Episodes

  • 471: Massapequa Board Candidate Cheryl Lepre
    May 11 2026

    Comedian and podcast host Tom Kelly continues his Massapequa School Board interview series with current board member and candidate Cheryl Lepre. - Recorded at Paradise Studios in Massapequa, Long Island, this long-form conversation covers: - The "Save the Chief" lawsuit Taxpayer money and school budgets COVID and mask policy fallout Anonymous Facebook politics Transgender locker room controversy Universal Pre-K Education, AI & vocational training Why Massapequa has become a national political flashpoint And whether local politics has become too mean This episode focuses heavily on tone, community identity, and what Cheryl Lepre believes keeps Massapequa schools successful. - ⏱️ TIMESTAMPS 1:19 – "Anyone who runs for school board is either crazy or a career politician" 1:41 – Cheryl explains her 7 years on the school board 1:58 – Why she continues to run for reelection 2:15 – PTA volunteer work & helping Boy Scouts become Eagle Scouts 2:43 – Tom asks if national politics have taken over local school boards 🪶 SAVE THE CHIEF & THE LAWSUIT 3:18 – Tom introduces the "Save the Chief" issue 3:39 – Why the school board is fighting to keep the Massapequa Chiefs mascot 3:48 – Cheryl discusses taxpayer money and fiscal responsibility 4:37 – Why she believes the lawsuit is financially worth pursuing 6:14 – Cheryl discusses conversations with the Shinnecock Nation 6:46 – NAGA (Native American Guardians Association) visits Massapequa 7:07 – "They prefer to be called American Indians" 7:54 – "Educate, not eradicate" 9:45 – Comparisons to Vikings, Crusaders & Spartans 10:17 – Lawsuit costs discussed: "0.08% of the budget" 😷 COVID, MASKS & POLITICAL DIVISION 12:11 – Tom compliments Cheryl's tone and communication style 13:01 – Cheryl compares this election cycle to previous campaigns 13:27 – Massive voter turnout during COVID-era elections 14:16 – Anonymous Facebook groups & online negativity 15:10 – Cheryl discusses avoiding toxic online comments for mental health 15:29 – Tom brings up Bobby Bonett's leaked COVID email controversy 16:19 – Cheryl clarifies the school board did not leak the email 16:55 – Cheryl explains FOIL requests and redactions 🚻 TRANS POLICIES & LOCKER ROOM LAWSUIT 19:32 – Massapequa lawsuits involving masks, mascots & bathrooms 20:01 – Cheryl says the district did NOT initiate the transgender lawsuit 20:23 – Tom summarizes the locker room controversy 20:32 – Cheryl explains the district policy 20:51 – Tom asks about rescinding the policy 21:03 – Cheryl says lawyers advised caution discussing the active lawsuit 21:18 – "We've made every accommodation for all students" 21:34 – Gender-neutral locker rooms and bathrooms explained 21:49 – Tom argues lawsuits distract from educational issues 22:01 – Cheryl describes school board presentations being overshadowed by controversy 22:29 – Career fairs, arts, athletics & student accomplishments discussed 22:43 – Why Cheryl believes opponents focus on lawsuits 🗳️ THE ELECTION & LOCAL POLITICS 22:57 – Tom asks about Bobby Bonett personally 23:12 – Cheryl calls Bobby "well spoken" 23:17 – Tom jokingly asks if Bobby is funded by George Soros 23:43 – Discussion of political ambitions in local elections 23:51 – Would Cheryl ever run for higher office? 🏫 EDUCATION, PRE-K & THE FUTURE 24:14 – Tom pivots the conversation toward education 24:19 – Cheryl reveals she now works in education administration 24:52 – Cheryl explains her work with special education placements 25:10 – Universal Pre-K debate begins 25:32 – "We're not against UPK — the question is sustainability" 27:01 – How the state funds UPK students 27:27 – State funding increases may change future plans 27:47 – Faith-based preschool concerns discussed 28:17 – Cheryl says the district is open to revisiting UPK 🎓 EDUCATION, AI & CAREERS 33:06 – Cheryl describes long board meetings and behind-the-scenes work ⚽ SPORTS, COMMON CORE & TESTING 33:36 – Questions from the "Massapequa Matters" Facebook groups 33:41 – Sports participation policy discussion 34:00 – Common Core and state testing debate begins 34:35 – Teacher evaluations and testing pressure discussed 35:01 – Why Cheryl believes some form of testing is necessary 35:21 – New York's changing Regents requirements 🏡 MASSAPEQUA IDENTITY & REAL ESTATE 35:35 – "People move here because they love Massapequa" 35:55 – Tom asks if the town is changing culturally 36:16 – Real estate prices exploding across Long Island 36:40 – Houses selling for tens of thousands over asking price 37:06 – Cheryl argues people move to Massapequa because of its traditions and schools 37:27 – "There's a reason people chose to move here"

