How My Dad Won $20,000 on Underdog Fantasy

It all started from a $10 entry.

A Lineage of Investing in Players and Obsessing Over Strategies

If you’re not familiar with Best Ball Fantasy Sports it’s a format built for a sports card collector, a stats geek and best of all for someone who is looking for zero upkeep. That’s right, there’s no in-season management, you draft a team and whatever happens happens. No trades, no waivers, no nagging league mates, just pure bliss. The setup might look simple, but it's packed with way more complexity than your typical home fantasy football league. Every Best Ball contest feels like a new strategy game, and figuring out the game theory optimal approach is in my blood.

My grandfather and his three brothers would play all types of board games for hours on the weekend; Monopoly, Acquire, and Parcheesi were their favorites. They would argue as they gambled dollar bills to decide who was the true master of each game. The rules were simply guidelines that could be tweaked however they saw fit. I always assumed that the rule changes were to incite more action among players while also reducing variance; but after diving into two rule changes I think they really enjoyed getting unlucky and then finding a way to still reign champion after a heated 8-hour affair. Two rule ‘adjustments’ that they made in Monopoly were that you needed to pass “Go” one time before you started collecting money, and that you couldn’t make trades or build until every single piece of property was owned. Both of these rules essentially delay action, increase tension and encourage you to look within to see what you could do with the hand that you were given since there were no early negotiations. 

Board games weren’t the only thing my grandfather spent an exorbitant amount of time on - he was also a bobblehead and sports cards collector. With a collection of over 800 bobbleheads and tens of thousands of sports trading cards, he understood the potential in alternative assets. Sure, he liked to collect them and get different variations of players in both collections but he was also forward-thinking, believing that investing in the right player's bobblehead or card could be a way to hold equity in that player, with hopes it could lead to a major financial opportunity.

Unfortunately, he collected most of his baseball cards during the 'Junk Wax Era' of the 80s and 90s, when cards were so overprinted that even the best players' cards have little value due to the lack of scarcity.

Fast forward to 2012, my dad evolved this thought process by casually investing in players through DFS (daily fantasy sports) over at FanDuel. He was an early adopter of the platform and fell in love pretty quickly. FanDuel was also a year removed from Moneyball - the movie that set me on a path to pursue higher education in sport management and data analytics. Needless to say, the timing of FanDuel’s arrival was perfect for the overconfident duo that we were as we tried to win NBA, NFL and MLB contests. 

We played these games for years - it was practically a tradition for me to go to his house on Fridays and build a bunch of lineups together. Unfortunately, part of the tradition was losing by just one player and then spending the car ride home discussing the crucial changes we needed to make to win the top prize.

My dad loved the sweat and so did I, but I hated the feeling of losing in the same fashion each week. I’m sure he did as well, but that didn’t change the car ride back from being a copy and paste discussion of what we could have done differently to win.

Over roughly a decade, he ended up getting a handful of victories on FanDuel but never a 5- or 6-figure win while being a slightly negative ROI casual DFS player.

Converting to Best Ball

Last year was when that all changed. My dad gave up DFS cold turkey. It felt like a slow cash burn and to be fair, DFS is a simulator’s game. People that run simulations, code, and put in hundreds of lineups for each slate naturally have an edge compared to hand building casual players.

That’s when I told him about Best Ball. I had never played before, but I was thrilled to draft football teams in May and the concept fascinated me. The thought process of “if only I took this player instead of that one” would never apply and I love that. 

You draft a team, just like everyone else and then you wait for months to see the results play out. No one has an edge with simulations - Best Ball is a game that is far from being solved.

We would talk about optimizing for the last week of the season, week 17, and about the importance of stacking. I dove right into the deep end maxing out Best Ball Mania and had a top 1% outcome getting 2 of my 150 teams into the Best Ball Mania finals. This feat was through a 2/12 (top 2 out of 12) advance from the regular season to the playoffs, followed by 1/16 advance to the semi-finals, and the last mountain to climb being another 1/16 to get to the finals. 

Essentially, to get one team to the finals there is a .0651% chance - I was like a pig rolling around in mud thrilled to get two teams to the finals. Both of my teams finished just outside the top 100 creating a profitable year and making a memorable year 1.   

