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James Letizia Obituary
Waukesha - Born to Eternal life April 14, 2021 at the age of 68. Beloved soulmate of Susan Young for over 25 years. Loving father of Sharon (Kevin) Katzenberg, James T. "Turk" (Natalie) Letizia and Thomas J. (Kristie) Letizia & Curtis (Bonnie) Young. Dear grandpa "Papa Naughty" of Gavin Letizia and Sunny Lynn Letizia. Brother of Carl (Christa) Krieger, the late Thomas Letizia, Jr. and the late Frank Vert. Further survived by nieces and nephews and his beloved dogs Checkers, Smokey and Diesel.
Jim was a self made entrepreneur starting his car dealership legacy as the owner of Diamond Jim's Auto Sales in 1978 later adding Diamond Jim Motorcars. He then went on and created Diamond Investments in 1985, Diamond Jim's Sports Lounge in 1995, Diamond Jim's Stoneridge Inn in 2001, which is currently operating as Diamond Jim's Steakhouse and The Tower Restaurant and Bar in 2010.
As many know, Diamond Jim enjoyed racing on local dirt tracks with his son, Turk, for over 40 years. His racing career started at Hales Corners Speedway driving a Sportsman, Number 152. Diamond's race car number changed several times throughout his racing career. In 1993 Diamond bought his new teal GMC Dually that he used to tour many speedways in the midwest, with matching infamous teal colored race cars, and later the D7 Late Model became his famous and final number. Diamond's race cars truly represented who he was and the success he created throughout the years of his life. His love for racing went further as he sponsored several race teams in several divisions, Including "Diamond Jim night" at Hales Corners Speedway for many years, and Dirt King's "Diamond 40" events.
Jim still had time to enjoy fishing and waterskiing with his children, going to Nascar races and riding his Harley Davidson with his friends. He loved feeding the wildlife including birds, deer and other animals.
Jim was a man of many talents, he worked tirelessly around the clock to achieve and maintain his success, not only for himself, but for his entire family and for his friends. Jim would help anyone in need without hesitation.
A visitation to celebrate the life of Diamond Jim will be held at the Brookfield Convention Center 325 S. Moorland Rd. Brookfield, WI 53005 (262-789-0220) on Sunday April 25, 2021 from 1- 5 PM.
Diamond Jim
"Cadillac of Used Car Dealers"
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Memories and Condolences
for James Letizia
Sponsored by Max A. Sass & Sons Funeral and Cremation Service Westwood Chapel - Muskego.
George
April 11, 2025
Miss you brother
Linda Core
August 5, 2024
I know Jim passed away awhile back, but I just heard of this recently. My deepest condolences to his family. Jim and I attended school together from grade school through senior year at South Division H.S. in Milwaukee. I will always remember his great smile, and friendly demeanor. He definitely was 'one of a kind'. He used to give me rides to and from work when we were in high school and I will always remember his kindness. I'm sure he is sorely missed by his friends, family and business associates. Rest in peace my friend. You may be gone, but you will never be forgotten. Your friend, Linda (Ruszewski) Core, SDHS Class of 1971.
George Markopoulos
April 13, 2024
Miss you my dear dear friend
Mick Walsh
April 11, 2023
Prayers and best wishes for the family.
Karen Harrass
May 7, 2021
Sad, sad coincidence. Today I was looking for a place to eat on Mothers day. The first place I looked was Jim's restaurant.
My husband Steve, was in the car business for 40 years. He passed away in 2016. When "the boys" got together, the name Diamond would usually come up. I knew immediately who they were talking about.
For some reason today, I went on line looking at the fate of Cadillac dealerships. There were pictures of all kinds of Cadillacs, and a picture of a man. When I opened that picture up, it led me here to the obituary.
Jim came to mind for dinner on Sunday.
Within two hours I find he has passed away.
My condolences to the entire family. I did not know Jim personally, but he was still a part of my husband's life. Anything that was part of my husband's life, was part of my life as well. He will be missed.
"DIAMOND" you always had/have the best shrimp in Wisconsin!
Tom E. Eckert
April 29, 2021
Met Jimmy 1970 - great 67 GTO conv. A lot written about later years.
As a teen Jimmy worked at Crazy Jim's on S. 16th st. Jimmy lived like 3 house away.
He and Kenny worked at Metropolitan Cadillac. At night at their body shop on W. Pierice St. Moved the body shop to w. National ave next to his father's bar, Tommy's. Jimmy lived up stairs. Picked up my 1st Fleetwood from Jimmy who had to take the paperwork to the Met on Wis. Ave., where they still worked.
They moved to the Lincoln ave lot. Pretty sure the Met moved off Wis. Ave. and Diamond Jimmy got their old, super large sign, which is still there.
