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Trump’s Iran headaches are mounting

(CNN) — The Iran war hasn’t gone well for President Donald Trump since, well, shortly after it began.

Despite extensive US military attacks and economic pressure, Iran hasn’t felt the need to capitulate to Trump’s demands. And even when there have been ceasefires with favorable terms for Iran, Tehran still didn’t abide by them.

But Trump’s headaches with the war are mounting. And many of them extend beyond the battlefield and the negotiating table.

Some of the recent developments:

  • Trump’s newly reported secret plane switch in Turkey due to a potential Iranian threat is raising major questions about the administration using staff and media as decoys. The revelation is also undercutting the administration’s claims about Iran’s diminished capabilities and leading to mockery of Trump, including by Iranian state media.
  • The United States’ munitions shortfall problem — which Trump was warned about before the war began — appears to be coming to a head.
  • There are increasing signs of Trump administration officials and allies growing weary of the war and looking for or urging an off-ramp.
  • There are now also increasing reports of declining living conditions and mental health aboard the USS Abraham Lincoln amid an extraordinarily long deployment to support the war effort. CNN reported Thursday that one sailor went overboard wearing a life vest, with a US official saying the Navy viewed the event as a “mental health” incident.

And through it all, Iran only appears to be growing bolder and upping its demands — perhaps believing that its leverage is increasing.

All of the above threatens Trump’s ability to keep prosecuting the war. And these developments add to the costs of a war — now in its sixth month — whose purpose Americans have never been convinced of in the first place. The president insists he’s not feeling the time pressure, but some in his party would beg to differ with the midterms looming.

The plane switch in particular threatens to add a layer of scandal over the already unpopular war. And as much as anything, it undercuts the administration’s claims to have decimated Iran militarily.

This week we learned that the Trump administration feared a threat from Iran was serious enough that it warranted sneaking the president off Air Force One for his departure from Turkey last month. (CNN reported Wednesday that the threat involved a shoulder-fired missile.)

The munitions supply has long been a sleeping giant. CNN has reported that Joint Chiefs of Staff Chairman Gen. Dan Caine and other military leaders warned Trump before the war began that the stockpiles could be an issue in a protracted conflict.

Trump seemed to anticipate a much shorter war, lasting four to six weeks or so. But that’s not what he’s gotten. And increasing reports, including from CNN, suggest Caine’s warnings were well-founded and that key munitions are significantly depleted. The US military has exhausted nearly 80% of its interceptors for a key missile defense system, known as THAAD.

The Trump administration has claimed it has plenty of munitions to finish the job in Iran. But that doesn’t address whether the war might cause the US to be so short of critical munitions — which take time to replenish — that it leaves the country exposed or might embolden an adversary like China to try and invade Taiwan.

That’s increasingly a cost-benefit analysis that administration officials will need to consider. But it’s already a dynamic that threatens Trump’s ability to apply pressure on Iran.

A major question, of course, is whether military or administration officials could even prevail upon Trump if they regard the munitions issue as being dire. But there are increasing signs that key figures are growing weary of the war and sending signals that it might be time to ramp it up.

CNN reported last week that Caine has privately made clear to other top Trump advisers that the administration needs to find an off-ramp from the war because the military options on the table to escalate the conflict could backfire, and airpower alone is unlikely to achieve Trump’s objectives.

There are also signs that loyal Trump allies are increasingly concerned about the war costing Republicans in the 2026 midterm elections. House Speaker Mike Johnson said recently that “we’ve got to wrap it up,” and Fox News host Laura Ingraham has said the “clock is ticking.” (Indeed, the Guardian recently reported that more Iran war skepticism is seeping in on the normally rah-rah airwaves of Fox.) Even cheerleaders for Trump and his war effort like right-wing influencer Benny Johnson have signaled it’s time to move on.

“Foreign wars with no end in sight are always unpopular. They will always be political cancer,” Johnson posted on X two weeks ago. He added: “End the war. Be done. Refocus on America. Gas, grocery, home prices and immigration. Thats how we win.”

The length of the war also appears to be contributing to another problem for the administration’s ability to keep prosecuting it: fatigue, poor living conditions and declining mental health among the service members tasked with supporting the war effort.

News outlets Stars and Stripes and the Navy Times have reported multiple attempts by crew members aboard the USS Abraham Lincoln to jump overboard. A sailor recently went overboard, CNN reported, before being rescued.

And around 200 family members of Lincoln crew members voiced concerns about the situation — including lack of supplies, food shortages and water contamination — at town halls last week in San Diego. The Lincoln has been deployed since November and hasn’t made a port call in more than 200 days, which Democratic Sen. Richard Blumenthal of Connecticut said is a modern-day record for consecutive days at sea.

The US Navy said it takes “every service member’s well-being seriously and have religious, medical and mental health professionals available to assess and address concerns as they arise.”

But the emerging story epitomizes Trump’s problems.

He seems to regard continuing the war and keeping up the economic pressure on Iran as largely a cost-free endeavor. The US doesn’t have boots on the ground and there aren’t constant stories about troop deaths. Rising gas prices have been the war’s biggest political problem.

But as the situation stretches months beyond when the administration signaled it would end, other problems are seeping in. Some of them make continuing the war more difficult on a practical level, while others suggest the stalemate will keep giving the administration political problems that it — and its allies — have to reckon with.

And given the war was already looking like an albatross and a quagmire – with the midterms less than three months away — these are pretty inauspicious developments.

