How I Won $40,000 Playing Daily Fantasy Baseball This Week

A few weeks ago, DraftKings introduced a new contest called King of the Hill. The format is simple: two players qualify for a heads-up match worth $20,000. They play the heads-up match the next day, and whoever wins gets $10,000 and entry into the next King of the Hill (and receives the title of “King”). The King faces whoever won the previous qualifier, and keeps playing these $20,000 heads-up matches until he’s defeated.


Once I read about this new format, I was immediately set on getting into the King of the Hill. As a former high-stakes heads-up poker player, I missed the thrill of playing head-to-head with another player for big money.

Currently, I’m 4-0 in King of the Hill, tied for the longest winning streak in the tournament’s short history. I’ve won $40,000 along the way, and until I am dethroned (so to speak), I’ll pocket $10,000 a night. It has been an amazing ride.

What’s especially great about this format is that DraftKings keeps their qualifiers at a relatively high buy-in ($100-$200), which keeps the fields small and filled with professionals. So far in my four matches, I’ve yet to face a poor player.

For my article today, I decided to look back at my previous four matches and analyze each one. I think you can learn a lot from how each player constructed their lineups, and how a few small decisions can snowball into a win or loss. I’ll make the argument for why I think my lineup was the best approach.

Match 1: Msteinberg09 158.70 – TommyG1979 138.70

TommyG is a very experienced DFS player, so I wasn’t surprised when we both ended up with pretty similar lineups, both of which had fantastic scores that beat the majority of DFS players that night:


One key to my win was our difference at the pitcher position: I ended up using Andrew Cashner as my second pitcher while TommyG went with a seemingly safe bet, the red-hot Felix Hernandez.


I actually used Hernandez as my cash game pitcher on FanDuel — I did not think he was a bad play by any means. I just liked my lineup better with a lower-priced pitcher in Cashner at home against the weak hitting Mets, especially given the Dodgers were playing at Coors and there were a lot of quality plays I needed to pay up for. TommyG solved that problem by using Josh Thole, Ruben Tejada, and Joey Butler, all relatively weak hitters, but very well-priced players in the low $2,000s. Again, I don’t mind that decision at all.

My only issue with TommyG’s lineup was his play of Thole given the weather situation in Washington.

Everyone knew there was a chance the game could get postponed, but TommyG took the risk with Thole. His explanation on Twitter: he liked the value he was getting by paying up for Kris Bryant, and was fine with risking a 0 with Thole. It ended up being a good decision in practice, since Miguel Montero put up a 0 for me and Bryant had a quality game, but I hate this logic, and here’s why.

Bryant is a great young player, but his matchup was not good enough to sacrifice an entire position. No player is good enough, really. We like to fool ourselves into thinking that we know a specific player may crush this lefty, or that Joc Pederson is hitting a HR every time he goes to Coors Field. But in reality, a player can put up bad games, and when we choose a player to use we should consider the chance he has a bad night.


I felt Justin Turner was a way better value than Bryant, and there’s no way TommyG can know Bryant is going to have a great game. That being said, TommyG is a great player and put out a great lineup, and it was a close match. But in the end, I was on top.

Match 2: Msteinberg09 149.65 – Drew “Dinkpiece” Dinkmeyer

My next opponent was also a great DFS player, probably most well-known for winning the Millionaire Maker this past NFL season on DraftKings (and for his vague resemblance to Bill Simmons). Like TommyG, Dinkmeyer is a great player and we both had very similar lineups:


Max Scherzer was an obvious choice here against a high-strikeout Blue Jays team, and with the Dodgers at Coors Field, once again I wasn’t surprised to see both of us using plenty of Dodgers.

The pick that really won me the match was choosing Nick Hundley over Yasmani Grandal.

Grandal is a better hitter than Hundley, but I absolutely loved Hundley’s price at $3,100 over Grandal’s $4,800 pricetag. Hundley may have had a less-than-ideal matchup vs. Zack Greinke, but Greinke is not an elite pitcher by any means, and that $1,700 savings is valuable. It allowed me to spend up for Jimmy Rollins (who was toward the bottom of the order, but still a fantastic play at Coors with a great matchup) while Dinkmeyer was stuck with Ruben Tejada, who put up a nice game but had absolutely no upside.


Don’t get me wrong, I got lucky here that Hundley had such a great game. But in hindsight, I think he was an objectively better play.

I also do like my McHugh play at pitcher slightly more than Syndergaard here. Syndergaard is a great pitcher, but he’s young and I worried about him playing on the road. I also just don’t buy that the Padres lineup is that bad. Syndergaard still had 10 Ks in 4 innings, which is ridiculous, but he allowed a ton of hits and runs and got pulled early. It wasn’t a bad play by Dinkmeyer by any means; I just preferred the safer bet in McHugh for the heads-up format.

Match 3: Msteinberg09 136.10 – Underjones 103.70

Underjones is another DFS pro, and this was one was especially nerve-racking pre-match, as the Rockies game had very bad weather. It was tough to decide whether I should avoid the game entirely. Up until three minutes prior to the start of the 5:05 games, I actually had no Rockies players in my lineup, but switched last second when an L.A. Dodgers beat writer replied to my tweet that he felt like they were going to wait out the weather in Denver.

Use all the resources at your disposal, my friends!


I’m not going to get to very detailed here, but I do want to talk about my pitcher decision. Some people would say that Sale is too big a risk here on the road at Texas for a heads-up, but I think even in heads-up events strikeout projection matters more than anything.


You can’t predict one fly ball turning into a home run, or your pitcher getting enough run support for the win. But you can predict pretty easily how many strikeouts your pitcher will get. The Rangers released the perfect lineup for Sale, batting several lefties including the young, talented but high-strikeout Joey Gallo, and they replaced Robinson Chirinos with a weak-hitting Carlos Corporan at catcher. I felt 7-8 strikeouts was really Sale’s floor. He ended up totally outperforming my expectations here with a 7 IP, 13 SO game and the win, which helped tremendously as three of my hitters (who I don’t regret playing at all, by the way) put up zeroes.

A MLB team’s lineup can have big changes from day-to-day, and sometimes those changes can make what you thought was an unfavorable matchup for a pitcher into an amazing matchup. Make sure to do your own lineup analysis, and don’t just blindly choose a pitcher before you know exactly which hitters he’s going to face.

Match 4: Msteinberg09 138.25 – Youdacao 116.25

I had never heard of Youdacao prior to this match, but he was clearly a savvy player using Jake Arrieta over Gio Gonzalez, even though Arrieta was on the road, his price was higher, and his matchup was not as good. Arrieta is just a better pitcher than Gio, and his low WHIP plays well into the DraftKings format that penalizes for hits and walks.



The key to this match was Youdacao’s decision to not play John Mayberry. At only $2,700 and 6th in the Mets order, Mayberry was my favorite value play on DraftKings going against lefty Robbie Ray at Chase Field. I’m not sure why Youdacao didn’t like him, but it cost him big as Mayberry went for 31 points and single handedly won me this match.

Tonight, I go for my 5th straight King of the Hill win. No matter what happens, I’m very thankful for the luck I’ve enjoyed during this run. Wish me luck and I’ll make sure to tweet out the contest details throughout the night!


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