Dynasty leagues require their own set of strategy and player valuation, whether you are starting a league from scratch or preparing for your league's 25th anniversary draft. Before delving into some of the intricacies of dynasty formats, an important distinction must be clarified: the term keeper and dynasty are often used interchangeably. While there's no textbook definition, dynasty leagues involve little player turnover, whereas there is considerable churn in keeper formats.
Generally, dynasty leagues retain most, if not all their roster from season to season. Keeper leagues feature contracts with an accelerating cost and term limit. A significant number of veteran players are either cost-prohibitive or on expiring contracts, thus available to be drafted. Depending on the league rules, rebuilding in a keeper league can take as little as one season. Meanwhile, those looking to compete for several straight years in a true dynasty league must commit to a multi-season effort of focusing on accumulating long-term talent and less with winning now.
With that as a backdrop, here are some considerations when joining and competing in a dynasty league.
Long-term Viability of the League
This isn't only about the possibility of investing several years of an entry fee only to have the league fold when you're ready to compete. Time is valuable and you don't want to spend endless hours in a league played even for just bragging rights if you won't be able to pound your chest when the plan comes together. Obviously, starting a league with friends is optimal. Joining a long-established league helps alleviate some of the concern, but also eliminates the fun of building from scratch. This isn't meant to be a deterrent; just something to keep in mind if playing the long game.
Understanding the Intention of a Prospect List or Ranking
When researching for dynasty play, you'll no doubt study assorted prospect lists or rankings. Be cognizant of the intended audience. Some are non-fantasy, thus factor in defense and position while downplaying stolen base potential in this power-laden environment. A slick-fielding shortstop will rank higher than a fire-balling reliever with a chance to close right away. Lists designed for fantasy will better account for speed and saves. Even when looking at a fantasy baseball prospect list, make sure you know the agenda. Some, like ESPN's Top 50 prospects for 2020, are fashioned for immediate help thus favor lesser prospects with a better chance to debut sooner. Others are specialized for long term, like dynasty leagues, and may mix in active players and prospects, like Tristan H. Cockcroft's Dynasty rankings, where you might find 17-year-old Yankees prospect Jasson Dominguez mixed in with veterans like Edwin Encarnacion.
Regardless of the source, always search for lists or rankings with an accompanying player blurb. Information such as injury history, ability to stay at their position, flaws and ceiling are integral when balancing risk on your squad. You'll need some upside plays, but too many can leave your roster short on depth. On the other hand, overloading safe plays avails depth, but can yield a roster devoid of the high-end juice needed to dominate.
Initial Strategy: Win now or build a foundation?
Hopefully, you're able to make this decision independent of the league viability concern. If not, perhaps you're in the wrong league. The chief deliberation is drafting to win or dedicating multiple years setting a foundation to compete for several campaigns. The sticking point is that it's extremely difficult to accomplish both. When attempted, neither are usually executed to maximum efficiency. There's always a few in the league going all-in to win right now, or full-blown prospecting for three years down the road, so you're behind both if you don't pick a lane. It's your team, hence your call, but the best approach is picking a side and funnel the bulk of your draft capital in that direction.
If you opt to compete for the championship off the bat, keep in mind the older, boring but productive players will slide even further than in standard drafts. Similarly, injury-prone players will fall. While you never want to plan a strategy entailing building around a player you're targeting in the 15th round, take stock of the older players you like and get a feel for those most likely to drop.
When going for it in the first year or a dynasty league, a great approach is drafting older but still top-notch pitching. This season, Max Scherzer, Justin Verlander and Zack Greinke are some prime targets. Younger arms like Jack Flaherty, Walker Buehler and Shane Bieber may even be drafted before the veterans. Read the room. If you can grab an established bat first, then follow with an established ace, you're well on your way to capturing the inaugural flag.
If the plan is laying the groundwork for an extended competitive window, acquire proven major league talent before plunging into the prospect waters. As will be discussed, a typical multi-championship base takes three to five years to build, so focus on players still in their prime for eight or nine seasons so they're at the top of their game when you're ready to win. As such, earmark hitters no more than 24 years old. In today's climate, prospects are promoted sooner than ever so there's a decent inventory from which to choose. Mike Trout is currently 28 years old. Chances are, he's still going to be a solid player when he's 34 or 35. However, Ronald Acuna Jr. and Juan Soto will still be in their late 20s and likely more productive. Similarly, Rafael Devers and Vlad Guerrero Jr. are better options than Nolan Arenado and Anthony Rendon while Bo Bichette and Fernando Tatis Jr. are superior picks than Francisco Lindor and Trevor Story.
Laying an infrastructure of current major leaguers likely precludes acquiring the very best minor league prospects. Don't fret. In a first-year league, everyone is available. After Year 1, the fantasy draft is mostly emerging prospects and those selected in the June Amateur Draft or signed at the early July International signing bonanza. By virtue of your team not faring well initially, you'll probably have first crack at the top prospects for a couple of seasons. Your competitors eschewing major league talent for prospects must hit on all of their picks to keep up with you, and the chance of that is slim.
Don't Ignore Pitching
A fundamental tenet of keeper formats is constructing a freeze list composed mainly of hitters as they're more reliable. Then, in-season, deal to fortify pitching by sacrificing some of your keeper assets if in a position to compete. Trades of this nature occur in dynasty leagues, but as will be discussed, are far less frequent. Since dynasty leagues entail retaining most of the roster, competitive pitching needs to be a part of your year-to-year consistency as it can't be as readily acquired. Perhaps when deciding between two top prospects, tie goes to the batter, but at some point, chances on a stud starter must be ventured.
