Tom Kelly Show | LaughTrack

471: Massapequa Board Candidate Cheryl LepreMay 11, 2026 · 39 minComedian 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"