Fantasy Baseball: After the draft...The Art of The Trade

Fantasy baseball leagues come in various formats, but success turns on two activities: drafting and trading.  You can find scads of posts, even entire magazines, that prepare you for the draft, so we will focus on The Art of The Trade.

After the draft is over, most leagues break out into three categories:  Contending, Remodeling, and Rebuilding teams. Drunk on the Heady Hop of Hope, before the first pitch of the season, the guys who are, unbeknownst to them, already in the lower two categories, can maintain the fantasy that they are in the Contending cohort.  “What fools these mortals be!” [Puck, Shakespeare]

Between the end of your draft and Opening Day, you have an opportunity to greatly improve your chances.  The Contenders, aka “Sharks,” will immediately be courting the guys, who don’t yet realize they are in Rebuilding mode, and picking them clean.

You should have decided before the draft, whether you will go “All Vet” mode, “All Prospects” mode, or the “Hybrid” mode; but, since you didn’t, now is the time to make that decision and trade accordingly.  Your competitors who do not have a plan will wind up with the guys who forgot the directions to the game.

Act quickly; the Sharks had a plan before the draft and are already engaged in a Trading Frenzy; they will eschew attacking the other Sharks and head straight for the weakest fish, the ones who did not have a plan for the draft.  [The Sharp Sharks are already talking deals with their chums, before leaving the drafting room.]

Besides moving quickly, your best chance of out-smarting the Sharks is to be a better trader, so let’s turn you into Bill Veeck (as in “wreck”), Frank Lane, Theo Epstein, Kevin Towers, or Billy Beane.

  1.  Lose the fantasy that you will “put one over on” the other owners.
  2. Assess the needs of their team and yours.
  3. Make a list of targets to get and players you are willing to trade.
  4. Forget about a “quantity for quality” trade.
  5. Send a written offer that analyses the needs of his team and suggests solutions.
  6. Trades are an iterative process; a series of compromises and counter offers.
  7. Post-trade positive reinforcement.

Now on to the devilish details…

  1. Lose the fantasy that you will “put one over on” the other owners.

Let the ego driven Sharks try to rip off the other guys by stealing top prospects for aging veterans; the sharp ones will never trade the prospects that they drafted.  You may be dismayed to discover a Shark has pulled of Grand Theft Auto on another owner, but, remember, this is a long season and most Sharks will want to brag about how they picked the feathers off a gull and, once the gull figures it out, [or is told by another owner] they will not want to deal with the con man again.

Play for the long haul; establish trust; develop a reputation for being fair in trades.

2. Assess the needs of their team and yours.

Too many guys know what they need for their team, but do not assess the needs of the other team.

Ask these questions about BOTH teams:

Where are the holes at certain positions?

                Does he need a back-up catcher?  An INF UT player? Closer? DH?

Where are the holes in certain categories?

Pitching: Ws, ERA, WHIP, Ks

Saves: usually over-weighted as its own category.

Hitting: BA, HRs, SLG%, RBIs, Rs

Steals:  Stolen Bases, usually over-weighted as its own category.

[NOTE: Very few leagues will offer points for defense, so ignore Fld % and errors.]

3.Make a list of targets to get and players you are willing to trade.

Review the other team’s roster to see if he has players that meet your position and category needs and make a list.

Review your team’s roster to see if you have players that meet his position and category needs and make a list.

Ask yourself:  If we swapped all the players on these two lists; would that be fair?

Most likely that miracle will not appear; so start trying to balance this “package deal” by removing players from both lists.

When you find a set of matches (5 for 5, 4-4, 3-3, 2-2, or one for one) that, taken in total, are a fair balance of talent, you are ready to make an offer.

[NOTE:  It is easier to trade for even numbers.  Guys will propose “blockbuster” 5 for 1 deals and wonder why they are turned down.  The problem is that the guy getting the 5 players will have to drop 4 others from his roster to make room and the incoming guys may not be better than the ones already on the roster.]

4. Forget about a “quantity for quality” trade.

Remember the story of Jack and the Beanstalk?  It was a nice story, but it was a FAIRY TALE !

Don’t expect any owner to trade his cow for a handful [even a ton] of beans.  You will know when a Shark is attacking you, when he offers you “prospects” for a star player.  Also, unless you need to fill two or three holes in your position chart or your category chart, don’t swap a solid player for two mediocre guys.  You will fill the holes, but you will also need to drop a player to make room on your roster with the 1 for 2 deal.  Experienced fantasy players are leery of any “quantity for quality” offers.  Stick to the even up deals.  Once you turn down one of these deals, the Sharks will move you up a notch in their ranking system and move on to another owner.

