Remember

Leonard "Lenny" Tomaiolo, Jr.

October 2, 1963 - May 11, 2011
Shrewsbury, Massachusetts

Set a Reminder for the Anniversary
of Leonard's Passing

Pause Days Gone By by Bruce H. Zimmerman (ASCAP)

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Message from the Family

Thank you for your support during this difficult time. We love Lenny and will miss him so very much. Please add to this tribute to Lenny by adding your memories and photos.

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Heald & Chiampa Funeral Directors

5 Church Road
Shrewsbury, MA 01545
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Memories & Candles

“uncle Len, i am up missing you a lot tonight. I wish you would just come back home. Your we're such a great man, and all i can do is look at pictures...Read More » ”
1 of 55 | Posted by: Christina Litchfield - Niece

“Happy Birthday Len, from your favorite father-in-law. You are in my prayers EVERY night. May you be resting in peace. ”
2 of 55 | Posted by: Dick Joseph - Shrewsbury, MA

“Hi Angels. It's just Uncle Mick thinking of you. I visit this site often and say a little prayer. Dad's watching over you ALWAYS. xoxo ”
3 of 55 | Posted by: Uncle Mick - Shrewsbiry, MA

“Dear Wendy- My gosh, it's been years and years since I've seen you or Lenny. I knew Lenny, as a child, growing up in our neighborhood. He was a...Read More » ”
4 of 55 | Posted by: Linda Duprey - York , ME

“Dear Wendy, I am so sorry for you and your daughters' loss. My heart goes out to you and your family. Please know that I;m here if you ever want to...Read More » ”
5 of 55 | Posted by: Pat Samoluk - Sandwich, MA

“HEY WENDI, LINDSEY AND LACEY, WE WILL MISS LENNY'S SMILE, JOKES AND HUMOR. ALL THE TIMES HE CAME TO AGWAY TO TELL US STORIES, ALWAYS BRINGING...Read More » ”
6 of 55 | Posted by: DAVE ZECCO AND LISA FOX - MA

“Dear Wendy may this candle I lit stay bright & serve as a light in your heart & soul to always let U see the path & guidence & to show U the road...Read More » ”
7 of 55 | Posted by: Karyn R Plaud ( Rosy ) - FRIEND

“Rest in peace my childhood buddy. Jim McKiernan ”
8 of 55 | Posted by: Dr. James V. McKiernan

“I am so sorry for your loss and my thoughts and prayers are with you all at this time. the picture on this page says a thousand words but only one...Read More » ”
9 of 55 | Posted by: Pete cosenza jr. - friend/barber

“My heart, prayers and blessings go out to Lenny's family. I worked with Lenny at the dealership, and knew him to be a great guy with a wonderful...Read More » ”
10 of 55 | Posted by: Bob Hinchey - E Falmouth, MA

“Cuzzy, you have a heart of gold. You brought me into your home and your family when I was down. Your beautiful children call me Uncle. Thank you. I...Read More » ”
11 of 55 | Posted by: Uncle Mick - Friend

“Lenny - a cohort in the automobile business, a partner on the golf course and most of all a great friend. I'll miss your sense of humor, your many...Read More » ”
12 of 55 | Posted by: Theodore Budzyna - E. Dennis, MA

“Smoochie , you were one of a kind my friend! I am truly blessed to have known you like I do. Thank you for sharing your beautiful family and your...Read More » ”
13 of 55 | Posted by: David Marcoux ( Pickle ) - MA

“My thoughts and prayers are with your family. ”
14 of 55 | Posted by: Allison Figueras-Smith

“Love you! <3 ”
15 of 55 | Posted by: Lindsey Tomaiolo - Daughter

“We are so sorry for your loss and our thoughts and prayers are with you all at this time. We are still in Florida and will be unable to be there. I...Read More » ”
16 of 55 | Posted by: Romeo & Annette Turo - Cousin

“Lindsey, Lacey and Wendy: No words will ever comfort you in your loss and these difficult times ahead. My heart is truly broken for you girls and...Read More » ”
17 of 55 | Posted by: Marino Jollette - Step Brother

