The Art of the Deal

Long before he became the President of the United States, Donald Trump wrote a book called “The Art of the Deal.” I recall reading the book back in the 1990’s when I was desperately trying to make enough money in the financial services business to support my family. Sadly, the book didn’t change my life, but it was entertaining.

“Deals are my art form. Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals. That’s how I get my kicks,” Trump wrote. This resonated with me, and it still does. I like making deals in fantasy sports. The art of the deal in fantasy football (or baseball) is making a great trade.

Trading is an excellent way to strengthen your roster – even before the season starts. After the drafts are over, fantasy managers usually sit back. That’s not what I do. When my drafts were over on Sunday, I immediately started looking at ways to improve my teams. I have spent the last few days texting with other managers about trading.

In one league, I drafted Christian McCaffrey in the first round and then made a point of looking for Elijah Mitchell late as an insurance policy in case McCaffrey was injured. By the time I started looking for him in the 11th round, he was already off the board. I put out a feeler to see if his manger would be interested in trading Mitchell to me.

The manager told me he’d trade Mitchell, but the deal had to involve either James Cook, or Rachaad White. He also expressed an interest in Marvin Mims. There was no way I would have traded either of those running backs for Mitchell. But I countered with Cook, White and Mims for Josh Jacobs and Mitchell. He declined that offer.

This manager and I went back and forth but were unable to agree. The problem with trading is that we all value players differently, and I find that other managers value their players more highly than I value them. I consult trade value charts for a third-party opinion, and I would recommend you do the same. I like the one at CBS Sports.

Trading strategies vary, and trading philosophies differ. For instance, my son loves to buy low and sell high. You may wonder what’s unusual about that, but he takes it to an extreme. If I have a player that I think is a bust, Nathan may have a higher opinion of him than I. Sometimes, I can use this against him if I want to dump a player to cut my losses.

Every analyst seems to write about players you should buy low, or sell high. I read them all because you can find good information, but you should take all information with a grain of salt. There is also a time you should sell low. If I had drafted Cooper Kupp (I didn’t), I would be watching the news carefully to see if I should sell low on him.

When you trade, don’t get caught up in who “won” the trade. Everyone wants to win, but winning on a trade isn’t the name of the game. A trade can actually be a win-win if both teams are improved by the trade. That’s the objective of any trade – to make your team better. If you think that your lineup is stronger after the deal, then you made a good trade.

Sadly, I’ve found that most managers won’t trade because they fear they are not going to get a good deal. This is unfortunate because trading is fun, and it’s the best way to make your team better quickly. Six years ago, I picked up Alvin Kamara off the waiver wire and traded for Mark Ingram. I started both of them throughout the season and won the league.  

If you’re going to make a credible trade offer, find a trading partner who is weak at a position where you are strong – and vice versa. For instance, if I’m deep in running backs and weak in wide receivers, I am looking for a trading partner who’s weak in running backs and deep in wide receivers. Don’t just look at your team – look at his team, too.

If you’re new at trading, you may want to employ the KISS principle. KISS stands for “keep it simple and straightforward.” You may have heard another variation of this acronym: “Keep it simple, stupid.” A simple trade would be a straight up, one-for-one player trade. My experience is that the majority of trades in fantasy football are one-for-one deals.  

While one-for-one trades are the most common, multiple-player trades are more fun, and they offer a better chance to achieve the win-win objective. For instance, I knew I was going to have to give up something to get Jacobs. So, I offered the manager all three players he was interested in, hoping that he’d bite. He would have received three players for two.

If I receive a trade offer from another manager, I always counter. In another league, a manager offered me Deebo Samuel for Rhamondre Stevenson. I countered with Samuel for White (since he was long in wideouts and weak in running backs). He said no, so I offered Stevenson and White for Devante Adams. No dice, but you should be getting the idea.

There is an art to making a good deal in fantasy sports. But you have to be able to think outside the box and also see things from someone else’s perspective. Always try and find out what your trading partner wants and give him what he wants. Trade from a position of strength into a position of weakness, evaluating the risk and reward in every potential deal.

Thomas L. Seltzer, AKA Doubting Thomas, writes about baseball and football for CreativeSports. Be sure to follow Thomas on Twitter @ThomasLSeltzer1.

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