5. Send a written offer that analyses the needs of his team and suggest solutions.

Trade conversations on the phone can get sidetracked easily and lose focus.  Also, there is the danger of escalating to an argument, when the tone or volume of the conversation shifts.

To keep the trade focused and unemotional, send the guy an email.  But, do not just send him two lists of players!  The art of the trade involves civility and thoughtfulness; you need to show him that you took the needs of his team into consideration, before crafting the list of players that you want.

Something like:

Hi Bob,

I took a look at your roster and compared it to mine.  I need a base-stealer and a back-up catcher and it looks like you could maybe use a power OF and an INF UT guy.

I noticed you have three guys who can steal some bases, [NAME], [NAME], and [NAME]  and three catchers [one of your catchers doesn’t catch much anymore; [NAME] is mostly a DH, but qualifies as a C in this league.  To address your needs for an OF with some power, I have [NAME} and [NAME] and I could offer [NAME] and [NAME] as possible guys to fit your INF UT slot.

It you think we can match up a 2 or 2 [or even 1 for 1] deal with some of these guy, PLMK.  Please let me know either way.

Thanks for considering.


So, you have sent a polite and thoughtful offer to another team owner.  If the other guy sees that your analysis of his needs is accurate and the players that you have to offer will be a good fit, he will review his roster to see which of the players you want work for him. This makes it very likely you will get back a more specific offer involving the players that you listed from both sides.

You have specifically requested that he get back to you, whether he likes your offer or not; that way, you are not left waiting for a “no thanks” reply, while you could be offering your players in other deals.

NOTE:  Any time you receive and offer or counter-offer you MUST reply as soon as you can.  He may have the players you want included in proposal with another team, so you want to be the first to reply!

Even if the guy sends you an initial offer that is totally ridiculous, don’t get insulted and write back: “Are you fracking kidding me?”  And, don’t you write something similarly insulting! Simply say, “Thanks for the offer, but I do not think we have the ingredients, at this time, to make a deal.  I look forward to future offers.” A single rude or insulting email to a guy will burn your trading bridge for the season and that guy will inevitably have the one player that you desperately need later on.

6. Trades are an iterative process; a series of compromises and counter offers.

If the guy sends you a reply with a counter offer, do not dismiss it immediately; review it and come up with a polite counter-offer.

“Gee, I really need to keep [NAME], since [NAME] has a history of injuries, but I could put [NAME] in the deal, who would address your need for [Position or Category].  I will look forward to your reply or counter offer.”   

Don’t get locked into your initial offer in a “take it or leave it” attitude; you may find that throwing names and matches back and forth will result in something you had not considered possible.  Stay open-minded, flexible and cordial. Keep the ball going back and forth in a deal as long as possible.

Remember, the easiest deals are even up ones: 1 for 1, 2 for 2, 3 for 3, in that order; the more players that are involved, the more complicated the deal and many guys are nervous about large deals.  Sometimes you can get a 1 for 1 done and then decide to add a player on each side.  If you sense that the guy is getting nervous about any more than a 1-1 deal, do not pressure him!  Just make the 1-1 deal and get it done.

If, after several counter offers, you do not see a deal happening, suggest that you need to “think about it” and you will get back to him by [tonight, tomorrow], so he is not left hanging.  Then, in your reply say:  “Thanks for putting in the time to make an effort to craft a fair deal. I do not think we have the ingredients, at this time, to make a deal.  I look forward to future offers.” REMEMBER: A single rude or insulting email to a guy will burn your trading bridge for the season and that guy will inevitably have the one player that you desperately need later on.

7. Post-trade reinforcement

In the email to conclude a deal, don’t just list the players; include a review of what were his needs and your needs and describe how the players he is getting fit his team.  Mention that you are glad that you worked out a deal that was balanced and fair and will be a “win-win” for both teams.

As the season progresses, if you notice that one of the players that you traded away does well, right after you kick yourself, send a short email to the guy who got your player:  “Hey, glad to see that [NAME] is doing well for your team!  Looking forward to working out more deals in the future!”

It’s called positive reinforcement; you remind him that dealing with you is beneficial to him and he will be much more likely to work out deals with you as the season progresses.

Final word of advice: don’t get so emotionally attached to your fantasy team that it ruins your appreciation of the real game and all its marvelous players.

“It’s just a fantasy; it’s not the real thing.” [Billy Joel]


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