Trust me, Diamond was a self made man, but Crazy Jim Sr. was his inspiration. Crazy J. would drive into the lot and just sit there in his red Cadillac conv. Smoking his fat cigar. Niether would wave, or talk, etc. The two Jim's would just - be there in the moment. Crazy J. would project, you have a long ways to go to be me; and Diamond would say, "I'll be bigger than you!"
Crazy would sell a car for a 6 pack of Pabst Blue Ribbon - Diamond sold me a car for a Diamond ring. Crazy J. had the Demo Derby's at Hales Corners, Diamond raced in and later raced there under his own lot, etc. Crazy J. went into real estate and Diamond did too.
Someone posted Wally Rank? Maybe so, But I assume they meant Crazy Jim Sr. (Jaborn mes Groh), not his mentor, butmpre his early inspiration and motivator.
Diamond Jim and Crazy Jim were both great car dealers and Milwaukeeian's.
I sincerely hope to see them both in the Here-After.
TEE
Lynn and Alan Smolen
April 25, 2021
WE WERE FILLED WITH SORROW
FOR SUE AND THE FAMILY
WE WERE CUSTOMERS AT THE RESTAURANT AND WANT YOU TO KNOW HOW MUCH THE RESTAURANT AND SUE AND DIAMOND MENT TO US AS CUSTOMERS. WE ENJOYED EVERY SINGLE BITE!!!! THANK YOU FOR UNDERSTANDING FOOD AND BEVERAGE HE WILL BE VERY MUCH MISSED OUR SPECIAL THOUGHTS AND PRAYERS TO SUE
KNOW HE WILL BE WITH YOU IN YOUR HEART ALWAYS AND FOREVER!
Steve and Nicole Claflin
April 22, 2021
Diamond was an amazing person who lived life to the fullest. Our condolences to the entire family, you are all in our thoughts and prayers. RIP Diamond, you will be missed.
Gregg Fitzpatrick
April 22, 2021
In loving memory of a wonderful person. We will love you and miss you always. Gregg & Eddie.
Ken and Cheryl Jaeger
April 21, 2021
We were so sorry to hear about the passing of Diamond. Our sincere sympathy to Sue and the entire family,
Mary Winski
April 20, 2021
So very sorry Sue to hear of Diamond Jim´s passing. My thoughts are with you and his family.
Jane Lundy
April 20, 2021
So very saddened by the news. To young to leave this world. Susie and family, our prayers to keep you in God's loving hands. Jane n Ron
Ralph & Donna Machowski
April 20, 2021
Sue and family Ralph and I were so very sorry to read of Jim`s passing
Far to young of a age Blessing to your entire family
Josh Swan
April 20, 2021
I got to meet Jim and his wife once at Kelly's Bleachers in Big Bend a few years ago. I didn't know who he was until I saw his Diamond Jim shirt and then he told me who he was. Jim couldn't get his motorcycle started because the battery in his key fob was dead. So I offered to drive him and his wife home. I drove them home in my 1979 Volare wagon and he talked about how he used to sell these cars when he first started out. He seemed like a great person based on this one moment I had with him. He found it necessary to give me $20 for the ride home. He left a small black pocket knife on the dashboard of my Volare. It is still sitting in the same spot he left it. I doubt this little pocket knife has any special meaning to the family but if it does I do have it and would be willing to meet up and give it back to the family.
pete tisonik
April 19, 2021
sorry to hear of jim leaving us so soon. bought my first used cadillac from him when he had a little lot on forest home aveenue. bought 3 more from him since then. my sympathy to turk and the family. jim is probably riding around with wally rank in a big eldorado rag top right now.
Andy and Donna Laird
April 19, 2021
R.I.P. Diamond
Gone way too soon
Andy and Donna Laird
April 19, 2021
Andy and Donna Laird
Dan and Charlene Goben
April 19, 2021
Glad to be a part of the Family and to have known such a Wonderful Man
Kathy Jorgensen
April 18, 2021
Offering my prayers to the family. I grew up during the Diamond Jim era and have fond memories of his legacy. RIP JIM
Asta Harmon
April 18, 2021
My deepest sympathy goes to Tom, Turk and entire family. Diamond Jim was respected by everyone whoever had an opportunity to meet him. I know his legacy will continue on and memories will be cherished forever. Please accept my heartfelt condolence of your father´s death.
Betty Watson
April 18, 2021
My sympathy to the family. No one will ever forget those teal colored race cars. Wish to thank Jim for all the business he did with my son. It certainly helped him with his racing career. He´ll be watching over you from above.
John &Karen Strobel
April 18, 2021
Our deepest sympathy..Love and prayers are with You and the family.
Liz Henry
April 18, 2021
My heart hurts at this news. Having worked at the car lots for so many years, one thing was certain, we were all family. Diamond was a great man. Many many hugs to you all.
Mick and Aruna
April 18, 2021
Sincere condolences to the entire family. Our thoughts and prayers are with you.
Andy and Donna Laird
April 17, 2021
Our sincere Deepest Sympathy to Everyone .
We have fond cherish memories of Diamond .
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