The recent trend in Fantasy Baseball has been the prevalence of daily fantasy sites and the slates surrounding that format. The whole point of the daily game is just that, to be a daily thing. It’s to pick players you like for that day and then when the game, so does your ownership or rostering of those players until you pick who you want for the next day’s games. That isn’t what we’re focused on in this article. The words daily and temporary won’t appear again in this piece from this point on. Keeper and dynasty leagues are the complete antithesis of the aforementioned style of fantasy sports and truth be told, it’s for those players that like to think more than just one year ahead and strategize to build a competitive and winning roster for years to come.
The main principle behind both league formats is simple: players get kept from year-to-year, however that’s where the similarities end for the most part. The drafts allow you to add on to your roster each year with fresh talent and perhaps even reserves in the form of minor leaguers, which we’ll get to later, but for the majority of teams, the core players are already in place heading into draft day. Sure, free agent pickups can help add to the roster too, but that’s a different topic. For the purposes of this piece we will strictly stick to draft plans and strategies.
Knowing your league rules can’t be stressed enough. Seriously know what you’re getting into, especially if it’s a new league for you, or in general. The most common and easily fixable mistakes are drafting based on not understanding how the players should be valued in each league. Keeper and dynasty leagues both involve needing additional years of value from potentially everyone you draft, or buy in the auction draft, so it’s highly important to know exactly how the keeper rules work. Do you have to pay additional money to keep a guy from year-to-year? How many rounds does a player’s value change from season-to-season? How many years do you have a player for? What’s the limit of players you are allowed to keep in any given year?
The answer to most of these questions for a dynasty league is that there are no limits on how many players one can keep and no limits for how long you can keep a guy for. You draft a guy, you keep him ‘til you decide you no longer want him. But that doesn’t mean that you can go drafting guys willy-nilly and hope they work out. That’s a recipe for disaster. It arguably takes more research and planning for dynasty leagues than keeper leagues. Why? The length of time you can keep a player.
Drafting Styles in Keeper vs. Dynasty
Drafting in a dynasty league usually means there is greater value on the young players and potentially prospects if you are allowed to draft minor leaguers. The ability to have a guy on your team from the first or second year of his career into his prime is a great chance to really maximize your roster every year. The trick though is making sure you don’t miss on a guy. Missing on a big name player in a dynasty league is akin to an NFL team missing on a QB in the first round, it can set you back a few years of being able to compete.
Now if you have to give up something to keep players, i.e. draft picks or money in an auction format, that changes the strategy a bit, but it’s still a pertinent strategy to focus on a lot of young players and mixing in the proven vets to bolster the roster. A league like this one, give up a draft pick one round higher than the round the player was selected in to keep him the following year, means that taking fliers at the end of the draft has nothing but upside for you. Someone who takes Ronald Acuna Jr. in the 15th-20th round his first year, could literally keep him for his entire career. That’s just one example, clearly there are a myriad of players that fit that same league format and fliers.
Keeper leagues function a little differently since there is a finite amount of players that can be kept and for specific amounts of years. The year-to-year extra cost makes keeper league owners utilize a different kind of strategy than those that are used in dynasty leagues.
Keeper leagues overall, have a limit on how long you can keep a certain player, immediately separating them from dynasty leagues. In most leagues the limit is in the range of 3-5 years and each year there are increasing costs to keeping said player. Whether that be a higher cost in an auction format or a rise in draft pick in a snake format, it still must be considered when drafting the players in the first place. In a league in which a player can be kept for just three seasons, including the draft year, an owner is trying to maximize those years by focusing on potential prime years or getting into prime years, but that doesn’t mean it’s easy to do. Again focusing on young talent that can be acquired cheaply is almost always key to sustained success in the league, but we’ll touch on that later.
Constructing a Roster
Again we’ll go back to knowing the league rules and how many positions are on an active roster and a bench for that matter. The point I’m trying to make here is that you don’t want to box yourself into a corner with the keepers you select aka keeping too many at one position causing you to be blocked out of that position in case there is a surprise non-keeper. Every year someone lets a player go who they shouldn’t have but if you keep too many guys, just to fill a position, then you have no shot at said surprise player. We are asked on a nearly daily (I know I said it won’t be used again but it’s a different case) basis in the chats, which is a great tool to utilize, about keeper questions, which we love to answer, but so many of you tell us that you are keeping two outfielders already but there’s a third decent guy on the list who you are thinking about, just to fill the position. It’s not just outfield either, third base and corner infield are big for this too. While knowing you don’t have to necessarily worry about a position heading into the draft, can be nice, again with the depth across the board at most positions, why take the chance on missing a guy you didn’t think would be there? The above more references keeper leagues rather than dynasty leagues, but don’t you worry dynasty leagues, we’re getting to you now.
Many who have played fantasy football in dynasty leagues, where they are very popular, know that the most advantageous way to construct a roster is to focus on getting young talent at thin positions. Those of you who took Saquon Barkley in his rookie year are set for the next several seasons with a top running back in a position where there are less and less each year. The same reasoning holds true for baseball. The guy or girl that got their hands on Gary Sánchez a few years ago, will be set at catcher for a long time too and getting a player like that at a shallow position is a big key to winning a league like these year-after-year.
