During Week 16 of the NFL season, DraftKings, a popular daily fantasy sports site, ran a $250,000 guaranteed Main Event that offered up a $100,000 first place prize. All it took was a stellar lineup for PocketFives member Sam Pudge714 Greenwood (pictured) to earn the top spot on the leaderboard after Week 16 had ended. The Canadian was quite shell-shocked at his six-figure score, but sat down with PocketFives to discuss his monumental afternoon.

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PocketFives: Congrats on taking down the DraftKings Main Event and winning $100,000. That’s quite impressive. What was your lineup?

Sam Greenwood: My lineup was:
QB: Tony Romo
RB: Jamaal Charles
RB: Ryan Grant
WR: Dez Bryant
WR: Demaryius Thomas
TE: Jason Witten
Flex: Randal Cobb
K: Shayne Graham
DEF: Bears

I found out about the draft, hopped in the shower, and thought about a general strategy to follow after browsing the salaries. I decided that since the pool was so top-heavy, I wanted to get players whose results were positively correlated, hence Romo, Bryant, and Witten. Cobb and Grant were marginally correlated, but I picked Grant because Adam Schefter announced he was starting at 11:00am and the DraftKings price for him was as if he was going to have his normal, much smaller role in the offense.

Charles, Demaryius, and Cobb just seemed under-priced and Bears D was playing Arizona, which has probably the worst offense in the NFL. Bears D is also a turnover machine and only was like $800 more than an average D.

PocketFives: We would be turned off by having to start a running back from Green Bay. What was your line of thought on Ryan Grant (pictured)?

Sam Greenwood: I didn’t think he’d do well. I just figured I could fill a starting position with a super cheap starting running back and use the money I saved on others. Hopefully, I’d get 10 to 15 points from him and maybe one lucky TD. Two lucky TDs were a very good bink. Especially in these types of tourneys, having super public players can be bad. Even if Adrian Peterson goes off, if 25% of the league has him, you aren’t gaining that much equity.

PocketFives: How many teams were there in the Main Event and what can you share about the sweat?

Sam Greenwood: There were 1,400 teams in the pool. It capped at 1,400 entries and I didn’t realize this until afterward, but I was probably one of the last five entries. I filled out my first ballot, tried to enter a second one, and before I could even load up an empty ballot, they told me the pool was full.

On Saturday, my family drove up from Toronto to our cottage in Quebec, but there was a really bad storm by our cottage and the power lines got knocked down, so we didn’t have any power. And then we shut off the water so the pipes didn’t freeze, so we didn’t have running water either.

On the drive up, I was pretty confident we would get our power back because people around us had power, so I was pretty insistent on driving all the way up to the cottage. My parents thought we didn’t have power and wanted to stay the night in a hotel in Montreal. I finally caved, but was still insistent that I was right, although I wasn’t. We don’t really have internet at the cottage, so if we didn’t stay in Montreal for the night, I probably wouldn’t have entered.

On Sunday, we drove up and still didn’t have power, but when we called Hydro, they give a response like, “It will be ready in 12 hours.” So, we watched the 1:00 games at a bar in town. We drove back up expecting to have power back soon and sweated the 4:00 games on our phones.

We needed Bears D to close the gap. I used up two full batteries on my cell phone by 6:45 and needed to start using my dad’s phone as I manically refreshed the Bears game. Once the Bears scored their second defensive TD, we had the lead, but we needed to fade Cardinals points or hope the Bears forced another turnover or got a sack.

The Cardinals kept driving to midfield and punting and we were worried they would kick a meaningless field goal even though they were down an amount in the game where kicking a field goal would be meaningless for their win expectancy.

PocketFives: What plans do you have for the money?

Sam Greenwood: I split half my action, so I’ll be giving $50,000 of it to my brother. With my share, I have no big ticket purchase lined up yet. Paying rent, investing it, and increasing my discretionary spending isn’t a fun answer.

PocketFives: You have nearly $3 million in tracked scores in your PocketFives profile. Has your poker career been an influence when it comes to fantasy sports?

Sam Greenwood: I think poker does a really good job of training you how to think strategically in all sorts of games. Fantasy doesn’t require the quick decision making that poker does, but 95% of fantasy is not making huge mistakes and not getting too worried when players are on hot or cold streaks.

I think poker players are better at understanding when athletes are running badly. I remember when Calvin Johnson started the season poorly in fantasy and then I heard a stat that he had something like nine catches where he was tackled inside the two yard line.

PocketFives: How did you get started in poker?

Sam Greenwood: I started playing poker on PartyPoker way back when. I also played freerolls on Bugsy’s Club, which doesn’t exist anymore, and then ran my bankroll up very, very slowly. I graduated school last year and in the meantime, I have been helping my dad out with his business. I graduated with a finance degree from McGill. My dad runs a small business, is getting older, and needs help doing deliveries and other manual labor day-to-day stuff, so my brothers and I help him out with that.

PocketFives: We understand that you recently had a competition against fellow PocketFiver Dani ansky451 Stern?

Sam Greenwood: On that same Sunday, I beat Dani in a Toronto poker player fantasy football league. I blew him out and embarrassed him.

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