The Mark Milton Show with The Smash

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Tax law meets St. Louis talk.

The gist

The Mark Milton Show with The Smash is a St. Louis-rooted talk show where legal and tax topics sit beside politics, sports, development, sponsor reads, and personal stories. Mark Milton brings the tax-law spine; The Smash brings the loose comic pressure.

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About The Mark Milton Show with The Smash

The Mark Milton Show with The Smash is a St. Louis-centered talk show built around law, taxes, politics, and local life. Its anchor is practical expertise. Mark Milton brings the perspective of a former Department of Justice Tax Division attorney, especially when the conversation turns to IRS disputes, conservation easements, estate taxes, gift-tax thresholds, and the mechanics behind legal incentives. Those sections are unusually concrete. The show explains how a tax concept works, why it matters, and where abuse or enforcement pressure can appear. Then the room veers sideways. The Smash adds a radio-banter energy that can turn a sponsor read, restaurant story, hospital recovery update, or stolen-truck account into its own segment. That contrast defines the show. One minute it is about syndicated conservation easements and appraisal fights; the next it is about furniture, Texas Roadhouse, or the etiquette of treating waitstaff well. Politics is a major lane, especially St. Louis County government, crime policy, regional cooperation, and local elections. Interviews with figures such as Mark Montevani give the show a civic forum quality, while guest co-host appearances bring in development, downtown projects, sports, and legal-career stories. It is not a quiet policy briefing. It is talk radio with a legal brain, a local map, and a taste for digression. The show works best for listeners who want tax and public-affairs conversation without losing the barbershop rhythm of jokes, interruptions, and familiar St. Louis references. Its rough edges are part of the format. The value is not polish; it is access to an informed local conversation that can move from IRS doctrine to neighborhood concerns without changing rooms.

Made for: Best for listeners who follow St. Louis politics, local business, public safety, tax issues, and personality-driven talk radio. It also fits anyone who wants legal and financial topics explained in conversational language.

What sets it apart: The show pairs real tax-law fluency with loose regional radio chemistry. Few business-and-politics podcasts move so easily from conservation easements to county races, downtown development, sponsor banter, and personal stories.

In their own words

Former U.S. Department of Justice (“DOJ”) Tax Division Trial Attorney Mark Milton and legendary radio personality and entertainer Asher Benrubi (“The Smash”) have teamed up to help the common man navigate an ever-increasingly complex legal, regulatory, and tax environment, while also discussing personal finance, current events, and politics. Guests include local and national business leaders, politicians, lawyers, professional athletes, and entertainers. Milton earned his accounting degree from the University of Illinois at Urbana-Champaign and law degree from St. Louis University. After law school, he was selected to participate in the DOJ’s Attorney General’s Honors Program in Washington,…

Why you'd press play

Mark Milton turns estate-tax thresholds into barstool talk, with Smash asking the question you were about to.

Press play if you want

  • tax rules translated through concrete examples instead of a lecture from the codebook
  • St. Louis politics and development talk with room for pointed opinions
Read the full recommendation in PlayNext →
tax-law explainersIRS problemsconservation easementsestate and gift taxesSt. Louis County politicscrime and public safetydowntown developmentlocal sports talk