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    40 mins
  • 470: Massapequa School Board Candidate - Danielle Ocuto
    May 6 2026

    Current Massapequa school board member and candidate Danielle Ocuto joins Tom at Paradise Studios in Massapequa for a wide-ranging discussion about: The "Save the Chief" mascot controversy Lawsuits and taxpayer money COVID-era mask debates Parent rights in schools Transgender bathroom and locker room policies Public comment at school board meetings Universal Pre-K And why local school board politics have become national news ⚠️ This episode is presented as a conversation and not an endorsement of any candidate or position. -------- Want To Record A Podcast Or Learn To Podcast? Recorded at Paradise Studios Massapequa - New York https://www.paradisestudiosny.com ----- ⏱️ TIMESTAMPS 1:00 – "National politics are Massapequa politics now" 1:20 – Is the election closer than it appears online? 1:37 – "You have to be insane to run for school board" 2:16 – Danielle Ocuto explains why she first decided to run 2:31 – Volunteer work, Girl Scouts & PTA involvement 3:14 – Growing up in Massapequa 🪶 SAVE THE CHIEF CONTROVERSY 3:44 – Tom asks about "Save the Chief" 3:59 – Danielle explains the mascot debate 4:22 – Kathy Hochul's mandate explained 4:30 – Why Massapequa became the district leading the lawsuit 5:10 – Fighting Irish vs Vikings vs Chiefs 5:36 – The financial side of replacing the mascot 7:08 – Tom shares his thoughts on the mascot debate 7:53 – Discussion about Native American outreach 💰 LAWSUITS & TAXPAYER MONEY 9:48 – "How much are we willing to spend?" 10:07 – Danielle pushes back on the $600K figure 10:49 – COVID-related lawsuits included in the total 11:15 – Breaking down the district budget 11:51 – Is there a cap on "Saving the Chief" legal spending? 😷 COVID, MASKS & SCHOOL BOARD POLITICS 12:07 – Cuomo, masks & hindsight 12:33 – "Maybe Massapequa wasn't so outlandish" 13:13 – Tom talks about how COVID changed his career 13:48 – Should school boards take political positions? 14:14 – Danielle discusses student safety and emotional wellbeing 14:41 – "Our kids were exploited during COVID" 15:17 – Why Danielle admired the school board during that time 15:35 – How COVID influenced her decision to run 📧 THE BOBBY BONETT EMAIL CONTROVERSY 15:51 – Tom reads Bobby Bonett's old COVID email on-air 16:52 – "Lowest common denominator of intelligence" becomes a meme 17:06 – Should school boards fight state policy? 17:50 – What about parents who disagreed? 🚻 TRANS POLICIES & BATHROOMS 18:35 – Parent rights discussion begins 19:06 – Schools not informing parents about gender identity changes 19:43 – Danielle explains state guidance on gender identity 20:22 – "Keeping parents out is not fair" 20:45 – Tom asks about the bathroom lawsuit 21:03 – "We don't want to hurt any students" 21:27 – Biological sex vs gender identity policy explained 22:20 – Who sued who? 23:02 – Federal vs state guidance conflict 23:35 – Gender-neutral spaces & accommodations 24:14 – Tom asks about Bobby Bonett's "changing booths" idea 24:29 – Danielle responds to the proposal 🎤 SCHOOL BOARD MEETINGS & LOCAL CHAOS 25:10 – Facebook groups & public outrage 25:45 – "You should come to a board meeting" 26:20 – Danielle discusses "agitators" disrupting meetings 26:42 – Why meetings were moved into an auditorium 27:07 – When protests escalated 27:46 – Public comment changes at special meetings 28:52 – How other Long Island districts handle comments 🏫 EDUCATION ISSUES 29:44 – Why Massapequa does not currently offer Universal Pre-K 30:33 – Danielle discusses choosing preschool during COVID 31:16 – What Danielle loves about Massapequa 31:40 – Why the community rallies together ⚽ SPORTS & TRANS ATHLETES 33:40 – Discussion about sports participation policies 34:07 – Danielle: "I think it's not safe" 34:43 – Supports for transgender students 35:37 – "We're focused on student strengths, not labels" 36:23 – "What you bring to the world matters" 🎤 FINAL THOUGHTS 36:45 – Tom almost pivots into campaign finance questions 37:03 – Danielle discusses campaign donations 37:17 – Final message to voters 38:16 – Celebrating students beyond college paths 38:33 – Danielle's closing statement 38:52 – Tom closes the show

