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Dynasty Baseball Offseason Prep: Step 3 – Trading

Dynasty baseball hot stove season has seen big signings like Shohei Ohtani and Yoshinobu Yamamoto.  J15 International signees will ‘officially’ don their new MLB team’s cap in mere days.  Here in this series of articles, we have taken the first two steps toward an effective offseason: assess last year and scout the draft pool.  With Opening Day under three months away, we are about halfway through the fantasy offseason. Now is as good a time as any to consider how trading can be a part of your offseason program.  Every dynasty baseball league is unique.  In some, there is practically a trade per day.  In others, managers are reluctant to trade.  I have seen trends are consistent over leagues and over time.  What is the best way to make trades to help prepare for the 2024 dynasty baseball season?

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Dynasty Baseball Offseason Prep: Step 3 – Trade

When do draft picks peak in value?

I like to watch the way dynasty leagues cycle through the year.  In-season, we look at players doing well, adjust for injuries, and buy low or sell high depending on our team’s performance.  In the offseason, little changes with the talent of actual players but we have lots of time to research.

In my leagues, it is difficult to convince others to trade in the fall.  People burn out on fantasy baseball or move on to other fantasy sports as the weather gets cold.  Managers also want to wait to make big moves until they have analyzed last year.  Perhaps they even want to listen to podcasts and or see projections for the coming year.  No one wants to trade away a guy in October who shoots up the ADP charts in March.

Reluctance to trade changes by rookie draft day.  If you have read this series so far, you have made a general plan for where you want to get this offseason.  You have looked at the player pool for the draft and what your picks might reasonably net.  Between now and draft day, draft picks are going to hit their peak price.  People love to make picks – myself included.  Managers fall in love with the players available with those picks.  Trading can happen any time, but if you are selling picks the best time to get a premium is between now and when you are on the clock.

Usually, the market for crusty veterans is best in July and August, when what matters most to contenders is the stretch run.  Not always.  There are often a couple of managers who either do not value prospects or procrastinate in their preparation and are willing to move out picks for solid veterans year-round.  Keep up relationships with your league-mates.  Learn who cares about prospect drafts –  someone usually does not.

When to trade a draft pick

From one perspective, if you use a pick on a player whose value increases beyond his draft position, you win.  If you use a pick on someone whose value declines, you lose.  League context matters.  If you are in a league where prospect trades are rare, and thus you will never be able to trade them, you lose on every pick who does not end up contributing to your pro team.  If you are in a league with prospect hounds who want every hot prospect, open your mind to prospect arbitrage.

Whatever you think of a player in a rookie draft, you need to admit you are probably off, maybe by a lot.   I have found picks for future drafts and older, established prospects are slightly devalued while this year’s picks come at a premium.  Today, those top rookie picks feel like guaranteed stars.  Many of those first-rounders will lose a lot of value by this time next year.  Factor that in.

You can always trade picks for pros.  In many of my leagues, teams need to cut down their offseason rosters before opening day (even in pure dynasty leagues).  Most competitors in those formats would love to net a pick for someone they might have to cut anyway.  The ‘smart’ play prior to a draft with prospect fanatics is often to trade away picks  But trade the picks for what?

From another perspective, just because you cannot guarantee success in the prospect draft is no reason to avoid it. There is a downside to tossing away picks to the piranhas one by one.  If you miss on several prospects but hit big on one or two, that might be enough.  If you value Wyatt Langford highly, for example, it does not make sense to trade a pick where you could get him just because you can get a lot back.  Getting a young potential all-star player is the ultimate target.  You will eventually need to find a star in the draft.  Established players with star potential do not come cheaply.

Pick quantity > pick quality

Redraft fantasy leaguers profit from ADP.  Tens or hundreds of drafts based on pro performance and reasonable expectations for the coming year produce wisdom of crowds.  For dynasty football players, the NFL draft gives strong clues as to the immediate opportunity for incoming rookies.  Dynasty baseball prospect drafts cannot fully anticipate future performance or opportunity.  The development curve for baseball players is too long and unpredictable.  Beyond the very top picks, the odds are the order in which players will be selected will not at all resemble their ultimate fantasy value.

When you can’t trust the consensus No. 20 pick is better than the consensus No. 30 pick, it becomes reasonable to trade #20 for #30 and #40.   I got Jackson Chourio in the 5th round in two different 16-team rookie drafts over the years.  This was not clairvoyance.  I just had a lot of picks and could afford to take chances.  Good things happen when you get more bites at the draft apple.

Park factor arbitrage

Experienced dynasty prospectors know a few factors that can cause trading inefficiencies.  One is to leverage extreme minor league park environments.  The best hitters’ parks will juice offensive numbers and punish pitchers.  The best pitchers’ parks, however, do the opposite.  Keep in mind these are only home park factors relative to these players’ leagues.  Thus what may be a tough scoring environment in one league might be average at another level.  While this  concept may not be news to you, it is worth seeing trends on the most extreme parks of 2023:

  • Top hitters parks in 2023 included Charlotte (CWS-AAA), Albuquerque (COL-AAA), Reading (PHI-AA), Amarillo (ARI-AA), Lansing (OAK-A+), Asheville (HOU-A+), Stockton (OAK-A), Lakeland (DET-A).
  • Top pitchers parks in 2023 included Sugar Land (HOU-AAA), Akron (CLE-AA), Binghamton (NYM-AA), Mississippi (ATL-AA), Arkansas (SEA-AA), San Antonio (SD-AA), Beloit (MIA-A+), Fort Wayne (SD-A+), Tri-Cities (LAA-A+), Modesto (SEA-A), Fort Myers (MIN-A).

So what have we learned?

Now that you have scouted your prospects, you can sell or hoard picks with a sense of the direction pick prices will go.  Identify the non-pick assets you can get for picks.  If you play the prospect-picking game, trading down for more shots is my recommended strategy.  And if you are looking to make a trade involving established prospects, be aware of the most important park factors that may distort player performance.  Next time we will talk about prospect draft day.

Jesse is the host of the podcast Dynasty Sports Life, covering Dynasty Baseball, Football, Basketball, and multi-sport leagues.  He also co-hosts the podcast Fantasy Hockey Life, focusing on Dynasty Hockey.

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