Timothy Flindell Caffrey obituary, Oak Park, IL

In memory of

Timothy Flindell Caffrey

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22 Entries

Anita Leto

Yesterday

Oh Tim, what great conversations we had! I loved facilitating with you, having you help my clients, and your reasonable approach to leadership. Thank you for your kindness, service, and always being willing to help. I will miss you.

Tim Montgomery

Yesterday

I have worked with Tim for over a decade with a number of clients and would always look for opportunities to partner with him because of how awesome he was to work with and what a fantastic facilitator Tim was!!! He was such an amazing professional at everything he did, but he always brought more than just his teaching and business skills to our clients because of his ability to connect with you personally. He spoke lovingly of his family. My thoughts and prayers are with you all at this time!!!

Joan M Dasher

August 7, 2025

I met Tim almost 20 years ago when I was a BlessingWhite newbie. He took me under his wing, so to speak, and trained me to facilitate several courses. He was a joy to work with -- so kind, empathetic, caring, funny and encouraging. I learned so much from Tim. Through the years, every conversation we had started with our families -- his love for his family shone through his happy smile as he talked. Tim is the kind of person that comes along rarely; I am so blessed to have known him. Thank you for sharing him with us!

Leah Clark

August 6, 2025

Tim was always a regular on the webinars I delivered. Seeing his name in the chat and reading the ridiculously kind comments he would make always put me at ease. His brand of personal generosity is very rare and I was lucky to know him even the littlest bit. My thoughts are with you, his family, at this sad time.

Deb Berman

August 6, 2025

Tim's humor, joy, kindness, and selflessness surrounded everything he did. As others have said here, a day at work with him was always a Great Day at Work. To Tim's beloved family and friends - I hold you in my heart and wish for you comfort and peace.

Tom Kristoph

August 5, 2025

Working with Tim was never work. He brought out the best in all of us. We all learned something new from him whenever we were together.

Robert Anderson

August 5, 2025

Best work colleague ever! It was so much fun working with Tim. At The Executive Technique in 1986, he kept us laughing even during difficult times. He was warm and enthusiastic - an entertainer - and the ring leader of our work team. My sincerest condolences to his family.

Stace Williams

August 5, 2025

Tim was one of my favorite people at BlessingWhite. We shared so many experiences, work and social. All were memorable, and he made every one better.

One historical gem for me was the "rivalry" with a colleague about who was funnier. In the end, I thought of Tim as The Funny One.

My sincerest condolences to his beloved family and friends. May the memories of good times give you moments of piece, and may you laugh, really laugh, at every opportunity in honor of Tim's example.

Barbara Pelly

August 5, 2025

Tim was an amazing colleague and friend. Working with him and the partnership was special. Always willing to support not just his colleagues but the learners he taught was amazing. He has touched so many lives and he will be missed.

Annie McManus

August 5, 2025

I had the great opportunity to work with Tim. Though our paths didn't cross regularly, it was always a great day when I did have the chance to learn from him. He was a great colleague, facilitator, coach, and always brought humor, warmth, and kindness to every interaction. He will be missed so very much.

Janet FitzGerald

August 5, 2025

I am so sad to hear of Tim´s passing....a HUGE loss to all! He was the funniest character anyone ever got to know, and kept our team at work in stitches with his stories and movies he made with his good friend, Mark for our Christmas parties...so original and creative, and with such a big heart too. My heart goes out to all in his family!

Mary Ann Masarech

August 5, 2025

What a gift it was to work on projects with Tim. The world is a better place because he was born.

Diane DiResta

August 5, 2025

I will always remember Tim for his humor, creativity. and kindness. We had a fun time working at The Executive Technique. He lit up every room he entered. Sending my deepest condolences.

Maxime Patte

August 5, 2025

Il était un homme généreux et intelligent. Il restera pour moi « mister cosmopolitan », qu´est ce que nous avions rigolé avec cela ! Toutes mes pensées vont à toi Katie, à ta maman et à ta soeur. Je garde en mémoire le « au revoir » touchant et émouvant qu´il m´avait fait au départ de l´aéroport de Chicago en 2016 (la photo a été faite à ce moment-là). Bon vent Tim

Tanya Hubanks

August 4, 2025

To Katie: My thoughts are with you and your family. After meeting him at your MBA graduation, it was evident how proud he was of you and your accomplishments. Losing a parent to this heart-wrenching disease is so difficult. You will continue to make him proud as you excel in life. Sending you and your family my sincerest condolences. Warmly, Tanya

Brooke Trumm

August 4, 2025

All my love and deepest condolences to Carrie, Kristin, Katie, and the rest of their family.

Patrick Hoover

August 4, 2025

Tim was unique. He sure was at Aquinas when I knew him. I also thought of Tim as young, very young, forever young. And so I´m both saddened and surprised to learn of his passing. One of a kind, most definitely. As do so very many, I miss him.... Patrick J. Hoover

Jacques Fournier

August 4, 2025

Hi Katie, I never got to meet your dad but, as i was reading his obituary, i could tell what a loving dad he was and how hard it must be for you now. So i am sending you these few words of support from Chicago on behalf of your former colleagues at Lycee Francais. To your mom and to Carrie: my heartfelt condolences.

Jeanne Thomas Bunting

August 4, 2025

No words can express the shock of this news. We shared so many fun memories from high school. Tim was the leader of the pack.
Kristin, I can´t image your grief. You two were made for each other.
Sending love and support to you and your girls during this very difficult time.

Laurie Kattuah-Snyder

August 4, 2025

I´m deeply saddened to hear about Tim´s passing. I´ll always remember how freely he sang and joked, creating an atmosphere where everyone felt welcome to do the same. To Kristin, his daughters, and his siblings-I´m holding you in my thoughts and prayers, wishing you strength, peace, and healing during this incredibly difficult time.

Amy Melvin

August 4, 2025

Sending our sincerest condolences. Tim & family are the best alley neighbors. Leo is forever grateful for the fish tank Tim gifted him a few years ago. Tim´s cheerful greetings will be missed.
Sincerely,
The Malcolm-Melvin family

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