Dynasty 101: Know Your Window

Why is the middle so bad in a dynasty league and how do you get out?

I am a firm believer that the primary goal of playing fantasy baseball is to have fun. Dynasty baseball leagues in particular can offer a genuine sense of community and connection with people you might never have the opportunity to connect with otherwise. A huge “fun factor” in dynasty leagues is also building a team you are proud to put your name on. For me, there are two outcomes I want to strive for each year: first place, or last place. In-between that is a place where dynasty teams go to die.

Mediocrity… Truly one of the worst things you can achieve in a Dynasty Baseball league. If you have played in a dynasty league for any length of time, then I am sure you have encountered someone who always seems to place in the middle of the pack at year’s end. While this might not be the worst thing in the world in a re-draft setting, in a dynasty, this is the equivalent of getting put in the relational “friend zone.” Nobody wants that outcome, and yet so many end up in that position year after year.

This begs the question: how do you know you are stuck, and what course of action should you take to move forward?

Don’t Be Like Larry

In one of my long-time dynasty home-leagues there was a guy, who for years, just couldn’t get over the hump and place in the money. Let’s call this guy Larry (sorry to all the Larry’s out there!) Every year without fail, Larry would work tirelessly at the draft and the trade table to assemble a squad of players in order to achieve the league crown. He would be all over the league chat constantly announcing that he would be yanking players on and off the trade block. His strategy to make up ground in categories would fluctuate wildly. One minute he would decimate his farm system by trading all of his youth for vets, only to begin moving them slowly to restock the farm for whichever prospect was garnering the most buzz. 

Honestly, Larry’s knowledge of the game and overall player base was second to none. The problem was he never formulated a plan and stuck with it. Let this be a cautionary tale as we plunge into some of the strategies and tell-tale ways to avoid ending up with a similar fate as Larry. If you make a plan and put forth the effort, the odds of you getting stuck in Larry’s purgatory of mediocrity will drastically decrease.

Deciphering Where You Stand

Now that we have established a middle of the pack finish is not a desirable outcome, how do you determine that’s where you may be headed? Once you have determined this, what plan of action should you take to shift gears and either tackle a rebuild or go for broke? You really have to know your window, and then pursue it.

One of the biggest mistakes I see people make is entering the season without a full understanding of their team in context with the rest of the league. The offseason in dynasty formats is crucial to getting the lay of the land and formulating your strategy. You have the advantage of being able to look at the previous season and literally take note of how many home runs it took to place in the top point scorers in your league. Compare that finding to your lineup home run projection, and you now have a better idea what you might need to target, or even better, what you might have an excess of.  

The nerd in me enjoys creating a spreadsheet or inputting my team into an existing software to compare my projections against my league mates, and although it takes some time, it really is worth it. Once you have a better grasp on where you stand in relation to the rest of your league, you can determine more accurately if the top is within your sights.

Time to Rebuild

Anyone who has ever played a franchise mode in a video game fully understands the allure of watching players go from potential dart throwers to superstars. This is what makes dynasty baseball so fun, but also so dangerous. If you don’t have a plan, then you will get caught chasing the metaphorical “white whale” of having that next superstar. I am in no way saying building your team around first round talents is bad, but setting an expectation to have a roster full of them will get you into trouble. This type of mentality will lead you towards weighing potential too heavily. This is why you make a plan, and you stick to it.

So, what does it mean to make a plan? For starters, once you decide you are going all-in on a rebuild, there can be no turning back. Depending on your league size, this likely means you must be content to place at the bottom of the league standings for anywhere from 1-3 years. This realization can be a hard pill to swallow, particularly if you view it as “donating” money to the league. This couldn’t be further from the truth if you are able to get your rebuild right. I like to adhere to a three-year plan, as it provides flexibility.

The Three-Year Plan

Year One: A New Hope

This will be one of the longer sections, because it is imperative to get that first year of a rebuild right.

First things first, make an account of all of your players through the lens of who will be contributing to a starting lineup three years from now. While players like Paul Goldschmidt or Max Scherzer are still very valuable contributors this season, the chances that they will be able to help you in a few years are slim. These are guys you need to move for future draft pick capital or young MLB players or prospects with upside.

Here’s the thing though, and I can’t stress this enough: shop your guys around. Just because you should trade your older players in order to stockpile young talent doesn’t mean you have to take the first deal that comes your way. Do the work, get the deal you want, and be patient! Remember, you have committed to a rebuild and have the luxury of time. 

My preference in a rebuild is to lean more heavily on the hitting side of young players, especially in my farm system. In fact, in one dynasty league I had space for 25 prospects in my minors and I chose to make 21 of them hitters at one point. The reason for this is simply that hitters are easier to hit on. They gain value much more quickly, and are easier to trade as you are entering your contention window.

There is one final thing to keep in the back of your mind as you lay the groundwork for your rebuild in your first season: don’t completely neglect MLB or veteran players. I know this might sound contradictory as I just told you to shop guys around like crazy, but you can’t expect to win if your entire roster is comprised of 18-21 year-olds. Be smart; investing in players right on the cusp of their prime could pay dividends when you enter contention.

Finishing towards the bottom of the standings is of utmost importance until you are ready to contend. This should be easy if most of your team are young players and prospects who don’t add a lot of big league value just yet. Your pride might take a little hit, but I promise it’s all worth it when you have the opportunity to select higher value players in the draft heading into year two.

Year Two: Patience Pays

By most accounts, the second year of a rebuild can be the most difficult. At this point, your competitive spirit is going to start nagging at the back of your brain like crazy. Some of the young players you have invested in during your Year One purge will have gained significant value, and the temptation will be to move them in a flurry of trades and push your chips in. As best you can, you need to keep the future in mind and build a competitive window that will last.

The Rookie Draft (or First Year Player Draft) heading into this year is going to add a huge influx of value to your team. If things went according to plan in year one, then you should have a top selection in the draft and possibly more draft picks to play with as well. Your first couple of picks will be easier decisions, but where dynasty teams are built is in the savvy selections in the later rounds. Use all of your picks to your advantage, do your homework, and make sure to go into the draft with a strategy.

All of this isn’t an excuse to sit back and just hope your team magically turns into a force to be reckoned with. If you are able to remain diligent, churn the bottom parts of your roster, and possibly capitalize on buying an injured player or two on the cheap, then you should be setting yourself up nicely for the final year. 

Year Three: Time to Fly

To quote the great philosopher Snoop Dogg from MTV Cribs, “This is where the magic happens.”

I love the third year, because at this point you should have more trade ammunition and upside plays on your team than you know what to do with. You should also have a dearth of young players who have become full-time regulars or are on their way to the big leagues. At this juncture, you will be faced with many more opportunities and the time to start making moves to supplement your young core will be fast-approaching. My plan entering the third year is never to sell the farm and just go for the championship. The phrase “Flags Fly Forever” is true, but not if it comes at the expense of building a true dynasty team.

Be decisive and calculating; don’t be impulsive and short-sighted.

All of this time, all of the research, all of the trades and waiver-wire pickups have culminated to where you are now. There is a very real possibility that your team could be in contention right now, but make sure that you look at the landscape of your league before making any earth-shattering moves. Upward momentum is a good thing. If I can place in or near contention, that tells me that my team is becoming a force to be reckoned with. This means the rebuild has been a success.

Hopefully if things fall your way, the team you have assembled will have a good chance of being in contention for years to come.

Gabe Zammit

Gabe Zammit has been writing about baseball since 2017. He is a contributor on Pitcher List in addition to Friends with Fantasy Benefits. Outside of the baseball world, Gabe is a music director and producer and loves to chat about anything and everything music.

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