Tribute To Billy O’Toole Of “Families Of The Mafia” From Staten Island – Conversation With Children, Widow


Billy O’ Toole: A Rugged, Respectable Blessing

Written By: Cindy Mich

In the thirty-five years I have been a writer, this serves as my first written tribute, and in my own print publication. Those closest to me would mention that I am huge on honoring lost lives. The soul I speak of is someone I shall never get to greet or gather with, as he passed on in 2020. I cannot call upon him to vocalize his viewpoints, and lack  learning of any vehemence felt for his family or friends. 


I was left to formulate a credible commendation of this  fellow through television clips and telephone conversations; articles and personal assessments. Once the time came to create this article, I found myself both unsettled and unhappy that I would never meet the man they call Billy  O’Toole. 


Many recognize Mr. O’Toole from his participation on the MTV show Families Of The Mafia, or via his father’s intermingling with the Irish mafia. I was awarded a small window into his private side, and felt sincerely obligated to show the world he was larger than any one label. 


His sententious essence left an eternal indentation on  individuals afar and around the corner. Billy, you live on through your loves, and hopefully, within my words. As a rigidly intense reporter, it can be baffling to come up empty while digging up details on any subject. I ran myself ragged searching for set facts, so let me start off by saying a ton of thank you’s to Billy’s family for filling in all the blanks.      

Billy Cast, as he was called, had been brought up in Park Slope, Brooklyn. His rearing as a child was rough, leading  him to be insatiably smitten with the streets. His best friends were often times legal battles, booze, and large lapses  from being home. 


I do not mention these shortcomings to be saucy, but more so as a means for audiences to  understand his absolute makeup. When one stems from violence and volatility, their transformation is often ripe with  regret, torment, and mental torture. 


Such seems to be the truth for Billy. His internal scars seemed to bleed out and bubble over to those he deemed dearest to him. He was not intentionally iron hearted to other humans, rather, he became enslaved to his own habits. His search for a better self slipped farther from him through various falls. 

What Billy never seemed to see was that the best of him lie hidden under sadness and shame. By finally securing self-forgiveness, it enabled him to establish better relationships and beneficial resolutions for himself. Billy would, over a span of a significant number of years, build two families and hold two brides. 


He brought to the world a cluster of  children who, in many ways, mirror him. As stated by me to his magnificent bloodline, I am only but a petite vessel to pencil Billy’s persona to the population. Now that I was able to assimilate my impressions, his relatives shall now reveal their thoughts to YOU. 


I was offered the opportunity to speak with his former wife, Jessica Clare, and their three children: Matthew, Joe and Taylor. Their responses and reflections reiterate my suspicions about our main subject. Billy was a rabble rouser and a risk taker; a hero and a warm heart. Overall, a particularly precious person.


I am leading off with Taylor, who holds the huge honor of being named Billy’s “Baby Girl”, even though she is  twenty-three and engaged. Currently a Cosmetology student, she shared with me her hopes of one day working in  Manhattan at the completion of college. It is obvious by observation that Taylor held a menagerie of mixed feelings  about her father. 


You see her natural yearning to be nurtured by dad, yet Taylor did not immediately yield to Billy’s  necessities. Eventually, by his aeonian attempts to dilute their divide – he earned Taylor’s attention and appreciation.  She described her dad as a humorous, yet hot-headed man who was one hundred percent old-school. Her heart said  to me that Billy was what she never knew she would need nearly as much until his absence. I see this young lady  keeping him alive through her own sense of strength (which Taylor admits is from both her parents) and innate sense of independence. Furthermore, her tattoo reads “Beauty Lies Within The Heart”. It gives me goosebumps to say life does imitate art – Billy’s body may have departed, but his best remains safely inside her and her heart. 


Twin number two is Joe, and in large part, he parallels his padre in physical looks. The deep eyes and dimples; a bit of the bad boy attributes. Similar to his sister, he has found himself now engaged to the mother of his children, and  she is a gift, he says. As a parent myself, it is touching to witness how he looks at both his parents with extreme exaltation. He honors Billy as strongly for his shortcomings as his successes. His bull-headed behavior funnels to him in part from his father, but both grew from their gut wrenching worries. Joe classified Billy as a great guy who  taught him how to see his finest side, and how to fight his more ferocious sides. Sadly, the last time the two were together found them fighting. Joe, with all my heart, I am assured that your father will remember only your most remarkable mannerisms. Parents eternally cherish their children. 


On to twenty-five year old Matthew, who was seen only slightly on Families Of The Mafia. He happens to be the calm and collected child, but does possess a protective personality. Matthew tends to believe that the toughest battles  we have are in one’s own head. Wickedly wise wisdom from this young man. Billy was his super hero, and he was truly thankful for the ten years he had spent with him. His father’s wants and needs were supremely symbolic to  Matthew. However, I will allow his wistfully written tribute to speak for itself (see below). 


Last but not least, we have Jessica, aka the prior Mrs. O’Toole and at present, “Meme”. Ms. Clare is mother to five children; grandmother to three little tots. So not shocking to discover that she and Billy were identical in infinite ways. Both came from cumbersome childhoods in Brooklyn. Each were on an eternal search for security and true love. In the absence of the aforementioned, you overcompensate by constantly searching for safety and always loving harder. 


Billy and Jessica both loved their dogs deeply and got to the gym almost daily. Passion was also never a problem for either party. The only true difference was in their eventual roles within the world. Billy became invisible for some time, and Jessica stayed and served as the solid family rock. Throughout their thirty years of love for each  other, there were numerous fights yet fondness; setbacks followed by sweetness. 


She gladly emphasized that Billy  held a great heart and always fought hard to honor his own beliefs. She never spoke ill of him to their children, nor discouraged reunions or reconciliations. In her words, his death was her heartbreak. No passing nor person could, nor can, stop the love and loyalty between these two beaus. 

I comprehend that no written testament can truly capture any person as a whole. My hope in doing this tribute was to accomplish three things. For one, to help his family and friends feel closer to him as they push closer to peace. Secondly, for strangers to gain an appreciation for this significant soul. Thirdly, so that, for as long as our species is  in existence, Billy O’Toole has now been immortalized both on and off screen. I so hope I succeeded. 

To conclude, Billy, thank you for letting me shine a light of love on you and yours. I pray you are resting well among  the angels, and smile down daily on your pack with pride. B.O.T. was the best.  


Cindy Mich

Cindy Mich is an award-winning journalist/media personality who is also a filmmaker and Founder of the independent film festival, Art is Alive, now in its seventh year. Her total listening audience is at 205,000 to date. In print, she currently contributes to various digital publications, along with having owned and operated her own publication, The Art is Alive Magazine. After eight issues, her readership was at 78,000. She performs the duties of a professional film judge, having screened over 800 films in the last few years - along with covering various film festivals as accredited media. Further, she has taught in both the public and private sector. In 2023, Cindy is adding a distribution arm to her film festival, and soon will be releasing her made for television series on medical misdiagnosis, Hurt by Healthcare.

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