The Telegraph’s cryptic crossword turned 100 this summer. But there’s more to this iconic puzzle than just its longevity. Its history is colourful. And as part of a puzzles portfolio which spans an ever-expanding array of genres across platforms, it’s also the foundation stone of an important part of the brand’s publishing strategy.
“Puzzles are very important to The Telegraph,” according to James Brydon, The Telegraph’s deputy puzzles editor.
“They have historical value. But they are also an important part of what people look for in the paper today — a lot of Telegraph subscribers are very keen to add them onto their subscriptions.”
Word games are as old as language. But the first published newspaper crossword is widely acknowledged to have been devised by a Liverpudlian called Arthur Wynne, who emigrated to the US.
After abandoning onion farming for journalism, Wynne became editor of the New York World, in which his first crossword — he called it a “word cross” — appeared on December 21, 1913. A bit of a slow burn, the puzzle really took off with the publication of a compilation of the crossword puzzles in book form eleven years later.
The Telegraph launched the UK’s first daily crossword on July 30, 1925 — back when the Daily Telegraph, as it then was, cost 2d and had just 18 pages. In those days, there was just one Telegraph crossword, with a grid of fewer black squares today — and fewer cryptic clues.
It became popular quickly, prompting the paper’s decision to launch a Saturday prize crossword in March 1928, launch its quick crossword in 1937, and continue printing its main crossword daily despite paper shortages shrinking the daily newspaper to a mere half dozen or so pages during the Second World War.
Helping the war effort
The Telegraph crossword’s reputation grew during World War II for other reasons, too.
Following a competition inspired by a Telegraph reader’s claim to have completed the crossword in under twelve minutes, some of the fastest crossword players were approached by the War Office, trained for code-breaking work and spent time working at Bletchley Park.
Then there was what’s known as ‘the codenames affair’ — a security scare triggered by what turned out to be a coincidence when in, the weeks leading up to D-Day, several top-secret codenames for the invasion of Normandy appeared as Daily Telegraph solutions.
Over the years since, Telegraph crossword compilers developed quite a knack for compiling themed crosswords to mark major events — the first moon landing, to name just one.
More recently, puzzles have been an important driver of the paper’s digital growth.
“They promote stickiness by generating a strong sense of engagement as puzzlers are very committed, with puzzling part of their daily rituals and routines. They also drive loyalty as puzzlers are highly attracted to the puzzle writers they know and love,” he explains.
And having fallen in love with cryptic crosswords as a child, of all people, Brydon should know.
Starting young
Introduced to crosswords by his parents, he began solving them regularly in his teens — drawn, he says, by the snippets of knowledge he might not otherwise have come across elsewhere. Around the same time, he also began compiling his own on hand-drawn squared paper.
In his early twenties, Brydon submitted some of his crosswords to a student newspaper. He got his first puzzle into 1 Across, a prestigious monthly magazine for cryptic crossword enthusiasts.
While teaching languages (German, French and Mandarin), he worked as a freelance crossword and puzzle compiler for many different newspapers and magazines — including different types of crosswords for The Telegraph — Cryptics, Quicks, American-style Cross Atlantics, and Toughies (known colloquially by Telegraph puzzle fans as “toffees”).
In 2023, he formally joined the paper’s team of back page cryptic crossword compilers. Then, having stepped back from teaching, he joined the paper full-time in a staff role when he was appointed The Telegraph’s deputy puzzles editor in January this year.
“Crossword compilers are a very broad range of people — there is no particular ‘type’,” Brydon says of his trade, which recently inspired the creation of a BBC television detective dramedy series about a reclusive puzzle designer turned detective, Ludwig.
“Some leave school early, some might have been in the forces, some are academics. But what unites them all, like most puzzle setters, is that they are lifelong fans and they have a shared commitment to their craft as it takes a lot of time, thought and effort to hone it and do it well.
“Interest and enthusiasm are, I suppose, the most obvious recurring theme.”
Puzzles editing is a “slightly unusual job”, Brydon readily admits.
“We deal with a lot of people writing puzzles of all kinds for us. They send them in, I solve them, then I edit them. We look for accuracy, tone, the right style. Then we make the changes needed before going back to the writers.
“There’s quite a bit of to and fro.”