It's still recommended not to chase top relievers, especially in today's landscape. Depending on league depth, closers emerge from the non-drafted pool. In addition, closers have a much shorter shelf life than starters and position players. Ergo, they're more freely available in trades as fantasy managers won't be sacrificing their future by dealing a closer.
What to Look for in a Prospect
Most importantly, you're not going to get everyone right. Don't sweat it, no one will. However, there are some traits to prioritize when prospecting.
Age-to-level is key. A good rule of thumb is prospects should graduate Double-A by 22 years old and Triple-A by 23 years old. Though nowadays, the top prospects are accelerated. How a young player performs the second time at a level is integral. It's prudent to allow an adjustment period, so if a player struggles in Double-A after being promoted during the season, put more heed into how he plays to begin the following season, assuming he's still at Double-A.
Even though there's less shame in striking out in today's game, plate skills are still a great litmus test. It's not perfect; Jeremy Heredia was once ticketed for fantasy greatness based on advanced on-base skills, but they failed to manifest at the major league level. Earlier, it was suggested to find prospect information with player profiles. Look for batters noted to have advanced plate skills or those projected to develop them. Often, scouts can pick up tells not captured via number-scouting alone.
Don't overthink doubling up at a position, especially shortstop. If two youngsters develop into major league studs at the same position, you'll be able to move one for help elsewhere. Plus, prospects are frequently moved to new spots, especially shortstops. The stud shortstop prospect you passed on due to your depth at the position could end up being a star third baseman or even an outfielder.
Drafting catchers is tricky in dynasty formats. A lot depends on whether it's a one- or two-catcher league, and the number of teams in it. Still, regardless of the format, rostering a top catcher is a great way to get ahead of your competitors since many treat it as a luxury, and not priority. That said, catchers often take longer to develop and flame out at a higher rate. If you have a shot at what's expected to be a generational talent like Adley Rutschman, take it. However, keep in mind there was a time Matt Wieters was purportedly Mark Teixeira with a catcher's mitt. Still, the potential edge Rutschman offers in six or seven years is worth the shot. In lieu of drafting an elite backstop prospect, the spaghetti method (throw a bunch against the wall to see what sticks) is next-best. Even in a first-year draft, there will come a time the most promising prospects are exhausted, leaving mostly speculative plays. Contemplate selecting several of the top remaining catching prospects, especially the young ones with advanced defensive chops but raw plate skills. Often, the characteristics fueling strong glovework, like hand-eye coordination and quickness, translate to the batter's box. It's worth sacrificing a few back-end roster spots to land a future star receiver.
Trading to Win
If you win a traditional keeper league without dealing away a significant portion of future potential, shame on your league mates. As mentioned, retooling in keeper formats isn't nearly as time-intensive as dynasty leagues so a repetitive win-rebuild-win-rebuild cycle is viable. In dynasty leagues, one of the most critical factors towards winning is knowing when to pull the trigger on a deal putting you over the top without shortening your window to compete. Elite prospects are dealt all the time in keeper leagues, but they're rarely moved in dynasty formats. Flags fly forever. Winning a fantasy league of any format is hard. Ultimately, it's a balance between how much you want to win right now and how much of the effort you put into getting into this position you're willing to now sacrifice, lessening the chances to repeat. There's no magic formula; it's your decision.
How Long Before I Can Compete?
Perhaps the Holy Grail of dynasty league pontifications, there's no one-size fits all answer. Choosing to begin a new dynasty league with the intent of building a foundation takes less time than dismantling a contending team at the end of its window and restocking. League size and roster depth are factors, but the former could take as little as two seasons while the latter might involve four, if not more years of practicing excruciating patience. At minimum, figure one year of competing for every two seasons of building. The longer the setting of the foundation, the better the chance of extending the window or opportunity.
There are some means of accelerating the rebuilding process. Given, trading of top prospects is scarce, targeting high-risk youngsters could net a future superstar... or a dud. Focusing on those with an injury history they might overcome, or great athletes with unpolished baseball skills can sometimes prove fruitful.
Here's how to possibly get a stud; your string of competitive seasons will no doubt cease. Making the tough decision to bail on a still-good-but-not-great team can often accelerate the rebuild since you have commodities the top teams may want to win. Decide how long you want to spend refreshing and deal away anyone who won't be productive come your next window. As an example, say this July, you decide it's time to play for the future and are willing to rebuild for three or four summers. Gerrit Cole is the cornerstone of your staff. Despite signing a long-term major-league deal, he's going to be between 33 and 37 years of age when you're ready to make another extended run. Cole is a current difference-maker. You may not get Wander Franco or Jo Adell for him, but the uncertainty in pitching prospects could mean Casey Mize, MacKenzie Gore or Jesus Luzardo are possible. Someone with major league experience like Chris Paddack is in play. Jacob deGrom is another candidate to move in order to score a potential young stud. A younger, seemingly healthy hurler like Cole or deGrom will command more than an older guy like Clayton Kershaw or Max Scherzer or a health risk such as Chris Sale or Noah Syndergaard. Those four will likely only net you the high-risk prospect alluded to earlier.
Wrap-up
Ultimately, a 10-step process to dominate dynasty leagues doesn't exist. However, there are several pathways to increase odds for success. The allure of dynasty leagues is, even if you never win, the experience learning about deep minor leaguers is intensely satisfying, embellishing your enjoyment of the game. It's such a kick to latch onto a kid in Rookie Ball and follow his progression through the minors. Not to mention, playing in dynasty leagues often leads to attending local minor league games to see your prospects as they come through town. Admittedly, dynasty leagues aren't for everybody, but for some, they're challenging, rewarding and a blast to play.