Building A Winner In Dynasty Leagues: The Lifshitz Pillars Of Success

Photo courtesy of Bryan Green

“There is no limit to your insanity, you know that, right?” She says as she looks at me with a mix of aggravation and amusement. I just smile as I always do, shrug, and make some Wu-Tang inspired Kung-Fu reference about sharpening my sword. We’re just a few days into the offseason and I’ve already participated in my first Mock Draft. The 2Early Mock run by Fantasy Maestro extraordinaire Justin Mason, but that however was not the reason for my wife’s aggravation, it was instead my decision to join yet another dynasty league.

Including this new endeavor I’m up to an astounding 14 leagues. My goal was to cut down to about six this off-season, and while I have a couple of for sure cuts, I’m still going to be maxed out. Nevertheless I persisted, the draft started on a Monday in November. A classic slow draft style, customary for leagues of this size and depth.

 In my years playing in dynasty leagues there’s a few lessons I’ve learned over time, lessons I believe to be paramount to success. Unfortunately I’m still learning a few myself. I ain’t perfect!

Here’s a quick run down of the Lifshitz Dynasty Pillars. By the way, just because I’m an actual idiot, I’ll share with you times I’ve broken these rules.

1. Read the Rules: This seems like some dumbass ish right? Of course you should read the rules, but have you? Have you read the rules to the point that you understand them? Formulating your strategy is heavily dependent upon knowing the ins and outs of the rules, scoring, and the process of player acquisition in your league. If you know the rules, it will make defining your strategy that much easier.

Time I Broke this Rule: RDI last season. I 100 percent didn’t understand the impact of giving up keeper spots for initial draft slots in the startup draft. I kept all of mine and decided to draft late, with what I though would be the advantage of keeping all 35 of my possible keeper spots. Honestly, I should have given up 5-6 spots for an upgrade from my draft slot of 19 out of 20. I glossed over the rules, while someone like Eddy put more thought into it, stole the top pick and is in a much better spot. Reading is essential! Just to hammer home this mistake, I had Eddy jump on an accompanying podcast (see above).

2. Formulate a plan, and stick to it: This should be a product of the first pillar/exercise. You’ve read the rules, you understand how the league works, and now you’re going to apply that knowledge to your draft plan. More on the type of approach you should consider in a minute. In the draft mentioned in our opening, it’s a salary cap dynasty league, so control and surplus value across the board is paramount. In a shallower dynasty with no salary cap implications, chasing prospects isn’t as important. You should value right now production significantly more.

Time I Broke This Rule: More of why I broke this rule below, but the best example I have is the Real Fake Dynasty put on by Paul Martin and Walter McMichael. I went had one foot in the major league pool and the other in the prospect pool. When you do that you end up with half of nothing. No half measures.

3. No Half Measures: This lesson likely will have some detractors, and if you’ve been successful going half majors and half prospects, you’re a better drafter than I... Or your league stinks. Anyway, why do I say no half measures? Because you’re at the mercy of both plans working out. The best way to proceed is decide before the draft whether you’re in it to win it the first 2-3 years or if you’re going to build.

In a salary cap league I’m more inclined to go full build as I want to control my costs in the first few years. This is beneficial because it allows me to attack free agency and over pay for veteran MLB players as my window opens. It also allows me to take on bigger contracts in-season from teams looking to add prospects. By going full prospects ghost ship, I have the best of trading commodities; 50 prospects with varying degrees of ability and opportunity ready to move in order to get a star MLB player on a bigger contract. A few years ago I moved a package of five prospects highlighted by Jorge Bonafacio (seriously), for Clayton Kershaw on a four-year, $30 million per season contract. Has Kershaw been worth that contract? No, not the last few years, but he helped me win in consecutive seasons, and flags fly forever, or something like that. The best part was my acquisition cost was more depth than talent. The other owner was going nowhere and just wanted to be rid of Kershaw’s contract. I had the cost control and asset to fit the best pitcher in the game (at the time) into my squad for three good years.

The other bonus to going full rebuild in any league is the higher draft picks you’ll receive the following off-season. Pretty good trades assets in and of themselves. So, not only do you have a team of ascending assets, you have higher value picks coming your way, both of which you can trade for upgrades. It’s a recipe for a quicker path to competing than many realize. It’s the half measure teams that will likely fall back to the pack, losing steam with each passing year, trading prospects to get right now production, or going the opposite way and selling vets for prospects. Either way you’re on tilt. Being on tilt is bad.

