Aug 27, 2026 · 1h 21m
ICE arrests and Trump’s midterm machine face scrutiny
Sam Stein Used to Be a Thief
The episode connects expanding immigration enforcement, Republican electoral planning, and Florida corruption allegations to the broader risks of Trump-era governance.
- 1The hosts examine ICE arrests of noncriminal immigrants and deportations to countries with poor human-rights records.
- 2Trump’s super PAC strategy relies on a large war chest, donor pressure, and a Republican effort to manage midterm losses.
- 3Allegations involving Ron DeSantis and Hope Florida expose the tangled political stakes surrounding Medicaid settlement money.
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Sam Stein confesses to stealing a newspaper as a young journalist, prompting an extended exchange about guilt, shame, and the episode’s title.
The brief
Tim Miller and Sam Stein open with ICE arrests of noncriminal immigrants, deportations to countries with poor human-rights records, and the administration’s expansive enforcement resources.
They then examine Trump’s super PAC war chest, pressure on corporations and wealthy donors, and the Republican strategy for surviving the midterms, including Iowa’s uncertain terrain.
The discussion turns to allegations that Ron DeSantis’s administration diverted Medicaid settlement money into the Hope Florida Foundation, a convoluted scandal with implications for Florida politics.
A recurring cabinet ranking weighs officials including Markwayne Mullin, Pam Bondi, Sean Duffy, RFK Jr., Pete Hegseth, and Marco Rubio by incompetence and damage.
The mailbag shifts from media personalities and failed campaigns to alternate careers, baseball, mortgages, and dogs before Sam Stein confesses to stealing a newspaper as a young journalist.
The confession becomes the episode’s comic center: a discussion of guilt and shame that gives the sprawling mailbag a sharper, more personal ending.
Featuring
Markwayne Mullin
Ron DeSantis
Donald John Trump
The New York TimesListen to the full episode and explore every guest, topic, and moment on PodLume.