Talks about

Podcasts like The Mark Milton Show with The Smash

Episodes

  1. 1

    Ep. 79, Seg. 3: Musk vs. Warren and 2021 Reflections

    ·12m
  2. 2

    Ep. 101: Emergency Podcast: STLTaxLawyer Falls Victim to Crime Wave

    ·38m
  3. 3

    Ep. 100, Seg. 1: St. Louis County Executive Candidate Mark Mantovani

    ·40m
  4. 4

    Ep. 100, Seg. 2: Cardinals, Illini, and Development Talk

    ·29m
  5. 5

    Ep. 99: Inflation, Geopolitical Potpourri, and Estate & Gift Taxes

    ·49m
  6. 6

    Ep. 98: Milty & The Smash Return from Summer Break

    ·48m
  7. 7

    Ep. 97: Bob Estes and Life on the PGA Champions Tour

    ·31m
  8. 8

    Ep. 96: Vacations, Radio Stories, and the Future of the Podcast

    ·1h 3m
  9. 9

    Ep. 61, Seg. 3: Small Business Tax Tips

    ·10m
  10. 10

    Ep. 61, Seg. 4: The GOATs

    ·8m
  11. 11

    Ep. 78, Seg. 1: Viva Las Vegas

    ·16m
  12. 12

    Ep. 72, Seg. 1: Mexico and Mandates

    ·22m
  13. 13

    Ep. 95: Hairstyles, the Opera, and Heartbreak in Texas

    ·46m
  14. 14

    Ep. 94: Rep. Dan Houx on Why Sports Gambling Legislation Failed in Missouri

    ·51m
  15. 15

    Ep. 93: Ryan Dickherber, St. Louis Attorney and U.S. Open Pickleball Champion

    ·39m
  16. 16

    Ep. 92: Social Media, Wally’s, and Things To Do In St. Louis

    ·53m
  17. 17

    Ep. 91: Jane Dueker, Democrat Candidate for St. Louis County Executive

    ·47m
  18. 18

    Ep. 90: Jay Randoph Jr. Previews The Masters

    ·29m
  19. 19

    Ep. 89, Seg. 1: The Slap Heard ’Round The World

    ·30m
  20. 20

    Ep. 89, Seg. 2: Biden’s Class Warfare Tax Proposal

    ·18m
  21. 21

    Ep. 88, Seg. 1: Supreme Court Nomination Hearings

    ·28m
  22. 22

    Ep. 88, Seg. 2: The Introduction of Drops, March Madness, and Milty’s RV

    ·18m
  23. 23

    Ep. 87: Treat Yourself and March Madness

    ·40m
  24. 24

    Ep. 86, Seg. 1: Former Billiken Troy Robertson

    ·25m
  25. 25

    Ep. 86, Seg. 2: Russia, Ukraine, and America’s Foreign Policy

    ·23m
  26. 26

    Ep. 85: ”Mr. Smith Goes To Prison” - Interview with Jeff Smith

    ·59m
  27. 27

    Ep. 84, Seg. 1: Winter Weather and Super Bowl Stories

    ·22m
  28. 28

    Ep. 84, Seg. 2: IRS Backlog and The Merits of Fighting

    ·24m
  29. 29

    Ep. 83: Milty Bought an RV

    ·37m
  30. 30

    Ep. 81, Seg. 1: Don Fort, Former Chief of the IRS Criminal Investigation Division

    ·39m
  31. 31

    Ep. 81, Seg. 2: School Mask Mandate Lawsuit

    ·13m
  32. 32

    Ep. 80, Seg. 1: The Show is a Free Agent

    ·16m
  33. 33

    Ep. 80, Seg. 2: Surprise Guest and St. Louis City Earnings Tax Lawsuit News

    ·14m
  34. 34

    Ep. 80, Seg. 3: Flying is a Disaster

    ·12m
  35. 35

    Ep. 79, Seg. 1: Missouri U.S. Senate Candidate Dave Schatz

    ·25m
  36. 36

    Ep. 79, Seg. 2: Tis The Season

    ·16m
  37. 37

    Ep. 102: Smash is Back!

