Underdog Fantasy Baseball: The Dinger

This season marks the fifth year that Underdog Fantasy has run its premier MLB best ball contest, The Dinger. The contest has evolved from a $50,000 total prize pool in 2021 to a million-dollar prize pool this year with $100,000 for first place.

Drafters’ skills and familiarity with the format have also developed and some strategies and core concepts have solidified. The second year, they increased the roster size by one flex hitter and the draft by two rounds. That format has been consistent every year since. I’ve been there playing and covering the contest since the beginning, so in this article, I’ll be a guide to understanding what the field is doing and how we can take advantage of it.

Roster Construction

Let’s begin with the first thing we know. Roster construction has been condensed to a common set of build rules each year. For those new to Underdog, a player can only be a pitcher, infielder or outfielder. This draft season, the field believes it has found the best way to allocate draft capital between the three positions. Thanks to my Stacking Dingers co-host Billy Jones and the data that Underdog provides us every year, we know how often different builds occur.

In 2024, with 30% of all lineups, the 7-7-6 build was the most popular. Based on what I have seen in drafts this year, this will likely be the most common build once again in 2025. When we expand the view to ones that include six or seven players at each position, we’re at 68% of the field. And when we look at lineups that have six to eight at each position, we have almost the entire field. There are still some drafters trying to push the boundaries with five at one position. Why would we do this? Typically, a build with five at one position is because they’re spending a lot of early draft picks at that position and making their bet that those guys will stay healthy and are key performers this fantasy baseball season.

Projections

In the first few years of the contest, some of us owned a competitive edge by guiding our picks through the lens of a good projection system. Not anymore. Projections are table stakes at this point. The best competitors use public projections, convert to underdog scoring and look at them on a cumulative and rate basis. It is hard to find sneaky targets based on the big projection systems out there. Luckily, as FTN subscribers, we can use the lovingly hand-crafted VDP model through their Custom Rankings & Projections tool and Underdog rankings. Vlad takes the time to adjust them for news, but more importantly, he spends time going team-by-team, adjusting playing time that might get lost by the normal algorithms of projection systems. Sorting VDP by the positive delta, we can quickly identify a bunch of players worth over a round in ADP value.

The Outfield Cliff

The outfield cliff comes for us all. When a new drafter comes to Underdog, they are always surprised by how quickly outfielders are drafted. The names of outfielders going in the first few rounds make sense to someone coming over from roto-style fantasy. It isn’t weird to be considering Fernando Tatis Jr. in the first round. A new drafter might be surprised at Kyle Schwarber going at the one/two turn, but a brief investigation of the scoring system brings the home runs and OBP skills into focus as a great player for the format. Things start to get confusing further on in the second and third rounds. Let’s take a look at a recent draft I was in: 

What is happening here? A 12-team draft with Teoscar Hernández and Anthony Santander going in the early third round? Ian Happ in the third round? The previous part of this article suggested that being in tune with projections was important. Still, through that lens, we see many infielders being ignored who project for more total points than these outfielders. The answer is simple: On Underdog, we must post at least three infielder and outfielder scores each week, but fewer outfielders play on a baseball team. That has led to outfielders moving further up the draft board each year.

Let’s look further down in the draft board I shared. By the 11th round, we see the outfield cliff already creeping up. If that isn’t the cliff, then we’re at least Wile E. Coyote running in the air before looking down to realize he will fall. It only gets worse in the final rounds. Even some of the best platoon power hitters have moved to this part of the draft. In previous years, we could get guys like Joc Pederson and Matt Wallner in the 18th round or later. It is still possible that as things play out in spring training, we could get one or two juicy outfielders with larger roles than expected. 

No Belly Itchers

If outfielders have shifted in ADP due to scarcity over the last few years, something must have moved the other way. A plague of injuries and poor performances by early round pitchers the previous few seasons have caused the position to fill the outfielder void. The advance rates on pitchers in the first few rounds have been bleak, too. Drilling down into pitcher scoring relative to position players, we see that, by weekly volume, it is hard for a pitcher to separate from the pack. Even when the playoff weeks come, the top pitchers are the ones that get two starts in one week. An average pitcher with two starts in one week will outperform a one-start week from the top aces.

Looking again at the middle rounds of the previously shared draft in the 11th round through a pitching lens, we see that over half the players taken are pitchers. Expect to see this in every draft this year. The perceived value of pitchers has officially cratered. 

A popular strategy that takes this to the extreme is called a zero-pitcher team. This strategy is defined by waiting to take your first pitcher until this group or later. One to three drafters in each draft will likely be using this strategy. The corollary strategy in fantasy football, the zero running back draft, has also become more popular. Many running back targets that fit that strategy depend on needing late-season contingent value when someone ahead of them on the depth chart is injured or performs poorly. The targets in a zero-pitcher don’t need to fit this same profile. Finding an arm with a lot of inning potential later in the draft becomes easier as their overall ADP falls.

Things may be veering too far in the downward direction for pitchers. Looking at the top lineups in the playoff rounds last year, we see Zack Wheeler as a core player. SAMOLSON won $100,000 on the back of an elite two-start pitcher. The balance of elite points in the playoffs versus the overall inability of a pitcher to separate in the regular season still needs to be found.

A Dime a Dozen

That leaves us with one more position to talk about – infielders. Throughout the draft, an infielder can always be found. There are some obvious standouts in the first round. It is within the range of outcomes that Bobby Witt Jr. or Elly De La Cruz could be the top-scoring player of the year. As we progress in the draft, the likelihood of an infielder outscoring the outfielders at the same draft capital increases. Most drafters spend the latter third of the draft backfilling the infield spots with interchangeably projected players.

That isn’t to say these players are all created equal. They may seem interchangeable on the outside, but they don’t all score points the same way. These players won’t be hitting our lineups every week, so when they do, we want to make sure they do it with the highest impact. There are two types of players to consider – the spike-week generators and the stack partners. Home runs, triples and doubles create a ceiling. Hitters that get these are the spike-week generators that we want. Contact, singles and steals create a floor. Stack partners will be hitting our lineups with their teammates on the weeks the team scores a bunch of runs in Coors or facing the terrible White Sox bullpen. 

Stay Balanced

So what does all of this mean? To me, balance is the key. Build lineups that take all of these things into consideration. If you intend on drafting multiple entries in The Dinger, use some drafts to build the more extreme roster constructions. Pick a few players with more playing time potential than projections assume. Draft an early pitcher or two sometimes and build a zero-pitcher team other times. Don’t take late infielders for their floor contributions.

There lies the ultimate beauty of The Dinger. It was only $10. Take each draft as a new opportunity to try something new, fun or exciting.