Chris was a cool dude. Cool dad. He would always let myself and my brothers crash time at his pool. He would have music going always and a lot of the time it was Rush that he was trying to persuade me to like. During the summer break he would even take myself and my brothers to McDonald’s for a treat and for them to all play in the play zone. He even let my brother Scott tag along on a Florida trip where my family had never travelled. He was such a nice guy and I will always have a place for him in my memories of childhood.

Thanks Chris

Really sad to hear about Chris. Our families hung out quite a bit when we were young. Driving around on that chopped off car/pickup/peach-mobile. Uncle Joe's miniature train. Playing pool. Building elastic band-shooting 'guns' out of sawed off hockey sticks. Only saw him a handful of times as an adult... most recently at Uncle Joe's and Aunt Rita's funerals. It was nice doing a bit of catching up with him. Although it's sad to think back realizing that was the last time.

Thanks for all the memories. RIP cousin.

CHRIS (Pt 4)

This Chris is also generous. Most of the time. Never complained about flying his kids and their significant others down to Florida every December, but if everyone orders beers AND a steak at Cheryl’s birthday dinner….that isn’t in the budget. In truth he has worked so hard to make sure his family are taken care of later in life (AKA Meg’s Retirement Plan), I took it as my personal challenge to get him to spend it all before the end. Somehow, I failed.

I am going to miss the old guy. I hope to make a few more good memories this summer. I credit him with raising amazing kids, more Nick than Meg, but every family has a black sheep. He is everything you would want in a dad, and is everything men should aspire to be. I think Joe Sr would be proud.

CHRIS (Pt 3)

Cheryl arrives at the table of Uncle’s plus Derek asking “Have you seen Chris?”. No we replied, although Greg mentioned he saw him wheel by not that long ago towards the front yard. I get asked to find him. After the table and I gave Cheryl a speech containing things like “grown ass man” I get up and stagger off to go find Chris. I wander up beside the garage and see him in there asleep, head on the work bench sitting in his chair. Noted. I walk back to the table and sit down.

Cheryl: “Did you find him?”

Derek: “Sure did”

Cheryl: “Well, where is he?”

Derek: “He’s asleep in the garage, on the workbench. He’s fine”

Cheryl: “That is not fine. Why did you leave him there?”

Derek: “Because he’s an adult.”

She huffs and walks off. Not long after I am summoned to the garage. Where I find Chris and Cheryl almost on the ramp into the house. Chris is now 10' from his prior nap location, hitting everything he possibly could while trying to negotiate the normally wide gap to get on the ramp. It was all Cheryl’s fault. At this point Cheryl, myself and Meg are in hysterics.

Chris: backs into the garbage can “Jesus fucking Christ Cheryl, you put all this shit here on purpose”

After playing bumper cars up the ramp and into the house, the next obstacle on the course? Is the stairs.

Cheryl: “Derek, you have to help him, I have had too much to drink.”

Derek: “What? I have had too much to drink!”

Cheryl: “You’re still more steady”

This was almost a mistake. Chris and I are giggling like school girls, purple teeth, purple tongues, I help him up both of us staggering, and plop him into the stairlift. Mission accomplished.

CHRIS (Pt 2)

The first time I made one of these style jokes, I was met with stunned silence at the dinner table. No one expected Megan’s new boyfriend to not only cut his spaghetti with a knife let alone make a joke about Chris’ chair. I just kept cutting my spaghetti wondering what I was doing wrong in this Italian family’s home. Eventually, they got used to it.

It was hard to reconcile this man who loved my crude humour, and devil-may-care attitude about the comedic relevance of his mobility scenario with the guy who showed up at Manulife for a lifetime. Listening to him talk about work, displaying unbelievable discernment in complex situations all while making the insurance industry sound somehow fascinating. Seriously, I credit him almost entirely with making me want to advance my career beyond the shop floor. Naturally, a man with the ability to make insurance interesting had a lot of people stuck in his gravity. He had a shrewd eye for talent, is a tireless mentor and fearless in defence of his people. So fearless, he refused a round of layoffs. That’s right.

Corporate Ghoul: “Chris you need to layoff 15 people”

Chris: “I won’t be doing that.”

Ghoul: “But you must”

Chris: “Nope”

Paraphrasing aside, all the corporate shit I had heard, witnessed and believed all my life, about people who made it to his level of the organization shot to shit in one conversation. You don’t hear too many stories like that in the news.

Beverages. Chris loves beverages. Beer. Red Wine. Girlie Cocktails by the Pool (#SummerChris). This is a good thing as I too, love beverages. Not the girlie ones, obviously. Chris and I loved those things together as the photos of several Pillitteri family events prove with our purple teeth and tongues from arguably the right amount of red wine. Like Nick and Kate’s wedding in the backyard. Just the right amount that at one point we lost Chris in his own house.