    ·42m
  38. 38

    Ep. 78, Seg. 2: Nathan J. Hochman, former head of DOJ Tax Division

    ·21m
  39. 39

    Ep. 78, Seg. 3: Revenge of the Tax Nerds

    ·15m
  40. 40

    Ep. 77, Seg. 1: Thanksgiving, Guns ‘n Hoses, and MLB Lockout

    ·17m
  41. 41

    Ep. 77, Seg. 2: College Football Coaches Contracts

    ·13m
  42. 42

    Ep. 77, Seg. 3: Action Items for Taxes in December

    ·8m
  43. 43

    Ep. 77, Seg. 4: Asteroids and Kennedy vs. Fauci

    ·13m
  44. 44

    Ep. 76, Seg. 1: Canceling Conservatism

    ·16m
  45. 45

    Ep. 76, Seg. 2: Guns ‘n Hoses and Thanksgiving Meals

    ·15m
  46. 46

    Ep. 76, Seg. 3: Hockey, Fighting, and Doomsday Prepping

    ·21m
  47. 47

    Ep. 75, Seg. 1: Supply Chain, Vegas, and Aaron Rodgers

    ·15m
  48. 48

    Ep. 75, Seg. 2: The Fascinating Kyle Rittenhouse Trial

    ·16m
  49. 49

    Ep. 75, Seg. 3: Portnoy vs. Business Insider

    ·9m
  50. 50

    Ep. 75, Seg. 4: Year-End Tax Savings Tips

    ·10m
  51. 51

    Ep. 74, Seg. 1: An Apology To Warson Woods

    ·21m
  52. 52

    Ep. 74, Seg. 2: TV, Elections, and Biden‘s Nap

    ·19m
  53. 53

    Ep. 74, Seg. 3: More NFL Drama

    ·12m
  54. 54

    Ep. 73, Seg. 1: National Media Finally Covering Rams Lawsuit

    ·17m
  55. 55

    Ep. 72, Seg. 2: Year-End Tax Tips

    ·17m
  56. 56

    Ep. 73, Seg. 2: Councilman Tim Fitch

    ·20m
  57. 57

    Ep. 73, Seg. 3: Congressional Wrestling

    ·15m
  58. 58

    Ep. 72, Seg. 3: Fantasy Football and Weekly Picks

    ·12m
  59. 59

    Ep. 71, Seg. 1: Hola Mexico!

