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From the profile screen, I could send nmann06.pgo a message, challenge him to another match or add him to my buddies list. Based on his low score in our current competition, I sent him a challenge, which he accepted and I won - easy money. We eventually traded a few messages about Minesweeper and our experience with the site, but he seemed less than eager to take up my further offers to take money from him. Despite the site's community-building features, gambling on WorldWinner felt more like sending e-mails from a video poker machine than meeting a kindred spirit at a blackjack table.
With my internet gambling cherry popped by my first win (I just barely bested the third entrant's score), it was a much less nerve-wracking process to enter a few dozen more Minesweeper competitions. I was scanning the results of these matches when I realized WorldWinner's devotion to skill-based games only went so far. While it's true that there's more skill in Minesweeper than in a slot machine or a casino table games, there is still randomness in the arrangement of the mines. WorldWinner tries to minimize this factor by giving players a free move if they get stuck and are forced to guess, but the fact remains that some setups remain harder than others.
The luck-of-the-draw opponent matching system adds another bit of randomness to the proceedings. Winning a competition depends not only on your score, but the score of the next person of a comparable skill level to enter into a similar tournament. Sometimes a low score will end up winning against some newbie, other times a great score will lose to a shark. It all depends on who happens to enter around the same time as you.
You'd think this would balance itself out in the long run, but the opponent pool is seriously tainted by self selection. This effect became apparent after I got beat in competition after competition by the same two usernames: nnrupp.pgo and estremil.pgo. Occasionally, I'd get an easy win against some fresh meat newbie, but the vast majority of entries and wins seemed to be funneled to these two Minesweeper sharks. It's possible that these guys were just natural Minesweeper experts, but I couldn't help but wonder if I was being set up to take a fall to the house shills, "ringers" meant to prevent WorldWinner from having to pay any real winners.
Tired of losing to the experts, I decided to try losing some money to myself. After you've entered enough cash games, WorldWinner takes away its small nod to human interaction and opens up TopThis!, a competition type that lets you wager money against your median score, meaning you're statistically likely to win half the time and lose the other half. This is where the specter of true gambling addiction can grab you - while man-on-man competitions require you to wait for opponents (and thus take a break when none are available), you can bet money against yourself at any time of the day as quickly as your little mouse will let you.
This is what happened to me, as a mad dash of increasingly frantic TopThis! competitions quickly chipped away at my account balance until it was nothing. I was ready to call it quits and write off the whole experience, until WorldWinner noticed my low balance and tried to win me back with some free playing money. I dived back in, determined not to squander my new bankroll as I had my previous one.