CHRIS (Pt 1/2)

Weird title, yet in my life this name is a big deal. At my wedding nearly 10% of all guests were named Chris. Somewhere there is a photo of all of them together. They have shocking amounts of things in common. Most are extremely charismatic, rooms of people are drawn into whatever tale it is they are spinning. All of them hillarious, talented, smart men. Never yet have I lost one, at least for not longer than a few hours. Turns out that day is coming much sooner than I had hoped. Chris Pillitteri is on his way out.

I remember once Meg referred to her dad as tall, an interesting reference considering I already knew he was in a wheel chair, but who was I, a fellow antropomorphically misproportioned person (that is the technical term), to judge. I discovered later that Chris and I are about the same height when seated. She was right about one thing, he was big. Not in the sense I was expecting, nor any other sense I can well put into words, but big. You didn’t fuck with this Chris. You got the feeling that he was the smartest guy in the room, that he probably knew it, and still didn’t feel the need to prove it.

He is the first rich guy I have ever met that hadn’t totally lost touch with the reality of normal people’s existence. “Fixed Income Chris” and “The Austerity” have become running jokes for me that still have tread left on the tires.

Speaking of tires; The chair. Probably my single greatest source of material. I quickly took to signing him up to hair-brained schemes, for jumps, off-road tires and lift kits, winches, and dramatic suicide attempts designed specifically to not implicate Cheryl. Left alone without supervision one time, he rigged up a system of ropes and pulleys in and around the bed such that he could lever himself upright and onto the chair. Looking back everyone else but Chris laughed when I had suggested that very thing at dinner the week before.

HI Cheryl,  I am so sorry to hear about Chris.  My thoughts and sympathies are with you and your family.  Take care.

Stephanie

Dear Cheryl and Pillitteri family, 
We were very sorry to hear about the passing of your dear husband, father, Chris. Our Prayers and thoughts are with you at this difficult time. 
With sincere sympathy, 
Sam & Lina Pillitteri & family

I am deeply saddened to hear about the passing of Chris.  He was a wonderful colleague and will be greatly missed by all who had the privilege of working alongside him.
Please accept my heartfelt condolences during this difficult time.  Chris's contributions and positive spirit left a lasting impact, and he will always be remember fondly.

Kim Scheklesky

I was deeply saddened to hear about the passing of Chris. Please accept my heartfelt condolences during this difficult time .

Chris was not only a wonderful colleague and leader but also a truly remarkable person who touched many lives . I will always remember his positive energy and dedication he brought to every meeting and the kindness he showed to everyone around him .

Deepest condolences to you all. Chris has left a lasting impression on myself and on countless others no doubt.

Thoughts and prayers are with you all.

Cheryl, Nick, and Megan:  Echoing the comments of so many - what a wonderful man to know. Although many of us knew him only within a work capacity, his wonderful personality made working with him a real pleasure and was a window into what an incredible man he no doubt was away from the office. 
May your many treasured memories bring you comfort during this difficult time and always.

My deepest condolences to Cheryl, Nick and Megan. I was so deeply saddened to hear about the passing of Chris. Please know that my thoughts are with all of you during this incredibly difficult time. Chris was a wonderful person, quick witted and had a hearty laugh. He will be missed by everyone that came into contact with him.
May you find comfort in the many memories you created with Chris.

Neel.

My deepest condolences to the Pillitteri family.  

Chris was a kind and patience person to work with and I am grateful to have known him.

Cheryl, Nick and Megan - my sincerest condolences. What a wonderful man Chris was. So brilliantly smart, quick witted, a great smile, great laugh, and so caring and kind. I feel very fortunate to have had the opportunity to work for him, learn from him and  become friends. He will never be forgotten - not by me and not by the countless others that had the pleasure to know him. Sending love and hugs to you all. May God give you comfort in this very difficult time. 

Much love,
Linda Lasso

Dear Cheryl, Megan and Nick,

I am so sorry for your loss.  I worked with Chris for many, many years at Manulife and knew him well.  May your precious memories bring you comfort and strength as you grieve his loss.   God bless you.

Warmly,
Kelli

To Cheryl, Megan, Nick, and Family,

I am deeply saddened about Chris's passing, and I want to express my heartfelt condolences to all of you during this difficult time.

For 18 + years, I had the privilege of supporting and working alongside Chris. He was not only a remarkable leader but also a dear friend whose sense of humor and kindness brightened every day.  Chris always had an open door and a listening ear, and his thoughtful nature made a lasting impact on everyone who knew him.  I have so many funny stories about Chris, like the times I’d find his mouse battery rolling out of his office floor to let me know he needed new one, to his sandwich in the garbage because of our ongoing cheese debate.  ( I always put one more slice then Chris liked, but it was so much fun to always see his reaction when I did ) 

My friendship with Cheryl, Megan, and Nick ( Katie and Ashton) outside of the office brought laughs and cherished memories. 

These memories of Chris’s laughter, leadership, and friendship will stay with me forever. He was a truly special person, and I feel fortunate to have known him.   I am also fortunate to have had some really good quality time with Chris and his family before his passing which was so special for me.

Please know that my thoughts and prayers are with you all during this time. 