“I'm so sorry for your loss. From what i learned in the last few years of Lenny, he was an awesome dad and loved his family (and golf). He is forever...Read More » ”
18 of 55 | Posted by: Lisette Williams - Tampa, FL

“Wendy, Maureen, myself and the kids send our deepest sympathy to you and the girls. You are in our thoughts and prayers. Steve Power ”
19 of 55 | Posted by: Steve Power - Shrewsbury, MA

“Dear Wendy, Lindsey, Lacey, Richie, Dick, & Elaine ~ I am so very sorry to hear of your loss. May the support & strength of your wonderful family ...Read More » ”
20 of 55 | Posted by: Mrs. Laura Jonaitis

“Wendy, There are no words. You will remain in my thoughts 24/7 over the weeks and months to come. Please know how loved you are. Paul ”
21 of 55 | Posted by: Paul Campaniello - Shrewsbury, MA

“Best Dad ever. I love you so much and you mean so much to me. I love you dad <3 ”
22 of 55 | Posted by: Lacey Tomaiolo - Shrewsbury, MA

“I would like to express my deepest sympathy to Lenny's family. I am deeply sorry for the loss of an exceptional family member coming from an...Read More » ”
23 of 55 | Posted by: Linda Mesolella Drapeau

“Wendy, Lindsey and Lacey, Our deepest sympathies to you and your families at this tragic time. Please know you are in The Dean-Carskaddan family's...Read More » ”
24 of 55 | Posted by: Barb Dean Carskaddan

“Wendy, Lindsey, Lacey and the Tomaiolo Family, Our heartfelt condolences to you for the loss of Lenny. Our thoughts and prayers are with you. ...Read More » ”
25 of 55 | Posted by: John '79, Sheryl and Jillian Barry - MA

“Dear Wendy and Girls, You are in our constant thought, our hearts are crushed. David and I will never forget the love you and Lenny shared at...Read More » ”
26 of 55 | Posted by: Chrissy and David Webster - MA

“Dear Wendy, Lindsey and Lacey, He was like a son and will be forever in my heart. Love, Auntie Em ”
27 of 55 | Posted by: Marilyn Frey - Friend

“To Lenny's Family- Please accept my deepest sympathy... may the fond memories you will always have help you through this difficult time. ...Read More » ”
28 of 55 | Posted by: Lisa Marcello - West Boylston, MA

“Our hearts ache for all of you. Our love, thoughts and prayers for you, and may God give you the strength that you need. Our deepest sympathys, ...Read More » ”
29 of 55 | Posted by: kim catalina - worcester, MA

“Sorry to hear of your loss. Lenny was a great guy and left us to early. ”
30 of 55 | Posted by: Billy McManus - Davidson, NC

“Wendy I cannot express my shock & sorrow to learn of Lenny's passing. Any words that I might write cannot do justice to your loss. Please know that...Read More » ”
31 of 55 | Posted by: Tom Borge - Sterling, MA

“I am absolutely stunned to hear this tragic news. My thoughts and prayers go out to Wendy and the girls as well as Amy and Len and the extended...Read More » ”
32 of 55 | Posted by: Rhonda - West Boylston, MA

“Lenny will be missed. Never a dull moment. God bless you and you family in these trying times. You will remain in my prayers. ”
33 of 55 | Posted by: Bill Trottier - Friend/co worker

“My Dearest Wendy, Lindsey and Lacy, Words can not express the sadness I felt when I heard the news. May the wonderful memories of "Lenny" .....Read More » ”
34 of 55 | Posted by: Susan Simone - shrewsbury, MA

“Wendy I had the best time with you and cuz last Saturday night!!! Singing and dancing like old times! I'm so glad you guys came by I will never...Read More » ”
35 of 55 | Posted by: Marc Turo - Northborough, MA

“To all the Tomaiolo and Joseph famiy members, I am SO sorry and heartbroken for your loss. Our whole family sends their thoughts and prayers to you...Read More » ”
36 of 55 | Posted by: Anne Donovan Matthews - MA

