low

Don’t start negotiations with your best offer. Start low and let the other guy counter to something more realistic, cause every once in a while your low ball offer will get accepted.

Everyone assumes that the first offer isn’t the best offer so chances are they're going to decline and counter for something better. Start low and then when you get to what you’re actually willing to give, the other guy will think he’s getting a good deal.

Just don’t go so low with your offers that no one wants to deal with you. Hardcore fantasy baseball players don’t want their intelligence insulted with horrid offers.

Choose Your Trading Partner Wisely

One of the keys to trading is finding just the right partner. There are two things you want to look for when choosing someone to trade with.

The first of them is their position in the standings. You’re going to have a lot more luck trading with someone who is struggling than the guy at the top of the league who is terrified of tweaking a team that is excelling. Take advantage of the guy who can’t get out of last place, he is much more likely to do something drastic to shake things up.

The second thing to do is find a team who needs what you have and are willing to give. If your trying to trade Adrian Beltre don’t shop him to the team who has Ryan Zimmerman, find the guy who has a platoon of Brandon Inge and Andy Laroche.

If someone needs a player badly enough, the value of your player goes up tremendously. Exploit that as much as you possibly can.

Sell It

Make your trade sound as appealing as possible. Find a way to rationalize the deal and give the other team a reason to accept. It’s up to you to convince them that what you’re giving them will help them get better, even if you don’t believe it.

I traded Ryan Ludwick for Elvis Andrus earlier this season and I sold Ludwick and the fact that he was in the same lineup as Holliday and Pujols. I made it sound like he was going to be a top 10 outfielder.

Apparently my sell job worked. Again, it's not what you think, but what they think. Your job is to influence their thinking.

Know Your Team

While you have to consider a player’s value to another team, you also have to be aware of their value to your team.

If you can only play three OF’s and you have three guys better than someone like Bobby Abreu, than Abreu doesn’t have as much value. You should try and move him for as much as you can get, but ultimately getting someone who you are going to play is going to be more valuable than Abreu is on the bench.

Know Your Standings

This is staying with the theme of know your team, and with that, you have to know your standings. You should be checking the standings on a regular basis and staying aware of what exactly your team needs in the way of stat categories and what you can afford to lose.

One of the best fantasy baseball tips I have ever gotten was that it doesn’t matter if you win a category by one or 100. You don’t get bonus points for having 100 more homeruns than anyone else does.

This applies more around the end of June when you know what categories you are running away with and which one you might have no chance to catch up in. If you are not going to catch anyone in saves and you have that one closer, trade him.

Right around the end of June you need to make note of which categories you can still realistically make up a lot of ground in and aim to get better there. Right now you have a chance by keeping an eye on things to hopefully avoid getting taken out of the running in a category.

More often than not the teams who win the leagues I am in are the teams who are well balanced and scoring in every category.

Keep Your Poker Face On

The team you are trading with doesn’t need to know how much you like the guy you are getting or how much you dislike the guy you are trading away. This is part of selling a trade—convincing the other guy you either do or don’t value a particular player in a way that he or she does.

If a guy sends me an offer and says, "I absolutely love Choo, what do you want for him," I have a big smile on my face because I instantly know I can take advantage of this guy.

Don’t tell the guy who has the player you want that you love him—always undersell and even when you get an offer you like, try and get more.

Trade With a Purpose

I love making trades just as much as the next guy. I can literally spend hours out of my night trying to formulate the perfect trade scenarios in my leagues if I let myself—but the point of trading is not because you’re bored with your team or because you just need to do something.

The point is to make your team better. You’re not going to win every single trade you make, but don’t be the guy in the league who will make a trade just for the sake of making a trade.

Instead figure out who that guy is—and take advantage.

What does everyone else think about all of this? Feel free to add any tips of your own or perhaps you have an example of a trade that implements one of these principles. Let’s hear what you think about trading. If you have any trades on the table right now feel free to throw them up on here and I’ll try and give you some advice.

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