Pitching is a slightly different story in these leagues and one that takes a few different things into account. Obviously no one wants to deal with a player that gets injured, however having a pitcher who undergoes Tommy John surgery, is less of an issue in a format where you can keep them forever, rather than just a few years. How many people in keeper leagues were left out in the cold last year because of Luis Severino not coming back until September because of a spring training injury that was downplayed most of the year? But in a dynasty format, yes it still sucked not to have a pitcher of his caliber on your staff, but ultimately it’s just one year out of many that you have him. Of course there is always the option of dropping the oft-injured pitchers, but in keeper league the price is obviously higher for a guy missing a season than in a dynasty format since you have them for a finite amount of seasons.
Price in a keeper league is much more of an issue than in dynasty since there are generally no prices attached to keeping a guy from year-to-year in that format. Simply keeping an ace for the sake of it never makes a lot of sense, unless the keeper price is an actual bargain. Folks will ask us if keeping a guy like Max Scherzer or Gerrit Cole at 1.5-2 times their projected auction value or for a guaranteed first round pick. Well, why give up more than is necessary is our general argument. Sure having a top-tier ace and a potential top-five pitcher is a great thing to have on a roster but that doesn’t mean you have to hamstring yourself to do it. The best way to construct a roster in these leagues is to look for cheap, young, up-and-coming guys late in the draft, I know…I know I sound like a broken record. But in all honesty, staffing your roster with just a bunch of solid mid-priced pitchers will not get you anywhere in a keeper format. They won’t carry keeper value from year-to-year, since you will have acquired them for basically their cost year-after-year, and odds are they won’t demonstrably help you in any category more than a cheaper guy would.
Saves have become a hot topic of whether or not you should punt or specifically target them in drafts over the last few years. Based on the Drafting Closers piece, none of the top-seven saves leaders in 2019 were the same as the top-seven from 2018 which muddies up this discussion for sure. The best strategy for dealing with relievers in terms of a keeper or dynasty format is to get one guy who has a firm grasp on the gig now and then use late-round fliers or low-dollar bids on guys that have the upside to be a future closer or high-impact reliever and then that gives you a piece or two to carry over. You do not, under any circumstances, want to invest in two high-priced closers in one year. They are just too fickle and it’ll hamstring your roster for the upcoming season and won’t give you any keeper or holdover value going forward, not to mention who’s to say both guys keep gigs throughout the year?
Sustaining Your Success
Everybody wants to win, that’s the whole point of playing fantasy sports isn’t it? But in these leagues, unlike re-drafts, an owner has to have two distinct and somewhat divergent goals: 1) win now and 2) build for the future. Obviously the paramount focus is winning in the year at hand, but we’ve already touched on that in the previous sections, so let's see if we can’t help you figure out better ways to keep your success going. Once again it’s about the cheap and young players, but more so than that, it’s about getting your hands on prospects. Most leagues nowadays have minor league drafts, or sections on the bench to hold prospects for a length of time. Now if you are in a league that only lets you keep prospects for a certain number of years, getting guys that are closer to the bigs is important, but most leagues have an unlimited prospect timeline which opens the door to quite a few more options. The art of finding prospects involves more than just looking at numbers. Sure a guy can put up huge numbers, but if there isn’t a spot for him on the major league roster, he is nothing but trade bait and then are you sure you know where he’ll wind up?
Drafting prospects in typically sparse positions can be a big benefit for you down the road, like Gary Sánchez at catcher or Ronald Acuna in the outfield. If you had either one on your roster for next to nothing, imagine the extra you could devote to other, deeper positions, maybe you could go for that extra big time outfielder, or stack first and third base with top-tier players or get two aces instead of one.
But just getting more extension on your budget or draft picks aren’t the only benefits to prospect-grabbing. They also give you trade pieces to help you win in the current season if you need help in a certain area. There will always be at least one owner who will buy the biggest hype about a guy and give you a very nice piece in return. And yes does that sacrifice goal two for goal one? Sure. But there’s a reason that goal one is the first goal, winning now is always better than banking on potential.
Your prospect strategy in both dynasty and keeper leagues will depend on your league’s rules and format and how other owners tend to build their rosters. So, telling you to focus on nothing but getting all ace-caliber pitching prospects, or all second baseman or outfielders won’t do anyone any good, but realizing who people focus on can help you on goal two. How you might ask? If you know that owner A, B, and C all prefer to use their prospect spots on top-flight hitting spots but owners D, E, F, G, and H all go for pitchers and nothing else, you can see that you have a lot of trading partners by charting a course of mixing targets. But it also allows you to really find the diamonds in the rough in positions the other owners aren’t going after, and ta-da you have a stable of prospects to keep your success going.
All-in-all playing in these types of leagues can really grow your baseball acumen and be a great experience for those who are interested in being more of a GM then a one-year manager, which is fitting given the insights our own Jim Bowden has given on the front office of the teams this year. These leagues also offer challenges not present in re-draft formats, but learning the skills of balancing one-year and multi-year goals will mean nothing but success for you as you dominate your league like a boss!