“Wendy, Lacey and Lindsey, Nicole and I are so very saddened by this loss, and we have you in our thoughts and prayers during this trying and...Read More » ”
37 of 55 | Posted by: Jon Rawson - Worcester, MA

“Ner, You are the best. I have been thinking about all those times you have made us laugh so hard. Because of you everyone goes by "George" or ...Read More » ”
38 of 55 | Posted by: Jason & Kristin St. Pierre - MA

“Dear Wendy, Lindsey and Lacey, Thank you for sharing Lenny with us. he was a great boss and a great person. He will...Read More » ”
39 of 55 | Posted by: michael richard - fitchburg, MA

“George, I don't even know what to say! You were always there for me. You were the brother I never had...an irreplaceable bond! There won't be a...Read More » ”
40 of 55 | Posted by: Matthew Tomaiolo - Boylston, MA

“Dear Wendy, children and Elaine and Dick, We are sorry for your loss and you will be in our thoughts and prayers at this very difficult time. ”
41 of 55 | Posted by: Sharon Thomas - Friend

“I love you dad forever and ever. <3 RIP ners. ”
42 of 55 | Posted by: Lindsey Tomaiolo - MA - Daughter

“Dear Wendy, Lindsey and Lacey, We are so saddened to hear the news about your loving husband and dad. Our hearts ache for all of you. Just know...Read More » ”
43 of 55 | Posted by: Janet Lavine - westborough, MA

“TO THE FAMILIES OF LENNY, WE GRIEVE WITH YOU FOR THIS TRAGIC LOSS. OUR PRAYERS ARE WITH YOU. GOD BLESS! ”
44 of 55 | Posted by: bob and barbara ovanes - jupiter, FL

“Wendy, Rich, Mr. and Mrs. Joseph I am so sorry for your loss. My heart goes out to Wen and the kids. You were my second family growing up and I...Read More » ”
45 of 55 | Posted by: Mark Campaniello - Shrewsbury, MA

“Lenny you were one-of-akind! Always knew how to make us girls smile at Tomaiolo's in the middle of a deep dinner rush. Definitely true to say that...Read More » ”
46 of 55 | Posted by: Katie Heald - friend

“Wendy, Lindsey & Lacey I am so very saddened by your loss i knew Lenny for over 16 years first met him when he came in to our delership as a...Read More » ”
47 of 55 | Posted by: Silvio Ruisi - Newton, MA

“I am so sorry for your loss, Lenny and I worked together at Wayside Ford, Im going to miss the morning meetings and jokes we shared, Lenny was...Read More » ”
48 of 55 | Posted by: Steve Christie - Hudson, MA

“Wendy, words cant express how terribly sorry I am for your loss. Lenny was like a brother to me and I will miss him so much. God bless you and...Read More » ”
49 of 55 | Posted by: Nick Simonetti - Lynnfield, MA

“Wendy, It is hard to believe and crushing news to know that you have lost Lenny. In this sad and difficult time, let me add my condolences to all...Read More » ”
50 of 55 | Posted by: Bradford Kellogg - Fitchburg, MA

“Hi Wendy, Words can't quite express just what we're feeling for you and the family right now. We're so, so sorry for your loss. Lenny was an...Read More » ”
51 of 55 | Posted by: The Levine Family - Steve, Jamie, Sam, Jesse and Daniel - MA

“Dear Wendy, This is stunning news. I am so sorry for you and the girls. Please know we (your ViewLogic clan) are here for you. With deepest sympathy,...Read More » ”
52 of 55 | Posted by: Leigh Horte - West Groton, MA

“I am sorry to hear of your families loss. I worked with Lenny years ago at Harr Ford. To date he was one of the funniest and best managers I ever...Read More » ”
53 of 55 | Posted by: Stephanie Eco - Northborough, MA

“Dear Wendy, Lindsey & Lacey, There are just no words to express how sorry I am for your loss. My heart is just breaking for you. Please know...Read More » ”
54 of 55 | Posted by: Shelly Keene - Shrewsbury, MA

“I am so terribly sorry for your loss. ”
55 of 55 | Posted by: Jill Coran - family friend

View Life Images Slideshow →

Mr. Leonard F. Tomaiolo Jr., of Shrewsbury, died unexpectedly, Wednesday, May 11, 2011, at the family home in Mashpee. "Lenny" was born October 2, 1963 in Worcester. He was 47 years old.

