Rex Benson - also known as Kropotkin, 'your tormentor' and a 'headache in 9 letters' - today publishes his 1000th puzzle in the Weekend Herald. Nicholas Jones meets the man behind the clues.

Kiwis brave enough to attempt Rex Benson's cryptic crosswords often end up with conflicting feelings about the man they know as Kropotkin. Some are so strong they need expressing.

Benson, 74, sits in the office below the home in Wellington's Northland he shares with his wife Judith, and double clicks a folder named FANS.

"I love your crosswords as much as I hate them," reads one 2010 email. "I have solved three correctly since I started doing them. I am really proud of that but when I mention it to friends they don't know what I am talking about. You are brilliant."


Sandra writes to say she always looks forward to her Saturday "treat", despite it sometimes taking her days to figure out. "That's the joy of it."

Another fan posts Benson photocopies of his crosswords with the answers filled in, like a teacher's pet displaying homework.

In today's paper is Kropotkin's 1000th crossword (1001 if you count a Christmas bonus edition). To mark the occasion The Tormentor, who is unfailingly polite and wears a woollen vest against the winter chill, has agreed to pull the curtain on the process behind each one.

Benson, a film buff whose living room walls are lined with thousands of DVD cases, pauses when asked if his is an art form.

"I don't know," he says. "It is certainly a skill that I guess I wouldn't say anyone could acquire. Some people think you need a twisted mind."

Benson's lair is a typical home office. On the shelf behind him are filing boxes, a signed 1993 All Black team photo, and stacks of punch cards (Benson's career was in data analysis).

There's also a book, Patterns of Anarchy. Kropotkin is the surname of a famous Russian anarchist socialist philosopher, and Benson still considers himself an individualist anarchist.

At the far end of the office a floor-to-ceiling window frames cabbage trees and the valley below, dropping down to the city's 1980s office blocks and the harbour.

Benson comes here most days for a few hours to work and revise his old catalogue. Two old computers take up most of the desk, one runs the ancient DOS operating system and the other Windows 7 with special crossword-composing software.

The DOS machine's programmed to bring up every word he's ever used (29,200), and the corresponding clue.

The answer comes first, but as Benson enters it the clue is often forming in his mind.

The Guardian setter Duggie Anderson (Crucible) once compared setters to failed writers, shaping and re-shaping very short stories condensed into single sentences.

It's a solitary craft but Benson is grateful for the help of a band of checkers: Alan of Wellington, Phil of Ngunguru, Robyn and Andrew of Waipapa, Simon of Cambridge, Rod of Auckland, and Peter of Auckland.

Setters have a signature - their likes, tastes and habits surface in the crosswords, and getting to know them can help crack the clues.

Rex Benson, aka Kropotkin, in his Wellington office. New Zealand Herald photograph by Mark Mitchell
Rex Benson, aka Kropotkin, in his Wellington office. New Zealand Herald photograph by Mark Mitchell

When Kropotkin's first crossword was published in these pages all those years ago readers were told to be aware of his love of opera, rugby, cricket, wine and pubs "which would never stoop to serving either espresso coffee or focaccia bread".

"He hates special pleading, political correctness and the 'new puritanism'," the introductory article warned. "All this allows him to be a smoker who resolutely enjoys the habit and has never even contemplated giving up."

Benson quit two years later, his last packet of Three Castles tobacco used on probably the world's last smoking flight, from Kuala Lumpur to London.

He's also softened his stance on espresso coffee in pubs, although he sticks to wine.

Benson had his first crosswords published a short time after leaving his hometown of Whanganui to embark on a "very unsuccessful" university career.

He ended up buffing linoleum as a night watchman at the old Dominion Museum and National Art Gallery, hanging around the Victoria University campus during the day and getting the odd film review and cryptic published in the student magazine Salient.

Kropotkin wasn't born yet - he went by the name Sapper Ray The Big-Time Boy.
A Sapper is a Royal Engineer (RE), Ray (X), Big Time (BEN), and Boy (SON).

An old friend still calls him Sapper Ray, but otherwise the name faded into obscurity. Without regular outlets about 20 years went by when he would give out hand-drawn crosswords to a small group of friends.

One was Patricia Herbert, then a political journalist with the Herald and fellow bridge player. Herbert put forward her friend's name when the Saturday paper was relaunched as the Weekend Herald, and Benson made his debut. In an accompanying article was introduced as "your tormentor" on April 18, 1998.

"You will know him as Kropotkin," readers were ominously told. "He uses some of the traditional cryptic conventions but his style is funky rather than classical. And he will challenge your vocabulary with the occasional obscure word. 'Petiole' and 'ischaemia' are two which spring to mind."

Cryptic crosswords usually have two parts - a definition of the answer, and an indication of the answer through wordplay. The straightforward definition is found at the beginning or end of a clue. Most cryptics abide by the formula: definition plus wordplay equals answer, or wordplay plus definition equals answer.

The reward from cracking a clue is proportionate to its difficulty, and Kropotkin's are famously rewarding. They also often deliver a dose of Kiwi humour.

For example: "Stays here otherwise Huka Falls did you say? (5)"

The aim is to work out a synonym for "stays". The "did you say?" part of the clue signifies a homophone at work in the clue - a word or term that sounds like another.

In this case it is "hooker falls" - something which happens in rugby if there isn't support from the props on either side. The answer is "props" (a stay is a supporting rope, or a prop).

It's been almost 20 years of composing Weekend Herald puzzles. The passing of time has thrown up something of a surprise - Benson says he's finding it easier than ever to compose crosswords.

"And I can't really explain that, maybe it's just getting the knack of seeing a word. I just wish I'd started this 10 years earlier. Anyway..."

Still, there's comfort in knowing headaches will be delivered from beyond the grave - he's currently setting crossword 1029.

"It's a funny thought that when I am underground that people will be still enjoying my crosswords, six months afterwards."

75,000 crosswords and counting...

The world's most prolific crossword setter started his craft in the Navy when his air crew banned him from playing cards after seeing him shuffle a pack and deal himself 13 spades.

Now 85 and still setting crosswords, Roger Squires was in 2013 named by the Guinness Book of World Records as the world's most prolific crossword setter.

At that point he had created nearly 75,000 crosswords, published in a variety of outlets and churned out at the rate of at least one a day.

When he was awarded the record, Squires was asked for his favourite clue, and said he had been praised for "Bar of soap (3,6,6)", with the answer, "The Rovers Return".

Solve the puzzle

• Try to identify and solve the easiest clues first - a quick scan of the clues can suggest some which will be the easiest to solve, so start with those.

• Sometimes the shortest and longest answers will be more distinctive and therefore easier to solve than words of middling length.

• Clues that refer to multi-word phrases are often easier as they are more distinctive.

• Don't work methodically through the clues in numerical sequence - as soon as you have entered an answer, try to solve the clues that cross that answer.

Test yourself...

"Slip on icy black slush - that should take your mind off skating! (10)"

"Leila and Clinton ate out in Washington - his own admission (1,6,4,1,3)"
(I cannot tell a lie)

"Robert Scott thus found (6,5)"
(frozen stiff)

"Thatcherite holding a piece of music? (7,4)"
(Maggie's Farm)

"Farmer's gleeful announcement to lambs after tossing? (5,3,4)"
(tails you lose!)