By: Chris Dagonas

With summer vacation starting last week, I’ve had an ample amount of free time recently. Much of that time has been devoted to preparing for my upcoming wedding. Smaller chunks have gone to things like grocery shopping, chores, and managing Blackburn Rovers back into the Premier League in FIFA 15.

Why Blackburn Rovers? FIFA allows you to choose to control any team, but I like the challenge of taking an unheralded team, making shrewd investments on limited budgets, and seeing young unknowns become stars. I find that to be infinitely more fun than winning championship after championship with a Manchester City or Chelsea. As an average-sized athlete in sports that tend to favour the tall and strong, like basketball and baseball, the underdog mentality is built into my nature.

Blackburn, you may or may not know, was once a Premier League mainstay, who were relegated to the League Championship in 2012. Since taking over as the manager of Rovers, I have nurtured an underdog mentality in my club, and it has shown as we have defeated far superior teams, like Manchester City and Spurs, in our quest for an F.A. Cup. As you can see, I’m right into this manager thing.

Live look: underdog plans from Blackburn Rovers.

While I have been thoroughly enjoying myself on FIFA 15, I started to feel bored with my fantasy baseball leagues. I mean, how many times can I check potential free agents and offer outrageous trades in a day? Drew Hutchinson for Bryce Harper, maybe he’ll click “Accept” by accident! Despite those ludicrous trade proposals, I consider myself a pretty intelligent fantasy sports player, and decided to try out a website I kept hearing about while listening to various podcasts.

The site is called DraftKings.com, and the premise is simple: use your Paypal account to establish an account, whereby you can enter into various fantasy competitions. For as little as 25 cents, you can enter a contest to win ten, one hundred, one thousand, or even ten thousand dollars. You pick a team of players (two pitchers and nine hitters) while trying to stay under the salary cap. You go to battle against up to 50,000 other players, all jostling for the top 4000 or so spots where you can win some cash, from $10,000, down to $5. Everyone below that is out of luck, and out of their buy-in amount.

I decided to buy into my account with $10, money I had made off various writing projects, and therefore not a noticeable amount–even if I lost it all. On my first night, I entered a $3 contest, with roughly 45 thousand other players, gunning for a top prize of $10,000. I managed to afford Bryce Harper and Mike Trout, as well as Anthony Rizzo and hard-hitting Astros rookie shortstop Carlos Correa. For pitchers, I played match-ups and drafted Ubaldo Jimenez (against the Philadelphia Phillies) and Jeff Locke (against the Chicago White Sox).

I had a good night, and came out as a $7 winner. I more than doubled my entry fee in my first night. I thought it would always be that easy.

The next night, I tried to replicate my process from the night before. Pick good match-ups for the pitchers, draft the best possible hitting talent in the field. How did I do? I came in 14,000th place, and lost my 3 dollar entry.

Well, fair enough, I guess. Can’t win ’em all, right?

I never won again.

DraftKings, and it’s closest rival FanDuel, are the leaders in the daily fantasy sports world. Aside from MLB contests, they also run contests for the PGA, NASCAR, MLS, as well NHL, NBA, and NFL. Having been around since 2009, FanDuel and DraftKings have been growing exponentially in the past few years, as public awareness of their brand and potential winnings has grown.

Sports and gambling go together like steak and red wine. At the root of it, each major league sports owner is really just a mega-scale fantasy sports team manager, gambling on the choices they make to generate championships, or at least high revenues, for their team. While I’m making the choice between Mike Trout and Bryce Harper to win $1,000, at a measly three dollar cost, team owners are investing hundreds of millions of dollars in each and every choice, from their general manager to the price of hot dogs at the concession stands.

The art of the gamble, and the thrill of winning the gamble, is at the heart of North American sports. Of course, professional leagues are quick to denounce gambling on games, especially by its own players, as that opens the door to all manner of suspicious activities. But as outsiders, with no influence on the actual outcome, placing a bet, whether it be on a player or a team, only serves to bring me closer to the sport.

Even when I’m losing, as I did all week. Each night, I looked for an edge; choose the best pitchers, play the best match-ups, stack my lineup, un-stack my line-up, play only hitters who hit in the top three of their batting orders. Everything I did got me the same result–a bottom half finish, no cash, and an increasing frustration with how the entire universe is against me!

On my last night, I was in the money right up until the last game of the night. I stood to win $5, until the Los Angeles Dodgers only managed one run against the Mets. With me holding Dodgers’ catcher Yasmani Grandal and second-baseman Justin Turner, who combined for just eight points, I found myself rapidly dropping from the low thousands, a spot where I could have won between 8 and 10 dollars, to the twelve-thousands, where I stood to win, of course, nothing.

My account finally hit rock bottom on July 3rd, and I have yet to add money to keep playing. Nevertheless, I still find myself occasionally signing in and checking out the contest lobby, hypothetically drafting a team and seeing how they would have done.

Betting on Bryce is usually not a bad thing.

This week Yahoo sports, my long-time fantasy sports home, announced that they will belatedly join the daily fantasy sports community by offering their own version of the popular game. As a default search engine and leader among traditional fantasy sports players, this will only see the popularity of daily fantasy sports continue to grow, especially among novices like myself. While this is good in general, as prize amounts and legitimacy will increase, it also points to a potentially negative outcome.

Namely, like big money online poker, the daily fantasy sharks, about five percent of all players, tend to win about 80 percent of the entire prize pool in big tournaments. In a contest of 40,000 players then, 2,000 players will be taking home most of the money, with the other 38,000 fighting it out for the scraps. Moreover, DraftKings allows multiple entries into one tournament, so one player may actually take up 10 winning spots, whereas little old me with one team, stands at far greater odds to land in the money. That makes me, along with most of my novice brethren, a proper underdog, looking to score a big win against the daily fantasy sports dynasty players. If you don’t have a big bankroll (my ten dollars apparently does not qualify), the chance of winning consistently in daily fantasy sports is near-zero. But it’s not exactly zero, and that is enough to make me itch to join in again.

So, while I might still drop another 10 or 20 dollars or so into my DraftKings account this summer, it will not be with the goal of winning a life-changing sum of money. Daily fantasy sports will never be my day job, as it is for a scant few lucky individuals. But, with the thrill of winning always close by, I may find myself paying closer attention to my favourite sports this year, occasionally holding my breath with a big jackpot potentially in sight.

After all, even the biggest underdogs sometimes snatch victory away from the lions. Now, excuse me while I fire up the XBox, and aim to topple mighty Chelsea, against all the odds, for the FA Cup Championship. No money on the line here, but damn, it feels good to be a winner.