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42 Entries
Tommy Aplington
March 8, 2022
I will miss you dearly my friend. A big smile, a great story and a great time were always to be had in your presence. Rest easy, Jimbo. The whole of the North side will always miss you.
Nancy Quinlan
March 7, 2022
Jimmy,
You were one of a kind! If a room full of people were laughing, you were likely holding court. So very saddened to hear of your passing and will always remember you fondly. Til later, Jimbo!
Prayers to the entire Dooley Family and all who loved
Tony Lala
March 7, 2022
Prayers for the Dooley family. We are sorry to hear about Jim. May God bless the family.
Mimi Newton
March 6, 2022
Dear Mary Ann and Family:
I want to express my deepest sympathy for the loss of Jimmy. Everybody loved Jimmy! My thoughts and prayers are with you and the Family during these difficult times.
Mick scanlan . Dublin
March 6, 2022
Sorry to hear of the passing of Jimmy. One of Chicago and life's characters . My symphaties to all his Family and Friends
Maryl Gordon Kavanagh
March 6, 2022
"Your loss is Heaven´s gain."
Although my path never really crossed with Jim, I know he was loved by so many. My heart breaks for your loss, but he is in good company now....back with his dad in God´s loving hands.
Diane Quinlan Fleming
March 5, 2022
To Rob, Dawn and the entire Dooley family
Sending my deepest sympathies and prayers to all of you on this tough loss. May Jim Rest In Peace.
Arlette McKenzie
March 5, 2022
Rest Easy. Prayers for your family for comfort and strength.
MKP
March 4, 2022
This one hurts. It´s unbearable. Jim was a real friend and our relationship was filled with gossip, secrets, goals, diets, late night phone calls, repeat stories, a mutual devotion to pizza, support, tough love and of course laughing uncontrollably! I plan to re-read every text and die laughing for years to come. I can´t help but feel mad at you for this massive hole in my heart and will miss our arguments. RP & Lous will never be the same! Love you forever...
Bobby Diamond
March 4, 2022
A personality that embodied humor, insights, defending those who were being picked on. An integral part of the fabric of Our entire North Side...loved you Jimmy. Prayers for the entire Dooley Clan & those who he touched: from the junior guards he shepherded to the peers that always looked forward to seeing him.
Tim Feldheim
March 4, 2022
I am so very sorry to hear of Jimbo's passing. A unique individual who touched many lives and was one of those guys who made Rogers Park so special. The Feldheims are thinking and praying for all the Dooley Family!
Grif Healy
March 4, 2022
RIP
Timothy Doubek
March 4, 2022
My heart is saddened, Jim Dooley, a special human being to all he knew, hilarious and unique, found a way to relate to everyone he met. A connoisseur of classic Chicago food, curious about the differences of the north and south side of Chicago which we often discussed, will miss seeing him at Bernie's after a ballgame at the Friendly Confines. My heartfelt sympathy to the Dooley Family and to all those close to Jim.
Claudia Kelly Goodwin
March 3, 2022
Pretty sure Jim has already put together a Softball team in heaven. No one seemed more excited to hit that ball in the summer at Rogers Park than Jim.
Thanks for the many laughs Jimbo.
And heartfelt condolences to all the Dooley´s.
Kevin and Melissa Pittner
March 3, 2022
Utterly shocked to learn of Jimmy´s passing. The Dooley clan and the Pittner brood seemed to keep tabs on each other vicariously through our parents. Our hearts, thoughts and prayers go out to the Dooley family and all of their extensions. Until we meet again, may Gid hold you in the palm of his hand.
Jonathan Dela Cruz
March 3, 2022
Rest easy, Jimbo. You´re one-of-a-kind. Condolences to all the lives you´ve touched.
Matt Fearon
March 2, 2022
Rest In Peace Jim
Carolyn Schulz-Moritz
March 2, 2022
So sorry to hear this news. Sending his family and friends prayers. I can just see him skipping his way up to those pearly gates... Rest in peace Jim.
Kellee Keehan
March 2, 2022
Our condolences to the Dooley family. We were devastated to hear the news of Jim's passing.
One thing I would like to say about Jim is whenever he walked in a room everyone had the same reaction, JIM!! I think that says it all. About his life, who he was, what everyone felt about him. It's an accolade that to me is more impressive than any milestones one may acheive. He was unique, intelligent, funny as Hell and one of my husband's best friends. I often asked Mick why he was laughing so hard and it was usually a text from Jim that had him in tears.
He loved to annoy the Laarveld sisters but somehow I was never angry with him. He had a way of annoying me with charm. We knew he loved us ... and we loved him.
He will always be in our thoughts, stories and memories. Jim please give our love to my brother and all we've lost from the RP when you arrive in Heaven. I know they'll all yell JIM !!! when you arrive. Godspeed.
Suerth Craig
March 2, 2022
Godspeed Jimbo. Deepest sympathies to the Dooley family and all who loved and shared so many epic moments with you. You will be missed. Peace be with you all.
Ron Johnson
March 2, 2022
Dear Dooley family, may God watch over all of you during these tough days.
