Trump’s $400 Million Midterm Strategy Could Backfire Spectacularly (w/ Sam Stein) | Bulwark Daily

We’ve hit the August doldrums, so Tim is taking the daily pod on a little excursion. The Bulwark community delivered some epic mailbag questions, one of which prompted Sam to make one of the nerdiest confessions ever. Also, Tim and Sam adjust their Cabinet member rankings: Marco is an utter catastrophe, RFK Jr. is failing on all fronts, and Kelly Loeffler is proof that aliens exist. Plus, DeSantis is doing some seemingly dirty dealing down in Florida, ICE arrests are soaring—and here’s hoping that Trump’s super PAC spends millions on ads for the midterms extolling what a great job he’s doing as president. Sam Stein joins Tim Miller.

Show notes:

NYT on the surge in ICE arrests:
https://www.nytimes.com/interactive/2026/08/27/us/ice-immigrant-arrests-trump-deportation-dhs.html

Vanity Fair piece on Lutnick that Tim referenced:
https://www.vanityfair.com/story/pierre-hotel-howard-lutnick-deal?

The Atlantic on Trump's midterms ad campaign:
https://www.theatlantic.com/politics/2026/08/trump-midterms-ads-maga/688409/?gift=AO0MhSsTDaHgiP_RxFGfB390J_Y81TidH85bf5rTIdM&utm_source=copy-link&utm_medium=social&utm_campaign=share

Tim's latest 'Take' on Trump's immigration policy
https://www.thebulwark.com/p/trumps-immigration-policy-is-sending?

Sam's 'Take' from May on the DeSantis Medicaid scandal
https://www.thebulwark.com/p/the-10m-scandal-that-could-bring?

Alien Kelly Loeffler video
https://x.com/PeterHamby/status/2088289692286599626?s=20

Bulwark LIVE: GOOD FIGHT TOUR with Tim, Sarah, Sam and JVL is coming to the Southeast in October. Tickets are on sale NOW. Head to https://TheBulwark.com/Events for details and to get your tickets.

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00:00:00 Welcome
00:02:58 ICE Expands Noncriminal Arrests
00:11:19 Trump’s Midterm Ad Strategy
00:21:07 Florida Medicaid Money Scheme
00:27:35 Worst Cabinet Rankings Return
00:31:30 Sam’s Worst Five
00:37:42 Tim’s Worst Five
00:43:56 Mailbag: Morning Routines
00:52:06 Campaign Losses Revisited
00:55:41 Sam’s Newspaper Theft Confession
00:57:45 Alternate Jobs for Officials
01:06:57 Why Sam Chose a Labradoodle