With deepest sympathy,
Lori MacDonald

Chris mainly interacted with me at my worst: an “urgent” work matter I needed his help with. 

But he always lead with patience, kindness, and support.  So grateful for having known him. 

To the entire family; my deepest condolences; he will be missed.

Our deepest sympathy to you and your family. Please know that you are in our thoughts in this difficult time.

I am truly sorry for your loss.  I had the pleasure of working with Chris in Group Benefits at Manulife.  His sharp mind and unforgettable sarcastic humour always made working together such a pleasure.  My thoughts are with you and your family during this incredibly difficult time.

Cheryl, Megan, and Nick,
I am so very sorry for  your loss of your husband and Dad.  No one needs to tell you what a great man he was...wise, intelligent, and dedicated to you his family, and his work.  Chris was a good man who will be missed by so many.  Take care of one another and hold your memories close.
Sue Thomas

Chris was my leader through all my years at Manulife.  He was intelligent, persuasive, and he usually won our arguments. He had a wonderful sense of humour and could always make me laugh out loud. He was able to ease my stress and I knew he wanted me to succeed. He was a good leader and a good person. I am so glad I knew him.
My sincere condolences to Chris's family and friends.

My deepest condolences.  I was very fortunate to have  known Chris. He was kind, funny and sweet and will be missed by many. xo

My deepest sympathies to the entire Pillitteri family.  Chris made a big impact on many people and he will be greatly missed.

A great friend - kind, humorous, smart, loyal and supportive. I feel fortunate to have grown up with Chris. It was a blessing to know him and the Pillitteri family. Sending you lots of love old friend. - MM

Cheryl, Nick and family, my deepest condolences on the passing of Chris.
His kindness, sharp sense of humour, humility and humanity will always live on for so many of us at Manulife. I had the privilege of learning from Chris over the years and benefited from his wisdom. I owe him so much from what I know about the business and respected him for leading with empathy and kindness. He will be missed by all.

Doina

Hello,

I would like to offer my deepest sympathy to Chris family .  Thank you.

I am sending my deepest condolences to Trina, Dave and Dave, family and friends on the recent passing of Chris. They say it is what is done with the dash between birth and death. Please be happy knowing that each of you played an important part in Chris's life and gave credence to that dash. Keep Chris in your thoughts and heart to live on forever. Share your memories with each other to help each other through this difficult time. Thought and prayers sent to everyone. ♥

I was deeply saddened to learn of Chris’s passing. He was one of the most inspiring and impactful leaders I had the privilege of working with throughout my career. I feel truly fortunate to have learned so much from him — his wisdom, optimism, and sense of humor left a lasting impression on everyone around him. His presence will be profoundly missed. Please know that my thoughts and heartfelt prayers are with the family during this incredibly difficult time.

Cheryl, Meagan, and Nick,

We were deeply saddened to hear of Chris’s passing. Please accept our heartfelt condolences during this incredibly difficult time. Chris was a remarkable person whose warmth, strength, and kindness touched so many lives, and I know his absence will be felt profoundly.

I hope you find comfort in the love and support of those around you and in the cherished memories you shared with Chris. 

Our thoughts are with you as you navigate the days ahead.

Rahim and Zohra Jadavji

Dear Cheryl and Family - my deepest condolences. I have very fond memories of Chris and I working in GB at MLI with many a Product/Underwriting discussions. May you find comfort in all the memories.

Cheryl , Megan and Nick

Chris was a great peer, leader and friend.  He was an inspirational leader and always willing to share his knowledge. I miss our many discussions about work and family.  I could always count on him to make me laugh or maybe sometimes cry. But he truly cared about what was going on in our lives and our team. 

Thinking of you all during this very difficult time.

Alison and Ken Kells

So sorry to hear of Chris's passing.  My sincere condolences to you, Cheryl, and your family.  I enjoyed working with Chris at Manulife; he'll be missed!

My deepest sympathy to you and your family, Nick.  Please know that you are in our thoughts and prayers in this difficult time.

Megan, I am so sorry to hear about your dad.  My deepest condolences to you and your family.  May your memories hold you up during this difficult time.

Hugs and love, 
Debbie Byers

Cheryl, Nick and Megan, please accept my deepest condolences...Chris was an inspirational leader and a good friend.  I am blessed that I was able to work closely with him for many years... benefitting from his wisdom and enjoying many laughs together.  You are all in my thoughts during this difficult time.

Scott

My deepest sympathies to the Pillitteri family.  Chris was a kind, gentle soul and will be greatly missed by all.

Cheryl and family, my deepest condolences on the passing of Chris. Chris was such an amazing person - kind, full of life, great sense of humour, incredibly knowledgeable, so giving of his time, which I certainly had the privilege of experiencing for 15 years at Manulife. Chris leaves behind an incredible legacy.

Sincerely,
Cori Lawson-Roberts

Please accept my deepest sympathy during this time of grief. Chris will live on in all who knew him.

OBITUARIO

Christopher James Pillitteri

11 diciembre, 1963 – 10 junio, 2025

Westmount Memorial Celebration Centre

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