Conservative insider highlights Trump’s greatest 'vulnerability'

02 September

Bill Kristol speaking at the Art Museum at Arizona State University in Tempe, Arizona on March 3, 2017 (Gage Skidmore/Flickr)

Although Republicans held the U.S. Senate in the 2018 midterms, they suffered a major setback that year when Democrats flipped the U.S. House of Representatives and enjoyed a net gain of 40 House seats. The issue that fueled that blue wave more than any other was health care. Democrats hammered President Donald Trump and then-House Speaker Paul Ryan (R-Wisconsin) relentlessly for their efforts to repeal the Affordable Care Act of 2010, a.k.a. Obamacare — and their messaging worked.

Seven years later, in 2025, Never Trump conservative Bill Kristol argues that health care is still a major liability for Trump and GOP lawmakers.

In an article published by The Bulwark on September 2, Kristol notes that Trump appeared "concerned" about voters' views on health care when he addressed the subject in a Labor Day post on his Truth Social platform.

"I don't know if Donald Trump has a personal health problem," the conservative journalist writes, "but I'm confident he has a political health care problem…. The Centers for Disease Control is 'being ripped apart,' he fretted. Surely, Donald Trump hasn't suddenly developed an appreciation for the importance of not 'ripping apart' government agencies. But he is, I’d judge, alarmed about the political effects of what's happening there."

Kristol continues, "And who's been doing that ripping apart? His own secretary of health and human services, Robert F. Kennedy Jr. Trump's deputy chief of staff, Stephen Miller, said on Friday, (August 29) that Kennedy is 'a crown jewel' of Trump's administration. Trump’s post yesterday did not repeat this encomium."

From chaos at the Centers for Diseases Control and Prevention (CDC) to cuts to Obamacare and Medicaid, Kristol considers health care a major "vulnerability" for Republicans in the 2026 midterms.

"After all, Trump has always insisted he wouldn’t cut Medicaid and still insists he hasn't, even as the reconciliation bill that he championed and signed did so," Kristol explains. "Democrats are going to make reversing those cuts a centerpiece of their September messaging. They're going to hammer Republicans for every rural hospital closure that happens between now and November 2026. Trump knows that's a vulnerability. And that's not the only vulnerability."

Kristol continues, "Last week, Ryan Fournier, head of Students for Trump, interrupted his normal Trump cheerleading and transgender bashing to warn about the political consequences of allowing federal support to end for the insurance premiums on the state exchanges set up in the Affordable Care Act…. As of now, Republicans haven't acted and don’t intend to act to extend those tax credits. They expire at the end of this year. Insurers are already preparing to raise premiums."

Kristol predicts that Democrats, in the months ahead, will ramp up their attacks on Trump's health care policies.

"So, as we head into the September showdown on next year's budget, Republicans have handed Democrats a politically powerful agenda on the issue of health care: Undo the Medicaid cuts," the Never Trumper observes. "Keep the health insurance tax credits. Provide vaccines. Trump is now on the unpopular side of these arguments. He doesn't care about the substance, and will be tempted to give in and take these attacks off the table. But that would fracture his base."

Kristol adds, "MAHA doesn’t like vaccines. Many congressional Republicans, not just the Freedom Caucus, hate concessions on Medicaid or Obamacare. So Trump's path ahead is rocky. The Democrats’ path, on the other hand, is pretty simple: Promote and publicize doctors, nurses, hospital administrators, and patients and their families, explaining the damage Trump is doing. And then spend all month in D.C. fighting on their behalf. In 1994, 2010, and 2018, the midterms focused on health care. And they were very bad for the party in power. This September is key to a repeat performance in 2026."

Bill Kristol's full article for The Bulwark is available at this link.

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