

The Art of Draft Pick Trading
I am engaged in a war. Not a real one, of course, but rather a battle for supremacy in the fine discipline of fantasy baseball. Born on the Fantasy Life App, the “Fantasy Life Dynasty” league is a ten team, H2H scoring, startup dynasty fantasy baseball league. In a future article I will analyze our draft, but this column will serve to discuss the preparation for that draft — more specifically, the draft picks I traded, and also my mindset behind each exchange.
As described in the title, draft pick trading (DPT) is an art. I set out to create the best foundation for a team that would last for years; my goal was to build a true dynasty. However, that sentiment is easier spoken than performed. I needed to complete five trades, setting in motion a master plan, in order to feel like I had succeeded, not only in improving my team, but also in creating the beginning of an empire.
Those five trades will be on display in this article, as I evaluate and share my reasoning for executing them, as well as discussing general DPT philosophies and fundamental ideas. Without further ado, let’s get into the trades!
TRADE #1
I traded:
1st Round Draft Pick (10th Overall)
2nd Round Draft Pick (11th Overall)
3rd Round Draft Pick (30th Overall)
4th Round Draft Pick (31st Overall)
5th Round Draft Pick (50th Overall)
6th Round Draft Pick (51st Overall)
8th Round Draft Pick (71st Overall)
10th Round Draft Pick (91st Overall)
12th Round Draft Pick (111th Overall)
I received:
1st Round Draft Pick (1st Overall)
2nd Round Draft Pick (20th Overall)
3rd Round Draft Pick (21st Overall)
4th Round Draft Pick (40th Overall)
5th Round Draft Pick (41st Overall)
7th Round Draft Pick (61st Overall)
11th Round Draft Pick (101st Overall)
13th Round Draft Pick (121st Overall)
16th Round Draft Pick (160th Overall)
Let’s examine all these numbers. I went into negotiations with one goal in mind: to get the #1 overall pick and secure the best player in baseball, Mike Trout. The first way to set about that goal was to understand the needs/wants of my potential trading partner; that step is crucial in every trade. After some discussion, I saw he was fascinated with the first/second round turn, and thus the talks began.
We reached a certain outline for the trade: We were going to swap a certain number of early round picks, and he would win by a fair margin on the back end of the trade, improving in multiple later rounds. We reached a point where he wanted to swap our 1st-4th round picks, then have me give my 6th and 8th rounders for his 7th and 9th rounders. However, one of my fundamental ideas set in: Higher round picks are far more valuable than those of lower rounds. Especially considering his 5th round selection was 5.01, I found it absolutely necessary to swap 5th round picks as well.
So, the conversation trudged on. I countered with an offer where I would obtain that more dramatic victory in the early rounds: We would swap 1st-5th round picks, and then I would give him my 6th, 8th, 10th, and 12th rounders for his 7th, 9th, 11th, and 13th rounders. I believed that the swap was almost fair, and that he could pick up important depth necessary for a dynasty league; he would gain a substantial victory in four later rounds. He didn’t go for it.
I knew that I needed to swap those early rounders to secure my advantage, but he wasn’t content with the back end production he was getting. After more discussion, we came to the completed deal: We would switch 1st-5th rounds, and then I would give him my 6th, 8th, 10th, and 12th rounders for his 7th, 11th, 13th, and 16th rounders (he wanted to pick twice in the 12th and have his 14th-15th stack, so I compromised, taking his 16th rounder).
I’ll be honest with you: If I lost a trade (and winners and losers can be quite blurry when one trades picks), it would be this one. However, another one of my fundamental ideas reminded me why I made the trade: I got what I wanted. If you set out with a goal of trading for a pick/player and you come away with it — without sending your team down the river — then from your perspective, you win the trade. Each side got what they wanted, so the exchange can only be considered a success. As for my team: I had my Trout, but there was still work to be done….
TRADE #2
I traded:
2nd Round Draft Pick (20th Overall)
3rd Round Draft Pick (21st Overall)
I received:
1st Round Draft Pick (6th Overall)
4th Round Draft Pick (35th Overall)
After feeling a bit insecure about the back end production I lost in the first trade, I quickly set out to complete another deal. After all, I didn’t feel like my team was ready to be drafted with the current picks I possessed. So I sought after another exchange, following another one of my DPT philosophies: A higher and lower pairing of even AND odd round picks is better than the two in between rounders (when rounds add up to the same number, and also as long as the picks are standard for that specific drafting slot). In this trade, the two rounds of the picks on each side added up (2+3 = 1+4), and each side received an even and odd round selection, so I was more than happy to scoop up the book-ending picks in exchange for my trading partner’s idea of “depth.”
However, this deal conflicted with a different trading philosophy: Trade for your needs. Did I need another first round selection, compromising still elite 2nd and 3rd round talent? No. But the final fundamental idea of this section trumps the aforementioned theory: Do not pass up a trade at an excellent price. My ideals stated that I was the definite winner of that trade, so I felt inclined to accept it. While I may have been moving away from what selections I’d like to have come draft day, I was definitely improving my overall picks. Now, to spread that advantage out and build my dynasty….