    ·15m
  60. 60

    Ep. 71, Seg. 2: Gruden, Rams Relocation, and NFL Hypocrisy

    ·22m
  61. 61

    Ep. 71, Seg. 3: Football Roundtable

    ·15m
  62. 62

    Ep. 70, Seg. 1: Return of The Smash

    ·12m
  63. 63

    Ep. 70, Seg. 2: Wild Card Recap

    ·11m
  64. 64

    Ep. 70, Seg. 3: Wrestling Legends and Urban Meyer

    ·14m
  65. 65

    Ep. 70, Seg. 4: The IRS Is Coming

    ·14m
  66. 66

    Ep. 69, Seg. 1: An Inside Look at Local Government

    ·20m
  67. 67

    Ep. 69, Seg. 2: Soccer and Bobblehead Talk

    ·19m
  68. 68

    Ep. 69, Seg. 3: Political Wrestling

    ·14m
  69. 69

    Ep. 68, Seg. 1: Beer Industry Trends

    ·17m
  70. 70

    Ep. 68, Seg. 2: Cardinals, LaRussa, and Baseball

    ·19m
  71. 71

    Ep. 68, Seg. 3: Sports Gambling Pick ‘Em

    ·15m
  72. 72

    Ep. 67, Seg. 1: Biden Tax Plan Proposes $2.5 Trillion in New Taxes

    ·13m
  73. 73

    Ep. 67, Seg. 2: General Milley‘s Actions During Trump‘s Final Days

    ·16m
  74. 74

    Ep. 67, Seg. 3: St. Louis City Earnings Tax Lawsuit Update

    ·13m
  75. 75

    Ep. 66, Seg. 1: Tom O‘Toole Discusses the Ascension Charity Classic

    ·17m
  76. 76

    Ep. 66, Seg. 2: Normandie Golf Course Renovation

    ·17m
  77. 77

    Ep. 66, Seg. 3: Golf Talk and Ryder Cup

    ·17m
  78. 78

    Ep. 65, Seg. 1: Yadi, Tattoos, and Cars

    ·12m
  79. 79

    Ep. 65, Seg. 2: Government Spending Insanity

    ·13m
  80. 80

    Ep. 65, Seg. 3: IRS Cracking Down on Crypto Users

    ·15m
  81. 81

    Ep. 65, Seg. 4: Concerts, Masks, and Panhandlers

    ·11m
  82. 82

    Ep. 64, Seg. 1: Chaos in Afghanistan

    ·19m
  83. 83

    Ep. 64, Seg. 2: Worker Shortage

    ·11m
  84. 84

    Ep. 64, Seg. 3: Civil Versus Criminal Tax Cases

    ·7m
  85. 85

    Ep. 64, Seg. 4: College Sports Landscape

    ·15m
  86. 86

    Ep. 63, Seg. 1: Mask Mandates in Schools

    ·18m
  87. 87

    Ep. 63, Seg. 2: The Fall of Afghanistan

    ·10m
  88. 88

    Ep. 63, Seg. 3: Potpourri

    ·22m
  89. 89

    Ep. 62, Seg. 1: Milton Family RV Trip Recap

    ·26m
  90. 90

    Ep. 62, Seg. 2: Holiday World

    ·16m
  91. 91

    Ep. 62, Seg. 3: More RV Life

    ·11m
  92. 92

    Ep. 61, Seg. 1: Radio Rules & The Olympics

    ·9m
  93. 93

    Ep. 61, Seg. 2: Lewis Reed, President of the St. Louis Board of Aldermen

    ·25m
  94. 94

    Ep. 60, Seg. 1: U.S. Senate Candidate Mark McCloskey

    ·26m
  95. 95

    Ep. 60, Seg. 2: The Incompetent Kim Gardner

    ·13m
  96. 96

    Ep. 60, Seg. 3: Potpourri

    ·12m
  97. 97

    Ep. 59, Seg. 1: America's Relationship with Food

    ·16m
  98. 98

    Ep. 59, Seg. 2: Interview with Billy Corgan of Smashing Pumpkins

    ·18m
  99. 99

    Ep. 59, Seg. 3: Concerts and Baseball Talk

    ·17m
  100. 100

    Ep. 82: Working in Trump’s White House with Attorney Darby Wade Grant

    Host Mark Milton and co-host The Smash discuss tax law, politics, and personal finance with a humorous anecdote about dinner etiquette.

    ·45m
  101. 101

    Ep. 102: Smash is Back!

    Hidden gem

    Mark Milton explains why YellowStone-related conservation easements can create huge tax deductions.

    Dec 9, 2022·42m·2 clips
  102. 102

    Ep. 101: Emergency Podcast: STLTaxLawyer Falls Victim to Crime Wave

    Hidden gem

    Mark Milton watched a burglar enter STL Tax Lawyer headquarters at 5:15 a.m. and immediately called police.

    Oct 27, 2022·38m·2 clips
  103. 103

    Ep. 100, Seg. 2: Cardinals, Illini, and Development Talk

    Dave Sweeney explains how the historic Armory could become St. Louis's next indoor entertainment venue.

    Oct 5, 2022·29m·2 clips
  104. 104

    Ep. 100, Seg. 1: St. Louis County Executive Candidate Mark Mantovani

    Hidden gem

    Mark Montevani says St. Louis County needs a crime plan with measurable goals, broad cooperation, and transparent reporting.

    Oct 5, 2022·40m·2 clips
  105. 105

    Ep. 99: Inflation, Geopolitical Potpourri, and Estate & Gift Taxes

    Mark Milton explains how $17,000 annual gifts can reduce a potential $12 million estate-tax exposure.

    Sep 28, 2022·49m·2 clips
  106. 106

    Ep. 98: Milty & The Smash Return from Summer Break

    Sep 21, 2022·48m
  107. 107

    Ep. 97: Bob Estes and Life on the PGA Champions Tour

    Sep 13, 2022·31m
  108. 108

    Ep. 96: Vacations, Radio Stories, and the Future of the Podcast

    Jun 8, 2022·1h 3m
  109. 109

    Ep. 95: Hairstyles, the Opera, and Heartbreak in Texas

    May 26, 2022·46m
  110. 110

    Ep. 94: Rep. Dan Houx on Why Sports Gambling Legislation Failed in Missouri

    May 18, 2022·51m
  111. 111

    Ep. 93: Ryan Dickherber, St. Louis Attorney and U.S. Open Pickleball Champion

    May 4, 2022·39m
  112. 112

    Ep. 92: Social Media, Wally’s, and Things To Do In St. Louis

    Apr 29, 2022·53m
  113. 113

    Ep. 91: Jane Dueker, Democrat Candidate for St. Louis County Executive

    Apr 20, 2022·47m
  114. 114

    Ep. 90: Jay Randoph Jr. Previews The Masters

    Mark Milton hosts a show discussing tax, legal, and financial topics, opening with a lighthearted golf anecdote with guest Jay Randolph Jr.

    Apr 6, 2022·29m
  115. 115

    Ep. 89, Seg. 1: The Slap Heard ’Round The World

    Mar 30, 2022·30m
  116. 116

    Ep. 89, Seg. 2: Biden’s Class Warfare Tax Proposal

    Mar 30, 2022·18m
  117. 117

    Ep. 88, Seg. 1: Supreme Court Nomination Hearings

    Mar 23, 2022·28m
  118. 118

    Ep. 88, Seg. 2: The Introduction of Drops, March Madness, and Milty’s RV

    Mar 23, 2022·18m
  119. 119

    Ep. 87: Treat Yourself and March Madness

    Mar 16, 2022·40m
  120. 120

    Ep. 86, Seg. 2: Russia, Ukraine, and America’s Foreign Policy

    Mar 10, 2022·23m
  121. 121

    Ep. 86, Seg. 1: Former Billiken Troy Robertson

    Mar 10, 2022·25m
  122. 122

    Ep. 85: ”Mr. Smith Goes To Prison” - Interview with Jeff Smith

    The episode opens with a furniture ad and banter before introducing guest Jeff Smith, author of a book, for an interview likely covering legal and political topics.

