Getting Started in a Keeper League

Getting started in keeper league fantasy baseball can be a challenge and inheriting an existing keeper league team can make even experienced redraft players feel like beginners again. Keeper leagues often have unique and arcane rules, and if you’re joining an existing league, you’re usually going to be handed a team roster that looks like a junkyard Yugo. How do you take a team of overpriced has-beens and turn it into a perennial contender?

Don’t panic. I’ve got your back. Over the next few weeks, I’m going to get you up to speed and ready for your first keeper season. Here are some simple rules to make sure you get off to the best start possible.

Don’t. Do. ANYTHING.

You’ve just joined the league, and the commissioner has introduced you to the other competitors. Within a day, you have half a dozen emails from your peers, all offering you bright and shiny new players in return for some of the bums you inherited.

Your first impulse is going to be to make some deals. You want to get rid of the dudes you were saddled with and lay in some players you actually want. You want to put your stamp on your team. Some of the offers may look downright generous. It’s sooo tempting to pull the trigger.

Don’t. You will end up making deals you regret. Ask me how I know.

You have work to do. Before you make any moves, you must decide on a plan. Should you compete for the title this year or rebuild for the future? To answer this question, you need to know the rules, the players, and the teams in your league. Let’s take each in turn.

Learn the rules

This may seem obvious, but make sure you understand all the league rules. Most keeper leagues have a Constitution or rules document online somewhere. Be sure to read it, and don’t be afraid to ask questions of the Commissioner or experienced fellow managers if you need clarification on something. Most every keeper league has evolved its own quirks and odd rules–make sure you know them before making any moves.

Pay particular attention to the rules involving freezes and keepers–how many players you can (or must) keep, how long you can keep them, at what cost, etc.–as well as understanding the various ways in which you can acquire players (trades, auction/draft, reserves/minors, free agent bids, waivers, and so on). To become a force in a keeper league, you will always be on the lookout for players with long-term upside. Make sure you know the league rules for adding and dropping players from your team.

Learn the players

If you’re an experienced fantasy player, you probably have a pretty good feel for the player pool already. If you don’t, you should rectify that by studying the player universe for your keeper league. Don’t overlook minor leaguers if your league rosters them in any form. Minor leaguers can be just as important as big-league keepers.

As you are studying the player pool, be aware of things like MLB service time and contract status, especially in mono leagues where players could get traded to the other league and disappear from your team for nothing in return. You don’t want to stock your mono-league team with MLB trade bait.

Also, be sure to think about every player as a potential long-term investment. Don’t just think about their value for the upcoming season. What might they do next year and beyond? Are they a win-now type of player, like a solid veteran, or a young player with upside whose talent or opportunity might take some time to develop?

Learn the other teams

The next step is critical in the compete-or-rebuild equation. You need to know how your keeper/freeze list stacks up compared to the competition. Find a set of projections and values that you trust and try to figure out who all the other teams are going to keep. You don’t have to be a mind-reader; this is like tossing a hand grenade. You just need to get close.

You likely don’t know the other managers’ tendencies and proclivities yet, so just make your best guesses about which players are likely to be frozen for this season and which are likely to be in the player pool for the draft/auction. During this process, make a list of players that you’d like to trade for to freeze and a list of players to target in the draft.

For each team, assess their projected freeze list. You can figure how much excess value each team is freezing (in an auction league) or make a cheat sheet showing which draft slots will be filled with frozen players (in a draft league). For instance, if Team A is freezing $125 worth of projected player value, but that value is only costing them $65, then they are freezing $60 of excess value. Figuring out these numbers for each team will not only let you know where you stand once you have assessed your team (next step), but you will have good insight into which of your fellow competitors are likely to be competing for the title, and which are likely to be rebuilding. This will help you know what kinds of trades to offer when you’re ready.

What I do myself is make two passes at predicting freeze lists…I make the first pass based on non-inflated salaries, then I calculate inflation when I’m done, and I make a second pass based on inflated prices. Calculating inflation is critical in an auction keeper league. A quick Google search will reveal many articles about how to do it.

Learn your team

Now the real fun begins. Study your own players in depth and come up with a rough-draft freeze list, accounting for inflation. How much excess value will you be able to freeze? Compare your rough freeze list to the other competitors’ lists. How does your team stack up? Do you have a shot to win this year (or finish in the money, or whatever your goal is)? Or does your team look like an also-ran?

The key difference between a keeper league and a redraft league is that a keeper league requires more strategy and long-term planning. When you’re playing in a keeper league, you don’t run a team. You run a franchise. You’re not just playing for this season; you’re making decisions that could affect your team’s ability to be competitive for years. You have to decide if you want to play to win this season or go into rebuilding mode with an eye to the future.

The compete-or-rebuild decision is absolutely, positively the most important decision you will make for your team. I can’t emphasize this enough. It is critical that you be realistic and make the most intelligent decision you can. If you’re used to redraft leagues, it may feel wrong not to play to win. I totally get that, but the occasional rebuild is healthy and necessary in a keeper league, especially in a competitive league where you must trade several high-quality keepers during the season in order to win. It’s like a planned forest fire–you clear out all the dry kindling with a controlled burn now, so your team doesn’t completely go up in flames later.

Obviously, the decision to compete or rebuild is yours and yours alone, just make sure your expectations are realistic. Most people don’t quit keeper leagues when they’re set to compete the next season. Usually, you will inherit a poor team, and you will need a rebuilding year (or two or maybe even three, depending on the format) to be competitive going forward. If you inherited a stacked team, play to win. But don’t despair if you need to rebuild! Rebuilding can be a lot of fun too. We’ll look more in depth at rebuilding in upcoming columns.

Now you’re ready. You know the league rules, you have a plan, and you know which of your players fit into that plan. You have an idea which teams will be in contention and which may be rebuilding. You know which players you want to target in trade offers, and which players will likely be available in the draft/auction. It’s time to start improving your freeze list with smart trades and other roster moves. We’ll talk more about that next week.

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