TRADE #3
I traded:
4th Round Draft Pick (35th Overall)
4th Round Draft Pick (40th Overall)
7th Round Draft Pick (61st Overall)
9th Round Draft Pick (90th Overall)
I received:
3rd Round Draft Pick (21st Overall)
5th Round Draft Pick (46th Overall)
7th Round Draft Pick (66th Overall)
9th Round Draft Pick (86th Overall)
My previous trade had left me barren of 2nd and 3rd round selections. Stocked with elite talent, but at a much cheaper price than that of a 1st round pick, I felt the need to recoup and improve on that area of the draft. So what did I do? I traded for the 21st overall selection that I had just traded away.
Let’s take a look at the trade in bits:
I traded:
4th Round Draft Pick (35th Overall)
4th Round Draft Pick (40th Overall)
I received:
3rd Round Draft Pick (21st Overall)
5th Round Draft Pick (46th Overall)
Here is another example of the “Book-ending Picks Philosophy.” The rounds added up, and I got the highest selection. Analyzing further, I received an even bigger advantage: I moved up fourteen spots while only moving down six. Especially in the very top part of the draft, accomplishing that feat is nothing short of a great success. 21st overall is practically a second round pick, and winning at the top end of the draft is an incredibly important ideal to follow. Finally, I even managed to give up my lower 5th round selection (5.06 instead of 5.01). This half of the trade was pure profit.
Part 2:
I traded:
7th Round Draft Pick (61st Overall)
9th Round Draft Pick (90th Overall)
I received:
7th Round Draft Pick (66th Overall)
9th Round Draft Pick (86th Overall)
Immediately you may notice that this part of the trade features me receiving the middle picks, rather than the book ends. Why would I break my own rule? There are two main reasons:
- Philosophies can only take you so far. It’s great to have your own ideas and strategies, but at some point your imaginary fantasy landscape will turn into a real league that needs tough decisions to be made. For example, if you decide you’re going to take a catcher early, but Posey and Schwarber are gone before you can take either of them, you’ll adjust your strategy in order to improve your team.
- I needed to contradict my theory because that’s what was required to get the job done. I wish I could always stand by all my outlooks, but compromises must be made in order to benefit one’s team. I was not going to lose a great deal because I forced myself to adhere to one idea.
In the end, the advantage at the top end of the trade was so great that being the meat of the sandwich in the bottom half of the deal was no problem at all. I completed the transaction and improved my team, and that’s all that one can hope for in a trade.
Taking a broader look at the selections, I had picks 1.01, 1.06, 3.01, and 5.01 headlining my draft. I was definitely moving in the right direction, but that unnecessary first round pick would need to be turned into vital depth….
TRADE #4
I traded:
1st Round Draft Pick (6th Overall)
5th Round Draft Pick (46th Overall)
7th Round Draft Pick (70th Overall)
I received:
2nd Round Draft Pick (12th Overall)
2nd Round Draft Pick (17th Overall)
9th Round Draft Pick (89th Overall)
In my opinion, this exchange was the perfect use for the extra first round pick. Making a good trade — even though I didn’t necessarily need its main component — paid off in the end. Let the 70th and 89th picks be as they may — it is a noticeable difference, but as always, I focus on the more important, the beginning of the draft.
Preparing for the draft, I decided that there were thirteen elite players (the top two tiers). I set Trout and Harper alone in tier one, and then clumped the other eleven into a second tier. Therefore, moving down from 6th to 12th overall didn’t hurt at all — and moving up from 46th to 17th overall was a magnificent jump. Creating an outline of a draft strategy allowed myself to obtain my best personalized picks at the very best price. Preparation is key.
My team was finally starting to come into form. Picks 1.01, 2.02, 2.07, 3.01, and 5.01 are excellent building blocks for a startup dynasty league. Still, there was one final tweak to be made….
TRADE #5
I traded:
3rd Round Draft Pick (21st Overall)
11th Round Draft Pick (110th Overall)
I received:
2nd Round Draft Pick (13th Overall)
14th Round Draft Pick (133rd Overall)
Remember those thirteen top tiered players I mentioned earlier? This trade guaranteed that I got three of them, and at a great price, too. Moving up eight spots at the very top of the draft to ensure elite talent while only dropping twenty-three spots — where far less skilled and consistent players were to be drafted — was the final quality move I needed to promise an excellent base for my dynasty. I was to be stacked at the top end of the draft, able to grab a surplus of premier talent, while still maintaining adequate depth to build my team through the rest of my selections. Here is a final mockup of the picks:


I hope you enjoyed and learned from this article, and also consider employing some of these philosophies and ideas in your own fantasy leagues. Stay tuned, as next column I will analyze the selections of the real draft and discuss how I used my newly acquired picks.
Until next time, follow me on the Fantasy Life App @cb and on Twitter @CBRetweet.