My dad didn’t have much regular season success, but finished in 4th for over $1000 in playoff weekly winners - pairing the Lions and 49ers as the foreseeable conference championship game with Mahomes and Kelce. 

He also won an in-season hockey tournament for over $1200 where he stacked his Rangers along with Dallas’s hockey team…don’t ask me the name of Dallas’s hockey team.

After having these wins under his belt and the upcoming baseball season approaching he was talking to me about Best Ball baseball but I was a bit apprehensive. I hadn’t followed baseball religiously for a few years, I used to know not only everyone on every team’s roster, but I would also know their minor league, AAA and AA studs. I took a bit of a break from baseball after an ex-general manager of the Angels screwed over dozens of people in this high stakes fantasy baseball league that I was in (happy to disclose the full story at a later date - not the point of this article).

I decided to look up if there was anyone on YouTube that created content around Best Ball baseball to see if it was worth getting my feet wet and I came across the only channel to specifically discuss this format called Stacking Dingers. I got to hear from three Underdog Fantasy players in Matthew, Brendan and Chris (these guys have bizarre and hilarious usernames in D4RKSH33P,  Toomuchtuma and B3isbol). Their excitement was contagious and I was ready for my baseball viewing experience to be heightened through Best Ball, just as Matthew promised.

I did what I thought was most logical and I used The Bat’s projections - The Bat is the most accurate baseball projections model - to identify which players would be the best for Underdog’s scoring system. This process turned out to be golden as it ultimately landed me on the player that was at the core of my dad’s $20,000 lineup.

The Construction of the $20,000 Lineup 

Using The Bat’s projection, Willy Adames would have the 44th most points of any infielder or outfielder and the 23rd most points just looking at infielders. 

Besides the fact that he projects well, this is someone that has delivered four seasons of impressive production. He had four years of 20+ home runs and two seasons of 80+ RBIs. Both of which were his last two in Milwaukee. 

I’m obsessed with Fangraphs, and diving into the numbers further, it seemed clear that Adames had a new approach at the plate with the Brewers. With the Rays he hit more ground balls than fly balls, but now he was looking to drive every pitch he swung at. 

As you see, with the highlighted ratio of GB/FB, Adames could not stop beating the ball into the ground early in his career, but in 2022 and 2023 he was able to have 44% of his contact as fly balls. In his previous four years at the plate, approximately 33% of his contact was fly balls - these were signs that this player was a screaming buy. Adames had two 20 home run seasons under his belt when the majority of his contact weren’t fly balls - he seemed like an absolute lock to have a similar year to his last two seasons and if that was the case he should have been going approximately five rounds higher in drafts. 

I drafted Adames on 29% of my teams. As you can see (up to this point 9/9/24), he had a career high this past year in fly ball percentage and a career low in ground ball percentage. Simply put, he dominated. This approach led to his first year of 30 homers and 100 RBIs. Unfortunately, if it wasn’t for a Gleyber Torres bullshit 3-run home run in the 8th inning against the Rockies, I would have danced into The Dinger Finals with an Adames team. (I’m a Yankees fan and Gleyber is on my shit list until he’s on a winning fantasy team of mine or contributes to a World Series.) The Dinger was Underdog Fantasy’s largest baseball tournament with a top prize of $100,000.

Luckily, my dad was still alive in their midseason contest - The 7th Inning Stretch.

The night that the 7th Inning Stretch was closing, I asked if he had entered the contest and he hadn’t. I got ten lineups in just because I saw that the contest wasn’t going to fill. I told him it wasn’t going to fill and he drafted five teams.

Only one of those teams advanced to the playoffs. It’s a team that will go down in the record books.

When I got the screenshot of the $20,000 team’s draft board I laughed. Not only did my dad win $20,000 but he drafted against a bunch of huge high rollers on the platform that breathe the Underdog Fantasy app - guys that probably have unhealthy screen times on the app with wives that are waiting for them to put their phone down at the dinner table to notice their children. Here’s the draft board:

From his pitchers, he took a bunch of guys I like - however, my only flag plant was Jack Flaherty. I drafted Flaherty on 50% of my teams. In the Dinger, he was going in the last round, in this contest, his ADP (average draft position) was pick 98.8 which was honestly still probably a round and a half too cheap since he was in the same tier of pitchers (if not more valuable) that went in the 70s (look above if you’re curious who I’m specifically referring to).  