Lenny was a graduate of St. John's High School, class of 1981. With an affinity and knowledge for automobiles he was owner and president of L.A. Brokers, a car wholesaling business for over 10 years. Presently, he was General Sales Manager for Wayside Ford in Marlborough. He was top-notch in the automobile industry.

Away from work, his passions and interests varied but ranked among the top was golf. His career highlight came last year when playing in the Northborough Lions Tournament at Mt. Pleasant Country Club in Boylston. He sank a 52 foot putt and won a $10,000 prize. Rightfully so he boasted to all family and friends. Lenny is described as a man with a heart of gold who had an ability to make everyone laugh and be comfortable. He treasured his time spent with family on Cape Cod, fishing and on his boat. He was a talented cook and true to his Italian heritage, Lenny could serve many dishes that became his signature specialties. But in the end what mattered most to Lenny was the love he had for his family. His wife, daughters and extended family brought him immeasurable happiness that he now takes with him on the next part of his journey.

On September 5, 1993 he married Wendy A. Joseph at St. Rose of Lima Church in Northborough. She coined him with the nickname "George" and it remained with them forever.

In addition to his wife of 18 years, Wendy A. (Joseph) Tomaiolo, he leaves two daughters, Lindsey A. and Lacey A. Tomaiolo, all at home; his father and stepmother, Leonard F. Sr., and Amy A. (Palermo) Tomaiolo of Shrewsbury; his mother, Kari (Hansen) Tomaiolo of Boylston; his sisters, Lucia O'Keefe and her husband, James, of Fort Lauderdale, Florida and Gina M. Litchfield and her husband, Richard, of Shrewsbury; his paternal grandmother, Louise (Aspero) Tomaiolo of Shrewsbury; his in-laws, Richard N. and Elaine E. (Massad) Joseph of Shrewsbury; brother-in-law, Richard N. and his wife, Mary Anne (Kocot) Joseph; his cousin whom he considered a brother, Matthew F. Tomaiolo and his wife, Robin (Pacheco) Tomaiolo, of Boylston; aunts and uncles, including Frank Tomaiolo, whom he considered his second father, and his wife, June (Kelleher) Tomaiolo of Shrewsbury; nieces, nephews, cousins and a host of friends.

Family and friends will honor and remember Lenny's life by gathering for calling hours at Heald & Chiampa Funeral Directors ~ The Sumner House, 5 Church Road, On the Common, Shrewsbury Center on Sunday from 2 to 6 p.m. and again at 8:45 a.m. on Monday morning before leaving in procession to Saint Mary's Church, 640 Main Street, Shrewsbury, where his Funeral Mass will be celebrated at 10:00 a.m. Burial will be in Mountain View Cemetery.

Friends who wish to honor Lenny's memory may contribute to The Tomaiolo Children's Education Fund, in c/o Shrewsbury Credit Union, 615 Main Street, Shrewsbury, 01545.

Funeral Services

Interment

Mountain View Cemetery

Boyslton Street (Rt. 140) Shrewsbury, MA 01545

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Visitation

May 15, 2011
2:00 PM to 6:00 PM

Heald & Chiampa Funeral Directors - The Sumner House
5 Church Road
Shrewsbury, MA 01545
508.842.3700

Get Directions

Funeral Mass

May 16, 2011
10:00 AM

Saint Mary's Church
640 Main Street
Shrewsbury, MA 01545

Get Directions

Interment

Mountain View Cemetery
Boyslton Street (Rt. 140)
Shrewsbury, MA 01545

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Memories & Candles

Page: 1 of 6

View All View Candles

uncle Len, i am up missing you a lot tonight. I wish you would just come back home. Your we're such a great man, and all i can do is look at pictures, smile and cry a little bit. Just know i am always going to have you in my heart<3 love you i>

Posted by: Christina Litchfield - Niece Jan 22, 2013

Happy Birthday Len, from your favorite father-in-law. You are in my prayers EVERY night. May you be resting in peace.