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    39 mins
  • 469: Massapequa School Board Candidate: Bobby Bonett
    Apr 28 2026

    Tom Kelly runs into Bobby Bonett a magazine publisher running for school board in Massapequa, Long Island. - What follows is a raw, unscripted conversation about: Local politics The "Save the Chief" controversy Lawsuits vs taxpayer money Transgender policies in schools And why school boards shouldn't be this dramatic in the first place ⚠️ This is NOT an endorsement — it's a conversation. :00 – Podcasting from the back of a car 🚗 0:21 – Why this race matters (even if you're not local) 1:17 – George Santos & why local coverage matters 2:09 – "Left-leaning" in a right-leaning town? 3:03 – "A school board should be boring" 3:28 – The 2 biggest issues: Mascot + bathrooms 🪶 THE MASCOT CONTROVERSY 4:05 – History of the "Chief" debate 4:38 – "Save the Chiefs" — Bobby's stance 6:00 – 💰 Are taxpayer dollars funding lawsuits? 6:40 – How much is too much to spend? 8:43 – "We haven't won a single lawsuit" 💸 MONEY & CAMPAIGN QUESTIONS 9:27 – Rumors: Soros? Outside money? 10:03 – "Every dollar came from people in town" 10:44 – Spending $10,000 of his own money 11:44 – Should candidates run as a team? 🚻 TRANS POLICY & SCHOOL ISSUES 14:39 – Breaking down NY's transgender policy 15:08 – Teachers caught between state vs district rules 17:05 – Solution: privacy partitions in locker rooms 19:00 – Sports participation (case-by-case approach) 🏫 BIGGER PICTURE 20:42 – Can the public speak at meetings anymore? 21:28 – Are school boards becoming political platforms? 23:40 – "We're talking about courtrooms, not classrooms" 24:36 – "A school board should be boring" (again… for a reason) 🎤 FINAL THOUGHTS 25:51 – Agreeing to disagree 27:19 – Bobby's closing statement

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    28 mins
  • 467: Finding Mary Smith - Al Isaacs Finds Out He Is Adopted While Dealing With Parents' Dementia
    Apr 20 2026

    What would you do if you found out — in your 50s — that you were adopted?

