These 11 tips have helped me throughout my dynasty career, and I’m hoping you can find some value in them too. Here are the 11 Dynasty Baseball Rules to Live By:

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)