Posted by: Dick Joseph - Shrewsbury, MA - Father-in- Law Oct 02, 2012

Hi Angels. It's just Uncle Mick thinking of you. I visit this site often and say a little prayer. Dad's watching over you ALWAYS. xoxo

Posted by: Uncle Mick - Shrewsbiry, MA - Uncle Dec 28, 2011

Dear Wendy-

My gosh, it's been years and years since I've seen you or Lenny. I knew Lenny, as a child, growing up in our neighborhood. He was a big personality. A novelty.
Your family photos are a true testement to your love and happy lives together. My prayers and thoughts go out to you and your girls.

Peace,
Lnda Duprey Briggs

Posted by: Linda Duprey - York , ME - childhood friend Jul 11, 2011

Dear Wendy,
I am so sorry for you and your daughters' loss.
My heart goes out to you and your family. Please know that I;m here if you ever want to talk.
Pat Samoluk

Posted by: Pat Samoluk - Sandwich, MA - friend/peer Jun 18, 2011

HEY WENDI, LINDSEY AND LACEY,
WE WILL MISS LENNY'S SMILE, JOKES AND HUMOR. ALL THE TIMES HE CAME TO AGWAY TO TELL US STORIES, ALWAYS BRINGING A SMILE AND LAUGHTER TO ALL OF US. WE WILL MISS HIS PRESENCE AT THE GOLF TOURNY THIS YEAR VERY MUCH. HIS HOLE IN ONE WAS SO AMAZING. WE WILL DEDICATE OUR FIRST HOLE "TEE" SHOT TO HIM IN HIS HONOR. PETER, DAVE, ERIC AND MYSELF WILL USE HIS TEES AND SEND OUR BALLS

... more

Posted by: DAVE ZECCO AND LISA FOX - NORTHBORO, MA - FRIIENDS May 17, 2011

Dear Wendy may this candle I lit stay bright & serve as a light in your heart & soul to always let U see the path & guidence & to show U the road to rest of the way thru your life & 2 bring U 2 peace & happiness & 2 always see Lenny directing U down that Road for U & the girls <3 sorry again><3><3><3><3>

Posted by: Karyn R Plaud ( Rosy ) - FRIEND May 17, 2011

Rest in peace my childhood buddy. Jim McKiernan

Posted by: Dr. James V. McKiernan - childhood friend May 17, 2011

I am so sorry for your loss and my thoughts and prayers are with you all at this time. the picture on this page says a thousand words but only one comes to mind, That's Lenny! i will miss all the conversations and laughs at my barber shop. every time i seen Lenny he made me laugh. and as for a hard day a lot more enjoyable and i will miss our time together.

Posted by: Pete cosenza jr. - friend/barber May 15, 2011

My heart, prayers and blessings go out to Lenny's family. I worked with Lenny at the dealership, and knew him to be a great guy with a wonderful sense of humor, along with great product knowledge. He will be dearly missed

Posted by: Bob Hinchey - E Falmouth, MA - co-worker May 15, 2011

Page: 1 of 6

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Life Stories provides friends and families a forum to post their favorite stories and memories of Leonard "Lenny" Tomaiolo, Jr. ensuring the precious experiences are never forgotten. Share joyful times, post a photo that captures the moments you cherish, and allow others to reply, relive and remember.

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lenny always called me cousin and i gave him the nick name left side plus in the wholesale car world thats always wanting the high end and then some for his used wholesale vehicles. we always made each other laugh even with just a look i will miss him .tom (frat) fratantuono FRATS AUTO BROKERS INC.

Posted by TOM (FRAT) FRATANTUONO from foster, RI - friend on
May 13, 2011

Leonard "Lenny" Tomaiolo, Jr.

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