February is almost here, and we are getting close to fantasy baseball season being in full swing. Most leagues haven’t even really started going, and many people haven’t thought about how they want to approach the season.
However, keeper leagues are different. Because you will be setting a long-term plan, it will take long-term planning. Every keeper league is a bit different, but some tried-and-true strategies can set you up for success in the short and long term.
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League Format & Rules
The No. 1 rule of any fantasy baseball league is “Know Your Rules.” That is even more important in long-term leagues. Things like position eligibility, keeper length, keeper inflation and penalties will change how you value players and find the weak spots to exploit in your leagues.
You should only use fantasy baseball rankings catered to your league. Do not rely upon standard rankings. Do the legwork to ensure your prep work is catered to your own format and rules.
Competition Window
One of the hardest things for keeper league players to do is commit. At the beginning of a season, you should take a hard, objective look at your team and decide whether you are a team trying to win or build towards the future. Teams that straddle the fence of both usually end up finishing in the middle of the pack year after year.
If you are trying to win now, then you should be focused on the players who help you accomplish that this year. Typically, in these formats, that is veteran players others are trying to get rid of for youth. These older players are traditionally undervalued in the market compared to their actual value because they are baking in the inherent long-term value.
However, if you are trying to win now, you shouldn’t care as much about their long-term value. Remember, “Flags Fly Forever.” Do what it takes to win, even if it means you are sacrificing long-term value.
On the flip side of things, if you know you are not going to be competitive, commit to the rebuild. Trade those players that are getting up in age and stock up on prospects or young talent. If you have an innings minimum you need to hit to not hurt draft picks for the future, load up on bad starters who get innings.
If you have no minimums, load up on the types of players that pay massive dividends in the future. Always shoot for upside unless you are in an extremely deep league. However, make sure you cater your choices to your format. If you can only keep players for a certain number of years, stashing very young prospects may not work well.
Another thing you can do is grab pitchers that had an injury and are expected to be back midseason. These players won’t have a ton of value for competing teams, but a rebuilding one could get a steal for a low price for the 2026 season and beyond.
Understand League Preferences
Often, managers come in with their own ranks and values for their league and do not take into account the preferences of their league mates. Use the history of your league to your advantage. In auction leagues, what is the percentage spent on hitting versus pitching?
Is there a position or category that people tend to overvalue or undervalue? What is often the most available category on the waiver wire? If the price of saves gets driven up at the draft table, you may want to keep a closer at his value price rather than spend more at the draft table. Maybe you know that the league undervalues catchers. Then don’t get the first one off the board and wait for the best deal at the position. Every league is different, so knowing the tendencies of your league will give you an advantage.
This also works for inflation. If you are in an auction league, you need to figure out your inflation rate. Some draft software will do this for you, but if you are not using that type of software, you will need to do it yourself. To do this, first make a spreadsheet that includes the players being kept, keeper prices and actual values. Something like this:
| Player | Keeper Cost | Value |
| John Smith | $1 | $15 |
| Peter Rabbit | $22 | $27 |
| John Doe | $30 | $30 |
| Bruce Wayne | $36 | $44 |
| Peter Parker | $3 | $18 |
| Total | 92 | 134 |
Next, take the total budget in the league and subtract it by the total budget of keepers in your entire league. You then divide the remaining budget in the league by the remaining value to get your inflation rate. Multiply this number (usually between 1.2 and 1.6) by the value you have set out for the player to give you the value with inflation.
Keeper leagues are among the most fun leagues to play in. They allow you to manage in whatever way suits you or you want to try. There is more legwork that goes into them, but that is part of what makes winning a keeper league one of the best feelings in fantasy sports.
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