26 October 2016Last updated

Features | People

You can win ’em all

Want to beat your family and friends at Monopoly and Risk and Hangman? Every time? Try these tips from an expert, says Colin Drury

Colin Drury
30 Sep 2016 | 12:00 am
  • Source:Supplied

They are a traditional and entirely pleasant way to spend an hour or two with friends and family.

The humble board game remains – even in today’s world of online amusements and virtual reality apps – one of the finest forms of keeping kids entertained and bringing adults together; an excuse to both switch the TV off and disengage, temporarily, from real life.

That’s how many people view them. But some of us – admit it – are a little more competitive. We’re a little more like Tom Whipple.

To him, the board game is battle. This gentle pastime is actually a platform for getting one up on your loved ones; a canvas on which to claim bragging rights over nana or your (formerly) favourite uncle. To Tom, the phrase ‘it’s the taking part that counts’ is nonsense.

‘It’s definitely about winning,’ he declares with tongue only half in cheek. ‘At all costs.’

The 34-year-old has just written a book on the subject. It is called, with a delightful lack of restraint, How To Win Games And Beat People; is now available in the UAE; and, within its 200 pages, offers hints and tips on how to take on all-comers at more than 25 family favourites, including Monopoly, Scrabble, Draughts and Trivial Pursuit.

‘Never again,’ says Tom, science editor with The Times newspaper in London by day, ‘do you need to be humiliated at Connect Four by a snivelling nine-year-old nephew.’

Among the book’s highlights are a structural engineer dissecting Jenga, a mime artist talking charades and a one-time Formula One driver offering advice on Scalextric.

Other revelations include the best tactics to gain an upper hand at war game Risk (‘essentially, attack, attack, attack’), and the Monopoly properties that, once owned, virtually guarantee victory. Orange, it turns out.
What drives a person to seek to become perfect at a game? Why spend so much time sharpening your skills at something the rest of us only do when there’s nothing much on TV?

This is one of the first questions I ask of Tom. But, amid the light-hearted advice of must-know Scrabble words and Trivial Pursuit tactics, it’s also a question that quietly permeates his book.

That’s because among SAS soldiers talking about how to win at pillow fights and surgeons offering strategies for Operation (really!), another kind of expert fills its pages. These are the men (and it is always men) who have dedicated years of their lives – often of their spare time – trying to ‘solve’ a particular game.

From the chap who quit his job and spent half a decade perfecting his stone skimming skills (he got a record-breaking 88 bounces before official monitors lost count) to the computer scientist who built a programme that knows the perfect next move for any one of the 500 billion billion possible situations in a game of Draughts, the tome is littered with tales 
of such dedication. Or, if you will, obsession.

Fair to say, the motivation of such men must extend beyond beating Uncle Joe at Christmas. 
‘I think so,’ agrees Tom. ‘Like Nick Berry. This guys has, I’m simplifying here, he’s worked out, for every situation in Hangman, 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 behavioural 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.

Tom’s own quest to become unbeatable began – like with so many world-changing, era-defining ambitions – with a childhood humiliation.

In this case, it was at the hands of his loving Uncle Terry. Said relation annihilated our young hero at a game, long since lost to memory, and then didn’t cease to remind him about it for years. Tom spent a youth swearing vengeance.

Fast forward to Christmas 2013 and Tom’s editor at The Times has just asked him to write a feature about games for the paper. ‘I thought it would be interesting and an awful lot of fun to speak to preposterously overqualified experts and ask their advice on how to win family favourites,’ he recalls. ‘Maybe I still had my uncle in my mind somewhere.’

The resulting article got a thumbs up from the editor and was popular with readers. ‘For me one of the interesting things,’ recalls Tom, ‘was discovering that Monopoly was not just a tedious game of luck but a tedious game of skill.’

And that may have been that. Except as he put the piece together the father-of-two slowly started to wonder if it might extend to a book.

‘I had an agent at the time because I was pitching a far more serious book,’ he explains. ‘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, I had this games idea instead – and suddenly everyone was interested.’

The big question, then – the reason we’re all here – what are the ways to ensure never being beaten at any game ever again?

