My deepest condolences to the beautiful Stanford family.  The last time I saw Bobby was at Rod’s funeral and several years earlier he and Rick stopped by Horton’s Gym to say hello.  Bob had a knack for making you feel very special; that great smile and sincere, caring personality was something special.  Bobby played on our first varsity soccer team at SHS, he was a delight to coach.  He will always be remembered by so many he touched; his coach is one of them.

Miss you buddy.  You made the world a better place

My sincere condolences to Bob’s family especially his 4 loving children. 
I’ve know Bob for a short period of time and in that short time, I know that he loves his children so much and he’s a man who is so giving to others. 
He’s the hardest working man I know. 
Two weeks ago, I asked Bob why he didn’t retire. 
I wish I convinced him to retire. 
Bob— you will always be in our heart.

My deepest condolences to Bob’s family. I met Bob through work at USI and over the years feel fortunate to have been able to get to know him as a professional, a father, and a friend. He truly had a heart of gold and a way of making everyone in the room feel “welcomed to the party”. His love and pride for his kids were clearly second to none… when he spoke of them it was always with excitement, care, and adoration.  He will be greatly missed but never forgotten.

This news is devastating to hear.  I met Bob in 1984 when he was living in a Greenwich Yacht Club apartment and working for Reliance Insurance Company (or was it AIG!). I was new to Connecticut and he made an effort to introduce me to his network of friends.  I worked for an insurance broker at that time and he was probably the only insurance rep that I have worked with during my career that I could never stay mad at.  I strangely have a strong memory of Christmas parties with fabulous trees when he was with his first wife.  Heart breaking conversations when he got divorced.  He was a great salesman, and someone that you could trust.  He had such a big heart!  Even with my move across the Atlantic,  he would occasionally reach out via LinkedIn to see what I was up to even though he didn't have any work-related reason to make that effort.  A big part of my heart is broken.   Bob was one of a kind.  Condolences to his family.

A great guy, with a big heart and a good friend.  
Rest in peace Bob, you will be missed. 🙏🙏🙏

You were the salt of the earth here in Greenwich! RIP my friend! 🙏🙏

It seems like yesterday Bob was driving us to hockey practice in my parents stationwagon.  Back when we didnt have a major worry in the world!  Bob was our Captain of the Somerset High hockey team.  It was a team that was like a family and we had each others backs on and off the ice lead by Bob . Never forget the sold out crazy atmosphere of our home games and the lucky to get out alive leaving the away games . We would go back to the Staffords after the game and the parents would talk about the game upstairs and we would have our own festive "gathering"downstairs. I got to play with Bob on the 1st ever Somerset High varsity soccer team which was also full of excitement. Bob will definitely be missed by all and thanks for the memories we will never forget. Even though way to early like Rod.  Rest in peace my friend

So sorry to hear this news. Trish and I send our thoughts and prayers to the entire Stafford family.

To Rick and the Stafford family,

My sincere condolences and Bob will be truly missed! 

Hit em straight up there Bob 🤙

To the Stafford family,

Thank you for sharing Bob with all of us.  I had the pleasure of partnering with him as a client for over 8 years.  He was larger than life, a dynamic leader, colleague and friend. He made an impact on our business and on me personally.  I will miss his easy way, good humor and overall connection. I feel lucky to have known him.

Rob was a great guy every time he came into Garden Catering we would bust chops about his brother Rick he will be missed my Condolences Mike Paoletta Garden catering 🙏❤️

Worked with Bob for over ten years. He was authentic, enthusiastic, optimistic and a prime example of a competitor who refused to acknowledge success was not possible - he always found a way through.  He made up his mind to become the top producer in NY and was a success.  He loved his kids and was so proud of all of them. We often compared notes on many things in life and while we walked different paths, his insights were always endearing and wise with self reflection. He was impossible to stay mad at and was the first to offer help if anyone had a professional or personal challenge. In a world full of those who lack peripheral vision to see others and relate, Bob never met someone he could not find common ground and build a relationship. He will be sorely missed as our industry is a little less kinder and authentic with us passing.

I had the pleasure of working with Bob on some of his clients such as Hertz and I enjoyed his sense of humor. He was a fun person to work with. He was very knowledgeable and cared about his clients. I am sadden by the news of his passing. May he rest in peace. He will be missed by many.

I was caught up short and deeply saddened by the news of Bob's passing.  I remember playing baseball with him across the street from his house on Highview Avenue on this big, undeveloped lot when we were in elementary school, and playing on the Red Sox in the Pierce's Beach Little League with him around the same time.  His dad was coach.  
     Bob was always someone I could reconnect with whenever our circle of friends was either more in-or-out of contact, and then we reconnected again more regularly when we were on the SHS soccer team together in our senior year...Fond memories also of wildly fun visits to U. Maine in the late 70s, when Bob was among our group of unindicted co-conspirators...
     Heartfelt condolences to Bob's family.

Bob instantly became the life of this party!

My condolences to the Stafford Family.  Bob was a wonderful friend I always looked forward to seeing and spending time with.  His kindness, honesty and sincerity was unmatched in my experience.  He also brought tremendous life and energy to every interaction and always kept me on my toes in a fun and loving way.

I, like many will sorely miss his presence and being but we will never forget his legacy as a great human.  
With many fond memories and love,
Mike and Nancy Parent
SHS class of 77

I am devastated by the loss of Bob. We were neighbors for many years at Silo Hill where he was a member of the board. He was always there to help no matter what the problem. I will miss his smiling face. He’s gone way too soon. My condolences to all his family and friends.