John Geshkewich
March 2, 2022
Sorry for your loss. I wanted to offer my condolences.
Your family and Jimbo are in my prayers.
Sharon Delahanty
March 2, 2022
Dear Mary Ann, so sorry for your loss. Your family are in my thoughts & prayers.
Katie McCracken Moore
March 2, 2022
While back in the day we had no idea that SMH would become a common acronym (it is, I promise), `Shaking My Head´ should have Jimmy´s picture next to it in the finest book of acronyms. That kid had me SMH at every encounter, but with a smile on my face and a warmth in my heart. What a gem. RIP Jimmy. Sending love and prayers to all you Dooleys, from me and the McCracken family.
The Beam Family
March 1, 2022
We have been holding you close in our thoughts since hearing of your loss. We will remember him always.
Mary Jo (Roth) LoBianco
March 1, 2022
Very sorry to hear of Jimmy´s passing . The entire Dooley family is in my thoughts and prayers.
Ann (Scott) Torp
March 1, 2022
Dooley Family, this is such sad news. My heart goes out to all of you. I always enjoyed talking to Jimmy. He was taken too soon. Love and prayers.
Kathy and Joe Fivelson
March 1, 2022
Dear Dooley Family, our thoughts and prayers are with you. We are so very sorry for your loss.
Molly Burns
March 1, 2022
Our sympathy to your family... was so sad to see the Candlelite sign- Love to the Dooleys from thd Burns Harper family.
Sean Sullivan
March 1, 2022
I met James Simpson when he was about 4 when he came to an SMM football practice and I dressed him up in my shoulder pads and helmet (Jim was a big kid). He cracked up at my name and proceeded to call me Seen Seen Sulliveen from then on. Jim was a unique individual with his own take on life. Quite a literary minded sort of fellow. Quick and Smart. With his size and personality, you definitely knew when he arrived anywhere. A gentle, very funny giant. He will be absolutely much missed. God Bless All the Dooleys, especially his brilliant and beautiful Mother. You are in my and the Sullivan's prayers. Jim was the 'Goods'. Godspeed
Jim & Alida Nally & Family
March 1, 2022
Dear Dooleys,
Jimmy was full of knowledge, and full of fun. I always enjoyed our wide-ranging conversations. A kind soul, who made everyone feel included. He embodied the "Big Red" spirit.
Sincere condolences to you all.
Jim and Nancy Brennan
March 1, 2022
Ned, Mike, Rob and family, we offer our deepest heartfelt condolences to all that grieve for Jimbo. May he carry the laughter into heaven.
Liz Kearns (Wallace)
March 1, 2022
I´m sorry for your loss. Sending prayers for your family.
Paul Cassell
March 1, 2022
Ned, I wanted to offer my condolences regarding the loss of your brother. Stay close to family/friends during these difficult times.
Deke
March 1, 2022
I am so sorry for the loss of Jimmy, may god watch over him on this next journey

Adam Matanovic
March 1, 2022
I will miss Jim dearly. He was a great football coach to me when I played at SMM as a kid. He was a great motivator and he was tough as nails. He used to head butt me with my helmet on and he wasn´t wearing a helmet. Lol Jim was hilarious and witty! A very warm and kind person. I enjoyed our conversations very much. Jim was somewhat of a Rogers Park and Chicago historian. He knew so much about so many. The old neighborhood won´t the the same without him. I´m grateful for the memories I have to hold on to. No one can take those from me. Rest easy Jimbo! You certainly left your mark and touched many people. You will be very missed by so many.
Cole Hyland
March 1, 2022
Jim, I'm going to miss our decade+ long debate about Rogers Park boarders and conversations ranging from which Mexican restaurant had the best salsa to the cultural norms of EACH Northside Catholic parish, everytime I always learned something.
RIP "Sir Jimbo"

Dan (Danny) McGuire III
February 28, 2022
Dear Mary Ann, Rob, Mike, Ned, and Katie,
I received two early calls today from my Dad and my brother Mike notifying me of Jimmy's sudden passing. From that point forward my day has felt like is was walking in a deep fog coming off of Lake Michigan! I am so profoundly sorry for your loss of a great son, brother and kind soul!
There will be many stories told of Jimmy's kindness, his character, his ability to turn a phrase and his love of family and friends alike. During this difficult time I am remembering the joy that he spread, the kindness he shared, his zest for life and his unique laugh. I can still hear him saying "Hello Daniel Francis" when we saw each other at the St. MM Chuckwagon, downtown or in the neighborhood!!
May your grief be assuaged by thoughts of his smile, his passion, his sense of humor and the joy that he brought to so, so many through his all too short walk on Earth.
May God hold you all in the palm of his hand during these difficult times.
Love,
Dan "Danny" McGuire and Family
Brendan Cunningham
February 28, 2022
I worked with Jimbo on the cboe floor for years. What a great guy who made everyone laugh every chance he could. Condolences to his family and friends. RIP Jimbo
Mary Colleen Morsli
February 28, 2022
My heart is heavy. RIP, Jimbo.
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