Time I Broke This Rule: I did this twice last off-season, I went half-measure in RDI and in Real Fake. Each of these teams is my least favorite of the bunch.

4. Don’t Overthink It: I do this constantly. I go in, know who I should take, it’s in my notes, the projections back it up, and then I get cute. I did this last year in RDI when I passed on the obvious pick of Jose Ramirez at 19th overall. Who did I draft instead… Gary Sanchez. For some reason I decided to fully zig, thinking I was out-smarting the room, and in the end I flipped this “rig” on it’s side. My doubts over the legitimacy of Jo-Ram’s power were unfounded, and I ended up with a catcher who hit below the Mendoza line when he wasn’t hurt. While a lesser man might hide from these mistakes I wear them like the rings of a pimp. Recognize your mistakes and learn from them, it’s the only way you’ll ever get better.

Time I broke This Rule: yeah, yeah, yeah, see above I drafted Gary Sanchez 19th overall dummy.

5. Do Your Homework: There’s nothing more important than doing your homework in dynasty league’s. That doesn’t mean that you need to know 700+ prospects deep waking out of bed to a bullhorn at 3 a.m. You just need to have a type of prospect you chase and keep your ear to the ground for fluctuations in value. That’s not saying you can ignore prospects completely, but it doesn’t have to be the focus of your team. I tend to draft younger teams as my strength is knowing the minor league player pool and identifying future MLB regulars the room is low on. That might not be your strength, you might be better at identifying undervalued MLB players, or be good at negotiating trades. If you’re joining a dynasty I’m willing to bet you’ve got at least a few years of experience playing in redraft leagues. So identify your strengths and keep that in mind throughout the season.

This is two fold, as identifying where you’re strong will help you identify where you’re weak. That’s the area where you should do your most homework. I think we call this overcompensating in the real world, but no one is forcing you to buy a truck with a Rancho lift kit, we’re just asking you to learn a little.

This is something you should keep in mind when trading too. Regardless of how well I think I know a player, I always review the player(s) I’m adding as well as those I’m dealing before agreeing to any deal. Sometimes a quick look at a Fangraphs page can change your pre-conceived notions. Long story short, do your homework and assume nothing. We can all learn more.

Time I Broke This Rule: Have to say I do my homework.

6. Be Shrewd But Calculating: This one is pretty simple, don’t be scared to do what is right for your team despite your feelings for a player. You might love that 17-year-old power hitter, or righty with the 95+ mph fastball, but he’s not going to help your team for half a decade. Depending upon your league size, depth, and scoring this can dictate the value of these young upside types. In your standard 12-16 team league with five to 10 minors slots, you’re always better leaving those types for the guy running the prospect ghost ships. That being said, there’s exceptions. I’ve owned both Juan Soto and Royce Lewis in formats that shallow, but it was clear to see the market valued these two differently than a Geraldo Perdomo. I was able to turn those players into win-now pieces in a 16-team league to make a run at the title. So in other words, be shrewd about your feelings, but calculating regarding those you release into the player pool. Always exhaust your trade options on players you’re on the fence about.

Time I Broke This Rule: I released Chris Paddack in an 18-team dynasty league late in 2017, in another league early I released Ronald Acuña Jr. early in May 2016 following an injury. I suspected I would be able to snatch both back. That was not the case.

7. Be A Good Trader, Never A Desperate Trader: I think it’s well documented, particularly in the above podcast, but I’m a difficult trading partner. Despite the needs of my team, almost to a fault, I avoid making trades out of desperation. I’m also not great about negotiating with managers that send low ball starting offers. Honestly, neither of those traits are hallmarks of winning. In fact they’re deterrents; but that being said, you have to be smart about the deals you make, and taking the time to negotiate the best value is important. This is why playing in too many leagues is a major challenge, trading is essential and you’ll need to mine and farm your league and league mates for the best deals over the course of the season and off-season. Trading well wins championships simple and plain. I’m not scared to admit I play in too many leagues (working on fixing that), take offense to low ball offers, and often don’t spend the time needed to negotiate the best value. I’m not perfect, and I strive to be a better player. Just like you.

Time I Broke This Rule: Too many times to count.

Conclusion: In the end, there are a lot of ways to win your league, and certainly my seven pillars to success are by no means the only way. But, I do believe if you follow these steps, you’ll be more successful than not, and will build not only for this season, but future seasons as well. Have fun and good luck! Remember we’re here to help.