Over the course of the off-season I did a mini Dynasty Baseball Strategy Series on my twitter account (@DynastyHalp), and I wanted to collect them into one article. This builds off an article I wrote in 2019, 11 Dynasty Baseball Rules to Live By. Here is 10 (More) Dynasty Baseball Rules to Live By:

-Halp’s Dynasty Baseball Podcast: 2021 Top 100 Dynasty Baseball Prospects Rankings Series
-Top 1,000 2021 Dynasty Baseball Rankings
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1) Smart owners think ahead and start making strategic win now moves the year before they’re actually ready to compete. You want a solid group of vets waiting for your young core to breakout. If you wait too long, that is how you end up in never ending rebuilds.

2) Late career breakouts are the most underrated dynasty asset. How to profit from it it in 2021? Target Gio Urshela. BB% up 5% to 10.3, K% down 3.9% to 14.4%, and exit velocity up 0.8 MPH to 91.4 MPH. At worst he backed up his 2019 breakout and at best a monster 2021 is coming.

3) Be lightening quick to pick up “out of nowhere” young pitchers after 1 or 2 good MLB starts. Pitching development is especially non linear and so many studs bubble up from this group. deGrom, Bieber and Gallen most notably! If you hesitate, you’ll miss out

4) In leagues where you can pick up prospects whenever you want, you should be constantly trading prospects for win now pieces. Trust in your ability to pick up future breakout prospects for nothing off the wire. Churn and burn.

5) This article from 2019 is one of my favorite things I have ever written and what this tweet series is built off. Rule #11 seems very fitting in light of this past year: “This is supposed to be fun and take your mind off the more stressful aspects of life.”

6) Play with blinders on. When rebuilding the teams on top can seem unbeatable and discourage you from ramping up. Don’t let fear and intimidation beat you before you even try. Focus on your own roster and trust that cracks in the armor will emerge from the top dogs.

7) If your prospect and MLB drafts are separate, it’s best to lean upside in the prospect draft because opportunity for young proximity plays will be available in the MLB draft. High upside plays won’t be. If combined lean proximity early because there will be lots of high upside prospects available late.

8) Some teams are always on top cause they’re good at making trades that look lopsided at the time of the trade. Other teams are always on top cause they’re good at making trades that look lopsided a year or 2 after the trade. Don’t be the former. Be the latter.

9) In auction leagues, one of the best spots to find hidden value is by clearing cap space in offseason trades. There always seems to be this vague value put on it. Even if just a few dollars, it has the potential to sneakily swing trades in a major way if you use it wisely in the auction.

10) The time to trade prospects is when their hype and excitement is highest, which is also the time it will be hardest to part with them. Having a mind of your own and fighting against consensus on a guy you believe might be getting overhyped is how you profit.

Here is the original article from 2019:

1) Don’t be afraid to trade with anyone. I don’t care if they won the league three years in a row, or if after every trade there is a small peasant uprising about how unfair their trades are. Everybody is capable of being ripped off. In fact, the teams that are consistently at the top of the standings are the most ripe to be fleeced. They often have the most ego and most confidence in their evaluations. Pride cometh before the fall. Not only shouldn’t you avoid trading with them, you should target them. There is no faster way to catch up to those top teams than to be the one taking their underappreciated assets away from them. Be the team that profits from the value that is falling off the back of their overstuffed championship truck.

2) Don’t trade highly rated prospects if they struggle in their first and/or second season. Hold them. Target them from other teams. But whatever you do, do not trade them. You will not be able to come close to getting that upside returned to you in a trade.

3) Build with hitting. The worst teams in dynasty leagues are always littered with failed, injured, and/or bullpen’d pitching prospects. When your offense is ready, that is when you pour all of your resources into aces, closers, and low cost pitching sleepers.

4) Don’t be afraid to “lose trades.” Don’t worry about your obnoxious league mates who talk shit in the group email. It will make it all the more sweet when you finish above them. The decision to make a trade should be a strict calculation on whether your team is better off with those players or not. Value in a vacuum or where they rank on a general ranking is meaningless. This advice assumes you shopped the player around and you know this is your best offer. If you didn’t, then your obnoxious league mates are right.

5) What helps me get over the endowment effect (the hypothesis that people ascribe more value to things merely because they own them) is to imagine I already own the players that are being offered to me, and I’m trading for the ones on my team. It may sound silly, but when I flip trades around like that in my head, it can become very clear which side I prefer. Many times I will be on the fence about whether I should pull the trigger, and then I reverse it in my head, and realize it wouldn’t even be a question if I already owned the players being offered to me. That might have been a bit confusing, but I feel like you guys get it.

6) In roto leagues with no playoffs, don’t be afraid to go all in during the season if you see a legitimate path to a championship. Don’t get greedy and feel like you have a chance to win six championships in a row. Get your plastic trophy this year, and then rebuild. Rebuilding is fun, and is kinda the entire point of playing in dynasty leagues.

7) In playoff leagues, never go all in. Anything can happen in a one week playoff. It is all about getting in the tournament and letting the chips fall where they may.

8) Don’t ignore possible late career breakouts just because you are rebuilding. This also goes hand in hand with ignoring older, “low upside” prospects who should get playing time this season. So many breakouts have bubbled up from these groups of players in recent years, and it is usually the good teams, who are on the lookout for win now production, that scoop them. The rich get richer.

8a) Rule 8 also applies to making trades. I call these players “buy highs.” They are players who are producing unexpectedly well but nobody is fully buying into them. They will be included in many “sell high” articles, but these players make the best trade bargains. Nobody expects you to give up your very best prospects, and you can usually strike a very reasonable deal. Over the years, this strategy has landed me Lorenzo Cain, Max Muncy, Rich Hill, Charlie Morton, Jimmy Nelson, and many more.

9) In 30 team leagues, don’t overvalue superstars. It is all about depth. Which for better or worse is what real MLB teams are starting to figure out and act on.

10) Like any business or sales job, you are really selling yourself. You want people to want to trade with you. You don’t want people to hate you and hate dealing with you. Meaning don’t try to rip teams off, and don’t gloat about good deals. You are just poisoning your own well.

11) Don’t be afraid to take risks. Don’t be afraid to go with your gut. Have no regrets. This is supposed to be fun and take your mind off the more stressful aspects of life.

By Michael Halpern (@MichaelCHalpern)
Email: michaelhalpern@imaginarybrickwall.com
Twitter: Imaginary Brick Wall (@DynastyHalp)