In Loving Memory of Paul Caldwell

May 27, 1953
Rochdale, England
April 25, 2020
Fairfield, CT
Funeral Home

Spear-Miller Funeral Home

39 South Benson Road,
Fairfield CT US 06824


A celebration of Paul's life will be held at a later date.


Family Gathering


Charity of one's choice in Paul's memory.

Paul Peter Caldwell

Sunday was a gloomy day in Fairfield, CT, appropriate for a world with no Paul Caldwell. His well-spent life ended suddenly on Saturday, April 25th, 2020 taking the color with it. This kind, unassuming and gentle man passed away at home at 66.

Paul was born in Rochdale, England to Leonard and Rosemarie Caldwell. He came to New York City in 1980, taking on its entrepreneurial promise by founding Plaza Design, a marketing and PR firm. It was there that he met his beloved wife, Margaret Hepburn, to whom he was married for 36 years. In 2000, they moved to the town of Fairfield to raise their daughter Emily.

Many hope to make a mark on the world in their lifetime. Paul certainly made his. Good at starting a joke, he could almost never get to a punchline for laughing. Laughing at the laughing became the joke. No one could resist. This quirk was one of the many things that endeared him to so many people from all over the world.

Paul’s generosity did as well. He was efficient in words but generous in time, deed and spirit. He did not have to say much for you to know that he cared. He built life-long friendships, making every friend feel like family. He was always ready to welcome that family to his home with a kiss and a smile. When there was a need, no one was more reliable. He was first to volunteer, lend a hand or just listen.

Paul was a life-long sportsman and an expansive “sports family” grew around him. His first love was rugby, a sport well suited to his tall, broad frame. In his younger days, he was a keen player and active leader first in England, and eventually with the New York Athletic Club “Old Boys”. Later, he took up golf, immersing himself in a crash course in Texas to be able to join friends for rounds at Longshore or Smith.

His most enduring passion was for the racket sport, squash, one he shared with Emily. He was very proud to see her develop into a talented collegiate player and go on to be a respected squash coach. Despite unreliable knees, playing singles and “dangerous doubles” with a regular group of friends was non-negotiable in his weekly schedule. After bashing the ball around the court, he always ended by chatting with whomever happened to be around making sure to ask about their families and what was happening in their life.

As with rugby, Paul did not just play, he dedicated himself to the community as well. He was there in the earliest days of Southport Racquet Club, organizing and participating in tournaments, designing promotional gear and the socializing afterwards. When squash had to leave Southport, he was instrumental in finding its new home at Intensity Squash in Norwalk and formalizing the nascent youth squash programs popping up around Westport and Fairfield.

Most recently Paul led the relatively inexperienced Staples High School Junior Varsity squash team through an impressive season as their coach. It was an appropriate role for a man that informally introduced the game to so many Fairfield county youth players that went on to play college squash. Paul was a gentleman and a gentle soul to his core that felt that sports are essential to the development of a well-rounded person. The example he embodied will live on with the many students he coached and lives he touched.

Paul is survived by his wife, Margaret, daughter, Emily, five siblings in the UK, many nieces and nephews, and his constant furry companion, Bella, the family Border Collie. He will be sadly and fondly missed by all that had the privilege to know him.

A celebration of his life will be scheduled at a later date. In lieu of flowers, the family asks that you donate to a charity that reflects your passion in Paul Caldwell’s honor.

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12 Guestbook Entries for Paul Peter Caldwell

  1. Dear Margaret and Emily,
    We are so sorry for your sudden loss. Paul will be deeply missed in our closed knit squash community.
    Warmest regards
    The Fries family

  2. Taken from us much too early. Paul a man of generous heart and generous spirit, genial and
    popular will be greatly missed all that knew him.

  3. Paul will be missed greatly ! We appreciate the time we had with him on and off the court. The game of long ball will never be the same. Always kind, funny and caring, the squash community has suffered a great loss. Our deepest sympathies to Margaret and Emily !

  4. Maggie and Emily,
    I am so sorry. Paul was a kind, gentle soul, and a true friend.
    I will miss Paul every day, everywhere I expect to see him — at the squash club, on the golf course, puttering about in the garden. He was taken from us too early.

  5. I will so miss seeing Paul at the courts. He was a mainstay of our squash community. So generous with his time to help others learn the game, and a great friend to all. Thinking of you Emily and Margaret!

  6. We are all gutted. It is so tragic and unfair. A wonderfully beautiful human being that will leave such a significant hole in our personal definition of goodness.

  7. Dearest Maggie and Em.
    Words cannot express our sadness at the sudden passing of Paul. We grew up with all of you at Southport. You were part of our squash family, me telling Paul to back off when Em was playing a match and Paul reversing that role when Simon played.
    We miss him dearly but we will never forget him.
    Lots of love,
    Jane and Simon

  8. Dear Margaret and Emily,
    We are sorry for your loss. As part of his squash family, we shared his love of the game and the people we play with. Paul will be missed.
    Our prayers go out to you
    The Van Deventer’s

  9. Margaret and Emily

    Our hearts are with you. It is a most challenging time, particularly without him. Paul will be missed by those of us in the squash community in which he was such a central part. He was a wonderful man and we will always remember him. Let us know if there is anything we can do.

    Bob and Bonnie Kreitler

  10. Dear Margaret and Emily,

    Very sorry for your loss. Paul was a great guy on and off the court and I always enjoyed hitting the ball with him when I had the chance. He will be missed.


  11. Margaret, Emily,

    We are just learning of this now and are so very sorry to hear. Paul was a wonderful part of ours children’s lives and the most dedicated and loving dad. Our thoughts are very much with you.

    Love to you both.

    Aline and William