    Tonight on The Tom Kelly Show, comedian and author Al Isaacs shares the unbelievable true story behind his book Finding Mary Smith. What starts as dealing with his parents' dementia turns into a life-altering discovery… and a search for the truth about who he really is.

    This episode has everything:

    • A shocking revelation from a doctor
    • A decades-long family secret
    • DNA tests, dead ends, and breakthroughs
    • A cross-country search for biological family
    • And a live, emotional surprise ending

    It's funny, raw, and deeply human — a story about identity, family, and what happens when your entire life suddenly makes more sense.

    Stick around to the end — the twist happens live.

    ⏱️ CHAPTERS (for apps that support them)

    00:00 – Opening & setting the stage
    00:20 – The premise: finding out you're adopted
    03:50 – The doctor call that changes everything
    05:00 – A Christmas story that defines Tom
    07:20 – Identity crisis & growing up "different"
    10:45 – Why Al never told his father
    12:40 – Dementia and realizing something's wrong
    14:25 – Beginning the search during COVID
    19:30 – DNA tests & ancestry surprises
    20:30 – "Gray market" adoption explained
    23:00 – First major breakthrough
    26:30 – Reaching out to a possible sister
    27:30 – "I've been looking for you for 20 years"
    30:50 – Discovering his real parents
    32:30 – Finding his mother online
    34:20 – The message that changes everything
    36:20 – Reaching out (and the fear of it)
    37:25 – Life after finding the truth
    39:30 – Why he wrote the book
    40:20 – Q&A and audience stories
    48:30 – Live surprise ending
    49:25 – Emotional reunion
    53:10 – Advice for others in similar situations

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    57 mins
  • 465 : Long Island Identity Crisis - Colbert End
    Mar 29 2026

    Tom talks about his continued identity crisis as Stephen Colbert ends his talk show and Long Island Real Estate agents start mimicking his Long Island content. Plus: some behind the scenes scoop on the end of the Late Show with Stephen Colbert and what goes into the show's production!

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    21 mins
  • Sunrise Mall Is Officially DEAD 😳 | Justin Timberlake DWI Drama + Apple Watch Tracking Your Sex?!
    Mar 9 2026

    Comedian Tom Kelly reacts to breaking Long Island news: the final store inside the Sunrise Mall in Massapequa is closing, officially ending an era for one of Long Island's most nostalgic malls. Tom dives into the memories, the controversy over turning the site into an Amazon distribution center, and why the death of malls says a lot about what's happening to communities across Long Island. Plus: Justin Timberlake's Long Island DWI arrest drama Why Timberlake is trying to block the police body cam footage And the weird discovery that the Apple Watch may track your sex life 🤯 Classic Tom Kelly ranting, storytelling, and Long Island nostalgia.

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    17 mins
  • 463: Long Island Favorites Things - Bars, Pizza, Malls, Clubs & Bad Decisions
    Mar 3 2026

    Podcasting from a loaner car on Sunrise Highway, blinded by golden hour like a true Long Island poet, comedian Tom Kelly and producer Steve Burger break down the ultimate list of Long Island's favorite things — past and present. From legendary bars and extinct malls… to pizza spots, chain restaurants, and 90s club stories that probably should've stayed in the 90s. If you grew up on Long Island, this episode is basically a time machine.

    Show Notes: Lex Burger's New Movie Strangers To Strangers

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    22 mins
  • 462: New York Electronic Chains Past And Present
    Feb 23 2026

    Electronics Stores: PC Richard, The Wiz, Circuit City, Best Buy, Crazy Eddie and . . . Tower Records (which did not belong on the list). Tom Kelly and comedian Steve Burger discuss electronic stores past and present. What went right? What went wrong? And how did we miss Radio Shack? - Plus: Tom Kelly will be swimming in a shark tank at the Long Island aquarium to promote People's ARC a non profit that helps children and adults with special needs. - Tickets For The Shark Tank Showdown https://www.peoplesarc.org/event/shark-tank-showdown-2/

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    24 mins