To All the Staffords,

Thank you for sharing Bob with us.  We adored him! He has no doubt been a treasured part of our family.  From holidays, hockey games, lacrosse games, family vacations, birthdays, weddings, Innis Arden - Bob was there.  We will dearly miss his big smile and most generous heart.  

Sending our love to you  all-
Tracey, Danny, Connor, Chase, Hannah and Olivia

A great neighbor and a great friend.  He will be missed by all  RIP Bob

Dear Lindsey, Rick and Family,

I am so sorry to learn of Bob's passing.  He was a wonderful man.  You are all in my thoughts and prayers.
 xoxo
Carol Zuckert

Bob was a dear friend who will be sorely missed. Our prayers and sympathies to the entire Stafford family.

The Rogers Family

We are sorry for your loss.  Our thoughts and prayers are with you all in this difficult time
Paul and Pam Downs

Michael and I send our condolences to the Stafford family.Bob was a larger than life presence with his big smile and twinkly eyes.We will miss him.

To Bo, Rick, Lindsay and the entire Stafford family. I heard the sad news last night listening to the Ranger game when Dave Maloney mentioned Bob's passing. My memories of Bob will always be his smiling face lighting up the room, especially when it was the locker room at Innis Arden and he was with his boys. He was always so positive and proud of all of his children, A class act that no doubt will be missed by many.  My sympathies to you all.

45 years of friendship. I miss my very dear friend. Blessed I spent May ‘23’ thru Dec ‘23’ with Bob at his home in Greenwich.  We had a blast. His laughter and smile was contagious. He lit up the room wherever he was, always upbeat. Bob truly lived life to the fullest. Without him mine will never be the same. God bless you Bob 😢 till we meet again in Gods kingdom……BobbyT

Bo, Spencer, Bob and Larry in Rhode Island for the Oce States Bantam year. Those were fun Days

To The Stafford Family 
Our Condolences to you all.  Bob will be missed by all, I  truly will miss our times together we spent at  the rink , driving all over the east coast, vacations the family spent together like Nantucket Golfing, meals out  and most important the friendship and love gave to us.  It was too long since we last saw each other, but your memories and love of life you created will last forever, and is fresh in the minds of all. You touched my whole family, and that will remain in us forever.   I  will never forget all you did for me and more important all of us around you ,  and how caring you   were with the kids.   We will Miss you Bob.

Larry, Spencer, Scott and the rest of the Sodokoff,s

So very sorry to hear of this great loss. Bob was a giant in many ways, a warm wonderful person, a friend who would take his shirt off his back for you, and a great family man and athlete.  He will be missed greatly.

Rick, Lindsey and family,
What a great loss. It was such a great pleasure to get to know Robert, truly the best guy ever. Robert had a bigger than life personality, such a big heart,  fun, kind, generous and a true loyal friend. I will miss him dearly.  The memories of him will always shine bright.  I’m truly sorry for your family’s loss. God bless your family
Xx Christine

We sadly lost a beloved member of the Greenwich community. Bob’s gregarious nature and his love of family were admired by all those that knew him. Bob was taken too soon but will always be remembered as a loving father and devoted friend.

To the Stafford family , so sorry for your loss , my condolences to the whole family, Bob was a great friend since childhood may he rest in peace 🙏🙏

Rick, Lindsey and family,
Mike and I are so very sorry for your loss!  
You’re in our thoughts and prayers!
Sue and Mike Golden

Bob was always such a welcoming person whenever I saw him.  He was friendly, loving and giving.  He had a great attitude. He was an amazing father as well as a fantastic brother and son. The love between Bob & Rick was so clear, it is a beautiful thing to see. Bob will be deeply missed by so many people. Everyone knows Bob Stafford. He is the type of person that brings a smile to my face. The entire family is in my thoughts and prayers.  My deepest sympathies, Luisa Cobb

I am shocked and saddened to learn of Bobby's passing. The Stafford's house was like a second home growing up in Somerset. 
So many great memories, I am laughing and crying at the same time.
Bobby turned into the spitting image of his Dad. They could have been twins 25 or so years apart.
My sincere condolences to the entire Stafford family. Bobby, like Rod, was taken from us much too soon.
My thoughts and prayers are particularly with Mrs. Stafford.  My her family be her strength.

Bob and I grew up together. Elementary, middle school and high school. We just spoke last week about him moving to Florida. I’m devastated. My love to his mom his kids his family I will never forget him.

On behalf of the entire Class of 1977 of Somerset High School, please accept our deepest sympathies on Bobby's passing. We will keep his children and family in our thoughts and prayers. We will miss him.

My deepest sympathy to Bob’s children and family. I worked with Bob at AIG and he always told me how wonderful his children were. He loved you very much. I am so saddened by this terrible news. God Bless him.

So so sorry Rick and Lindsay to hear this very sad news ! Remember Bob from the the wedding , he was such a nice man ! Thinking of you all and sending our condolences .
David & Carol Ann Kneeshaw

Thoughts and prayers to Bobs family and friends.  I had the opportunity to meet and pleasure to work with Bob during my days at USI.  Hearing the news of his passing is heartbreaking.   Bob was great guy who will be sorely missed.  
Rest in Peace Bob
Mary Cooke

OBITUARY

Robert Henry Stafford III

May 23, 1959 – February 18, 2024

Leo P. Gallagher & Son Funeral Home

Show your support

Add a Memory

Share Obituary

Get Reminders

Past Services

Visitation

Funeral Service