    Feb 28, 2022·59m
  123. 123

    Ep. 84, Seg. 2: IRS Backlog and The Merits of Fighting

    Feb 21, 2022·24m
  124. 124

    Ep. 84, Seg. 1: Winter Weather and Super Bowl Stories

    Feb 21, 2022·22m
  125. 125

    Ep. 83: Milty Bought an RV

    Feb 11, 2022·37m
  126. 126

    Ep. 82: Working in Trump’s White House with Attorney Darby Wade Grant

    Mark Milton and co-hosts discuss tax law, politics, and personal finance with a humorous, conversational tone.

    Jan 28, 2022·45m
  127. 127

    Ep. 81, Seg. 1: Don Fort, Former Chief of the IRS Criminal Investigation Division

    Jan 21, 2022·39m
  128. 128

    Ep. 81, Seg. 2: School Mask Mandate Lawsuit

    Jan 21, 2022·13m
  129. 129

    Ep. 80, Seg. 3: Flying is a Disaster

    Jan 12, 2022·12m
  130. 130

    Ep. 80, Seg. 2: Surprise Guest and St. Louis City Earnings Tax Lawsuit News

    Jan 12, 2022·14m
  131. 131

    Ep. 80, Seg. 1: The Show is a Free Agent

    Jan 12, 2022·16m
  132. 132

    Ep. 79, Seg. 3: Musk vs. Warren and 2021 Reflections

    Dec 17, 2021·12m
  133. 133

    Ep. 79, Seg. 1: Missouri U.S. Senate Candidate Dave Schatz

    Dec 17, 2021·25m
  134. 134

    Ep. 79, Seg. 2: Tis The Season

    Dec 17, 2021·16m
  135. 135

    Ep. 78, Seg. 1: Viva Las Vegas

    Dec 10, 2021·16m
  136. 136

    Ep. 78, Seg. 2: Nathan J. Hochman, former head of DOJ Tax Division

    Dec 10, 2021·21m
  137. 137

    Ep. 78, Seg. 3: Revenge of the Tax Nerds

    Dec 10, 2021·15m
  138. 138

    Ep. 77, Seg. 4: Asteroids and Kennedy vs. Fauci

    Dec 3, 2021·13m
  139. 139

    Ep. 77, Seg. 1: Thanksgiving, Guns ‘n Hoses, and MLB Lockout

    Dec 3, 2021·17m
  140. 140

    Ep. 77, Seg. 3: Action Items for Taxes in December

    Dec 3, 2021·8m
  141. 141

    Ep. 77, Seg. 2: College Football Coaches Contracts

    Dec 3, 2021·13m
  142. 142

    Ep. 76, Seg. 1: Canceling Conservatism

    Nov 19, 2021·16m
  143. 143

    Ep. 76, Seg. 2: Guns ‘n Hoses and Thanksgiving Meals

    Nov 19, 2021·15m
  144. 144

    Ep. 76, Seg. 3: Hockey, Fighting, and Doomsday Prepping

    Nov 19, 2021·21m
  145. 145

    Ep. 75, Seg. 4: Year-End Tax Savings Tips

    Nov 12, 2021·10m
  146. 146

    Ep. 75, Seg. 3: Portnoy vs. Business Insider

    Nov 12, 2021·9m
  147. 147

    Ep. 75, Seg. 2: The Fascinating Kyle Rittenhouse Trial

    Nov 12, 2021·16m
  148. 148

    Ep. 75, Seg. 1: Supply Chain, Vegas, and Aaron Rodgers

    Nov 12, 2021·15m
  149. 149

    Ep. 74, Seg. 1: An Apology To Warson Woods

    Nov 5, 2021·21m
  150. 150

    Ep. 74, Seg. 2: TV, Elections, and Biden‘s Nap

    Nov 5, 2021·19m