How to Win Every Game Ever Created, According to the Experts

When I first meet Tom Whipple to talk about board games I tell him: it’s not the winning that counts, it’s the taking part. “Rubbish,” he says. “That’s the battle cry of the loser. Board games aren’t about having fun. They’re proxy-conflicts, a way to get one up on someone. If that someone happens to be your nana, so be it.”

He’s joking. But only sort of.

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Tom Whipple is a man who takes this subject seriously. In fact, the 34-year-old, who’s science editor at The Times, has just released a book about it. It’s called How to Win Games and Beat People, and offers the secrets to being victorious at everything from Draughts to Battleships, Charades to Scrabble, Risk to Blackjack, and drinking games to pillow fights.

Among its revelations are the least guessable word at Hangman (jazz) and the Monopoly properties which virtually guarantee victory (orange), while other highlights include a surgeon offering tips for Operation, a Formula One driver dissecting Scalextric, and a former SAS soldier explaining how to demolish all-comers in a pillow fight.

VICE: Most important question: what does an SAS guy say when you phone and ask how to win at a pillow fight?
Tom Whipple: That was Andy McNab. He was so charitable. When I explained what I was doing he just took it totally seriously: “A pillow fight situation? Okay, you’re there to win, so no dancing, no staring—go in fast, hard, and get the job done.” Brilliant.

You also had a world-renowned surgeon talking about Operation.
I did. Roger Kneebone from Imperial College. I’d spoken to him before for The Times so I knew he’d be game. But actually there are some genuine transferable skills between Operation, the game, and operation, the activity that saves lives. Both are about keeping your hand steady. Surgery is more complex obviously, but you can’t remove an appendix if you’re shaking. So these guys have techniques to help them, like tucking their elbow into their body and supporting their wrist with the other hand. It was the same with Johnny Herbert. You wouldn’t necessarily think a Formula One driver would be able to help with Scalextric, but he was adamant there are links. Key for both is anticipation, being smooth on the throttle and accelerating out of corners.

Was there anyone who didn’t see the joke or turned you down?
I tried to get James Blunt for musical statues because he’s was once a Buckingham Palace guard. But he never replied to my tweets. He has, like, 3 million followers, so he probably didn’t see them. And then, just occasionally, I had academics who didn’t see the joke. There’s a chapter on drinking games and I had some trouble with that because those I got in touch with kept saying it was irresponsible to write about the subject. One told me drinking games kill and should be outlawed.

Ah. Still, how do you win a drinking game?
There’s the classic advice: line your stomach. But, interestingly, there’s research which shows the effects of alcohol are more pronounced when drinking somewhere unfamiliar. So if you really want to be last person standing, scope out your venue in advance and go drinking there a few days beforehand.

Good advice. Give me some more surefire tips for other games.
Well, I always thought Monopoly was a tedious game of luck, but it turns out it’s a tedious game of skill. It’s all about buying orange. They’re the properties that get landed on most because they come a double dice throw after jail, which is the most commonly landed on square of all. And I think a lot of people feel that intuitively. But there really is serious academic probability theory that proves it.

Another?
Another might be [Napoleonic war game] Risk. Explaining this is a rabbit hole of math—it’s hardcore, degree-level statistics that uses a technique called Markhov Chains—but, as game players, what we need to know is essentially: attack. This is how you stand the best probability of winning. Don’t consolidate. Don’t defend. Don’t strike a balance. Attack. And in Scrabble, it’s a long shot, but always remember muzjiks, sovkhoz, and kolkhoz. They’re the seven letter words—real words—that score most points.

I also wanted to ask about Rock Paper Scissors, because it’s supposed to be completely random. But you say you can load the odds in your favor.
This was proven by Chinese scientists. They analyzed people playing Rock Paper Scissors, and what they found is that a player’s choice of shape is often dictated by what occurred in the previous round. So players who just won are statistically more likely to repeat their choice. But players who lost tend to change in the more “powerful” direction—they would move from rock to paper, for example. If you remember that information, you can predict what your opponent is likely to go for and then beat them.

Apart from the tips, the other thing that really struck me were the interviews with people who had dedicated so much of their lives to “solving” games. Their dedication is fascinating. Like the Connect Four guy, for example.
Victor Allis. Astonishing. There are 4.5 trillion possible situations that could exist in a Connect Four game, and he created a computer program that would play the perfect move for every one of them. It was literally unbeatable. One claim to fame he has is that Beyoncé—she beat Kanye West 9-1 at Connect Four backstage somewhere, and afterwards she said she’d been reading his thesis. So I could have interviewed Beyoncé—I could have done that, totally—but, of course, I went straight to the man himself.

But what inspires someone—he was also only in his 20s—to work this stuff out? It’s just Connect Four or Hangman, or whatever.
Well, some are academics—Victor Allis investigated Connect 4 as part of his Masters degree, and I guess Connect 4 was a useful way to do research in quite hardcore computer science. And then others might work in game theory—maybe they predict financial markets, for instance—and this is something they do in their spare time. Like the Hangman example. This guy has—I’m simplifying here—worked out, for every situation, the next letter you should choose. And that changes depending on the size of the word you’re guessing, and also what other letters you already know. But he’s a data analyst for Facebook. And that is so complicated—finding behavioral models in an unconstrained system—that it’s probably quite satisfying for him to go home and try to find a solution to a closed, defined problem like this. My guess is, for him, solving Hangman is like doing a Sudoku.

Is that similar to your own motivation for writing the book?
Well, I enjoy playing games and I have a very competitive family, so winning is important. But this started as something I did for the newspaper for a Boxing Day feature. I had an agent at the time because I was pitching a far more serious book. It was a sweeping history of time. I think I had illusions that I was a grand intellectual. But when that failed I said to the agent that I had this games idea instead—and suddenly everyone was interested.

And now it’s finished and out there, are you unbeatable at games?
Actually, it’s embarrassing, because whenever I play a game now people assume I will win. And, believe me, I’m still more than capable of losing.

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