It depends on what you’re playing, of course. And – unless you happen to be a particularly well-developed computer programme – you simply can’t guarantee victory every time at anything. But by learning a few simple techniques, knowing certain rules, understanding some probability and sharpening specific skills and mind calculations, Tom reckons you can definitely improve your chances of turning the family fun into your own personal victory parade.

The best way to explain this is perhaps by taking each game individually. As such, we’ve done just that. But, first, let’s talk of a game of Rock Paper Scissors that Tom and I engaged in.

The key lesson here is that, if you thought this was an activity based on sheer irrational human unpredictability, it 
turns out you’re wrong. Who says so? Science.

A 2014 Chinese study – a proxy look into complex human behaviour – found that a player’s next choice of shape is often dictated by what occurred in the previous round. ‘Players who just won are statistically more likely to repeat their choice,’ says Tom. ‘But players who lost tend to change in the more “powerful” direction – so, they would move from rock to paper for example.

‘As a participant you can use that information to predict what your opponent will go for and choose the shape that beats it. It doesn’t guarantee you will win but it gives you slightly better statistical odds.’

Indeed, when we play, he wins 4-2. I try and retain some pride by declaring I did well to even get two against an expert.

‘Actually, I get that said a lot,’ comes the reply. ‘It’s embarrassing because whenever I play a game now, people assume I’ll win. And, believe me, I’m still more than capable of losing.’

Victory or defeat, there may be more use to perfecting board game skills than just gaining bragging rights. There’s a suggestion there might be some real-world benefits.

That’s because understanding how simple systems work is often a prelude to getting to grips with more complex problems. If, for instance, you understand orange is the best property run in Monopoly (because its proximity to jail means it is the most commonly landed on strip), then you are actually using a form probability theory that could, potentially, be transferable in professional or personal situations.

‘There’s also that idea that playing games is good for exercising your cognitive functions as you get older,’ adds Tom. ‘But then maybe there doesn’t need to be any external benefit anyway. That’s the glory of games. They have no purpose. They are just enjoyable things to do. Sometimes that’s enough.’

There is one game, I note, as we begin to wrap up, which doesn’t have a chapter in the book: chess.

There are two reasons for this, says Tom. One: because there are already entire books dedicated to the subject (which you certainly could not say of musical statues, which gets a chapter). Two? ‘Chess defies explanation. It’s one of the 
most extraordinary creations of humanity. Computers, no matter how powerful, still don’t know how to play the perfect game of chess – because it is so profoundly complex. So, what could I possibly say with 2,000 words?’

Yet doesn’t that pose a fundamental problem with the book, I wonder? If chess is so magical because it remains unsolvable, doesn’t this book ruin the magic of other games by offering, albeit limited, solutions to them?


‘Maybe,’ he admits with a laugh. ‘But then if you can take away the magic by explaining it a little, maybe the game wasn’t that good in the first place. It’s like explaining the rainbow. By science exploring nature, does it diminish it? I think not. I think the opposite. I think it makes things more remarkable. When you realise the depth and complexity to these very simple games then it makes them more wondrous.’

The top tips

Tom provides advice on how to win at more than 25 games in his book. Here’s some digested tips…

The game: Monopoly

The way to win: Buy orange. Always buy orange.

The reason why: Oranges are the properties that get landed on the most. That’s because they come a double diced throw after jail, which, of course, is the most commonly landed on square of all.

The game: Jenga

The way to win: Use your elbows to steady the structure during your turn.

The reason why: ‘I think most people would be outraged if you use this tactic and would assume it was cheating,’ says Tom. ‘But there’s nothing about not doing it in the rules. I spoke to the inventor and she says she does it, so there’s no reason we all can’t.’

The game: Risk

The way to win: Attack attack attack. Then attack some more.

The reason why: In this war game, strike a fine balance between defending what you occupy and invading more territory. In fact a hard-core, statistical study using a technique known as Markov Chains found attack was always the best option.

The game: Operation

The way to win: Tuck your elbow into your body and hold your wrist with your other hand.

The reason why: These are techniques used by real-life surgeons to maintain a steady hand while performing complex procedures.

The game: Hangman

The way to win: When you’re choosing a word for your opponent to guess, go short.

The reason why: This might seem counter-intuitive – surely a longer word means more guesses? No. Longer words mean more letters. More letters mean more chances of getting a guess right. More guesses right mean more chance of getting the word before your man hangs.

Colin Drury

Colin Drury