Flaherty was obviously a huge surprise - a comeback player of the year candidate. But for the 7th Inning Stretch it felt silly that there was still trepidation about Flaherty’s season when he had already proved for nearly three months that he was back to being the dominant pitcher he was on the Cardinals. 

His infield production flowed through none other than Mr. Willy Adames.

In the outfield, another flag plant of mine, Joc Pederson - I took 49% of Joc in The Dinger.

For years my dad and I were in a home run pool (you pick players that you think will hit the most home runs). We would take Joc every chance we had as a dart throw to be our fifth guy (top five guys contributed, you would draft eight players). 

Joc dominated in the semi finals pushing this team along to the Finals…but let’s forget about the flag plants for a second.

The construction of my dad’s team is objectively phenomenal. This lineup was crafted through stacks - something that is mainstream/commonly understood to win DFS and Best Ball football tournaments but also very clearly helps win Best Ball baseball tournaments.

It might seem random why certain players are selected, but overcoming personal biases and objectively choosing players who fit into a team-based strategy is key to building a tournament-winning roster.

After our discussions, he knew he wanted Adames - from there, he knew he wanted a couple of guys that typically hit near him in the lineup. That’s where he landed on William Contreras and Jackson Chourio. 

Similarly to football, we draft rookies with the hope that they will be in ‘mid-season form’ or a focal part of their offense at the end of the season when we’re in a position to win these top prizes. This was undoubtedly the case for Chourio. In the Finals, he contributed one more point than Shohei Ohtani and one less point than Willy Adames. This was truly a two-week stretch of being one of the best fantasy contributors in the league. 

My dad knew he wanted Joc (his price never moved…it was pretty insane, a home run hitter at the end of drafts - he was a smash throughout the year) and got the cheapest stack known to man with Joc, Jake McCarthy and Eugenio Suarez.

If you’re familiar with the Badge Bros YouTube Channel and their “Scroll the Fuck Down” mantra you’ll be happy to know that when we were going over the construction of this team, my dad said he was looking for a third Diamondback and that Lourdes Gurriel and Gabriel Moreno were the next in line by ADP. But he kept scrolling and then found Eugenio Suarez who didn’t have an ADP despite having a history of four 30+ home run seasons. One of 49 homers! 

Gurriel honestly would have been a fine click, but Moreno having a higher ADP is a ton of wish casting...home runs are like touchdowns - they’re the biggest contributor to fantasy points. Home run hitters will be relevant even if they have a .200 batting average. Getting a home run hitter that no one drafted in Suarez to stack up with other overlooked players in Joc Pederson and Jake McCarthy was a phenomenal approach.

A Victory Lap Well Deserved

I’m over the days of questioning which player I should have played instead of another - Best Ball is my preferred game. 

It allows the commoner to come in and take their crack at the top prize. No simulation is going to tell you the perfect players to draft because none of them can predict who the top picks will be weeks (or months) down the line when the final round of the playoffs hits. Best Ball is about finding a way to set yourself up for success off of chaos, about creating an opportunity that no one else does. That’s what drafting Eugenio Suarez looks like. 

It made me cringe all summer hearing my dad’s galaxy brain idea of drafting Chase Claypool, the man that was buried on the Bills’ depth chart who received no positive news out of training camp. I tend to think that he over sacrifices prioritizing for week 17 when he reaches in ADP like this:

I also wouldn’t draft this many handcuff running backs, and I wouldn’t be comfortable stopping at six wide receivers with these wide receivers…but what do I know?

The only thing I know is that I would be a liar if I didn’t say that his baseball lineup was perfect.

After over a year of using Underdog, my dad just learned how to name his teams so he can stop clicking on the same team over an over again when searching for a specific team of his. The night of his winnings was when he learned how to click on the individual week of scoring to know exactly how many points each player contributed in that week and he still hasn’t learned dark mode, but he’s done it. He finally had a sweat that will hopefully help him sleep at night.  

As I was told on the night of the win, “Wow, I don’t have to think about the EZpass. (which I laughed at) You laugh, but it’s like $500 a month, I don’t need to worry about it, I now have EZPass money”. 

Yeah you do, and after taxes you have a few thousand left over after that. Let it sink in: you turned $10 into $20,000. A victory lap well deserved.  

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