Extending the puzzles portfolio
Then there’s new product development.
“Another important part of the job is testing new puzzle ideas,” he continues.
“We’re constantly looking to diversify the portfolio of puzzles we have. We do this using special frameworks we have for testing, doing research, prototyping, amending and working closely with the design team on features that we can add to improve the player experience.”
The aim, Brydon explains, is to keep growing The Telegraph’s puzzles portfolio by adding an ever-widening array of puzzles in all shapes and forms — from word and number games to general knowledge, visual and spatial puzzles, and more.
The best puzzle is “enjoyable and useful” — a constructive and productive way to spend some of your spare time.
“It should engage your brain, make you think, give you a bit of a challenge,” he says, warming to the theme. “But another important part of our approach is to build a broad range because what people want varies by mood, where you are, what time you have.”
Another important consideration is to satisfy the old guard while also reaching the new. This means actively leaning into people’s lifestyle and behaviour and how both shift with time.
In 2022, The Telegraph launched dedicated puzzle website Puzzles — offering new versions of its favourite word and number games including crosswords, sudoku, codewords and kakuro, new word game PlusWord, and new culture crossword, Cross Atlantic.
A year later, it launched a dedicated puzzles app under the same name with enhanced features including Streaks — which allows puzzles players to showcase their prowess, and Achievements — in-game rewards.
In 2024, a trivia game called Sorted launched.
Today, standard Telegraph subscribers can access the paper’s Puzzles package free for the first 12 months then for £49 a year. Non-Telegraph subscribers, however, can also access it for the same price after a nominal £1 charge for the first year.
One important priority throughout puzzle development is to make a compelling user-friendly format. Another is to encourage more people to play more. So, to celebrate the cryptic crossword’s centenary earlier this year, The Telegraph released a new GCHQ-theme cryptic crossword and dug into its extensive archives.
It published 30 of its best crosswords from the previous 100 years — including those from the time of JFK’s assassination, the Wall Street financial crash and England’s World Cup win, ran a series of articles explaining its vintage crosswords’ historical significance, and offered incentives to sign up for a Puzzles subscription.
The puzzler community
“One of the nice things about puzzles is how inter-generational they are,” Brydon adds.
“It’s something people can enjoy doing with their families — kids with parents and grandparents. And we definitely encourage that, as often the puzzle habit is something that’s passed down.”
To this end, The Telegraph recently launched a guesting feature for users to gift five puzzles to someone they know free each month.
Much time is spent coming up with ideas for modern, digital puzzles content for younger people who don’t spend hours with printed paper products and want puzzles that feel contemporary and relevant.
“When we ran vintage puzzles as part of our recent puzzles centenary, we looked at ways to get solvers to comment and share their thoughts and ideas online,” he adds.
As a result of all these efforts, The Telegraph has changed — and continues to evolve — the puzzler experience of solving a puzzle, which was once something quiet and solitary, into something increasingly dynamic and social.
Today, solvers are encouraged to comment and share their achievements with other solvers on the Telegraph’s own site and via dedicated third party puzzles sites, such as Big Dave’s Crosswords blog.
Meanwhile setters — once anonymous, mystery figures — now actively engage with solvers and regularly interact.
That’s the nature of puzzling, says Brydon: solvers are never shy of sharing feedback, or trumpeting their triumphs. Because it’s a personal thing — as it is for the setters, too. And by being so, he believes, it’s all the better for it.
“An important aspect of a Telegraph puzzle is that it’s something that is authored and hand-crafted,” he explains.
“Sometimes we get asked by subscribers, ‘Does AI write your quick crossword?’ The answer is: absolutely not! We stick to the idea that a puzzle is a connection between the person who writes it and the person who solves it.
“A Telegraph puzzle writer thinks deeply about what level of challenge they want to achieve, what things they expect the user to know, how they would like things to be constructed and written — all things that can make the solving experience more enjoyable.”
Today’s digital world has changed much. But while The Telegraph is leaning into that, it is also holding onto something else: the timeless and reassuring appeal of a good puzzle — the challenge of it, then the moment of satisfaction when the answer falls into place.
This article was first published in InPublishing magazine. If you would like to be added to the free mailing list to receive the magazine, please register here.