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IRS proposal would force nonprofits to disclose leaders’ terrorism convictions

Washington — The Trump administration is weighing a proposal to require nonprofits to disclose in their annual tax filings whether their top officials have been convicted of certain financial or terrorism-related crimes, sources with direct knowledge of the matter told CBS News.The IRS disclosure requirement would be added to the Form 990, the annual return that nonprofit groups file with the agency, said the sources, who spoke on the condition of anonymity because they were not authorized to talk publicly. Federal officials have viewed it as an effort to pressure tax-exempt groups to cut ties with people who have such criminal records and ensure that donors can make informed decisions about how to best direct their money, the sources said.Convictions that would have to be reported include providing material support to terrorists, fraud, money laundering, securities fraud, tax evasion, theft and civil judgments from Securities and Exchange Commission or state securities regulators' enforcement actions.The IRS proposal would not force groups to identify which officer, director or trustee was convicted, according to the sources. It is not a violation of federal law for people with felony convictions to serve on a nonprofit board.The proposal is expected to relate to convictions that occurred within the last 10 years. Nothing has been finalized, and it is one of at least two proposed revisions to the Form 990 moving through the Treasury Department and the IRS. Another proposal announced in April would impose new disclosure requirements for nonprofits that receive government funding. "No one has a right to privacy of their criminal record," said Tom Jones, an ally of President Trump who leads the conservative American Accountability Foundation nonprofit. "If your board members are convicted criminals, I am hard pressed to understand why you have a problem with that being publicized. You should have to explain why those people are on your board."A spokesperson for the Treasury Department said that it is considering "a range of measures to strengthen accountability for nonprofit organizations" and that the agency "will continue to follow the money to ensure tax-exempt status is not exploited to facilitate illicit activity."Inside the IRS, some officials have privately raised concerns about the conviction-related proposal and what the agency could lawfully do with the information — as well as questioned how it relates to enforcement of tax laws, multiple sources familiar with the conversations told CBS News. These IRS officials have said they view the effort as a form of potential political targeting that could draw legal challenges, including on free speech grounds, sources said."This disclosure rule goes directly to guilt by association," said Roger Colinvaux, a law professor at the Catholic University of America and former counsel to the nonpartisan Joint Committee on Taxation in Congress. "There's no federal law that says a nonprofit cannot have a convicted felon on their board. It could just create a stigma and chill association. This would reach deeply into American civil society."One of the sources with direct knowledge of the proposal, who spoke on the condition of anonymity because they were not authorized to talk publicly, suggested that such a move is not much different from material disclosures that publicly traded companies are required to make to help the investing public make informed decisions. The source also suggested that the proposal could help the IRS move faster to suspend or revoke the tax-exempt status of nonprofits if they fail to disclose convictions of any of their leaders. That's because the nonprofit officials who submit the Form 990 must attest to its accuracy under the penalty of perjury, and fact-checking whether board members have undisclosed criminal convictions would be a relatively simple task for the IRS to do, the source added.The disclosure efforts come amid a broader effort by the Trump administration to target left-leaning nonprofits. Mr. Trump signed a national security memorandum last year that directed the IRS to refer groups believed to be financing "domestic terrorism" to the Justice Department. In March, CBS News was first to report that the FBI and IRS Criminal Investigation teamed up to launch a "command post" tasked with investigating possible links between nonprofits and terrorism.That followed a directive from then-Attorney General Pam Bondi late last year for law enforcement agencies and federal prosecutors to probe the anti-fascist antifa movement and other "extremist groups." The memo asked law enforcement agents to consider investigating extremist groups for potential fraud and tax crimes. Antifa, a decentralized coalition of far-left activists, is not a formal organization and has no board members or officers.A number of federal criminal investigations and prosecutions targeting nonprofits are now underway. The highest-profile prosecution focuses on the Southern Poverty Law Center, which is accused of misleading donors and banks by funneling money to informants for white supremacist groups. The SPLC has pleaded not guilty.In another matter, Neville Roy Singham, the wealthy husband of the founder of the progressive nonprofit Code Pink and benefactor of far-left political causes, is under criminal investigation in Manhattan, CBS News previously reported. That investigation began by looking into possible violations of the Foreign Agents Registration Act and has since expanded into a criminal tax probe over whether money was unlawfully funneled through nonprofits he controls and whether he lied on tax forms for those nonprofits.Earlier this year, eight people affiliated with a North Texas antifa group were sent to prison for sentences ranging from 30 to 100 years, after they were convicted for providing material support to terrorists and other offenses, including the attempted murder of an Alvarado police officer at the Prairieland Detention Center.The proposal comes as the Trump administration has also focused its attention on fraud in recent months and spotlighted the pandemic-era Feeding Our Future scandal in Minnesota as an example of abuses in the nonprofit sector. So far, the estimated $250 million scheme has resulted in 68 convictions or guilty pleas. Some states already ask tax-exempt groups a version of the question the IRS is now weighing. California requires charities soliciting donations in the state to disclose whether their officers or directors have been convicted of certain offenses, as part of an effort to prevent charitable fraud. Under state law, a court can remove a director for fraud, dishonest acts or breach of duty in a case the attorney general can bring. But federal law has no equivalent remedy, said Ellen Aprill, a senior scholar in residence at UCLA Law School's center for philanthropy and nonprofits — meaning the IRS would be collecting information it has no stated authority to act on. "I think there is the potential for a fishing expedition," Aprill said.Alexander Reid, a partner at the law firm BakerHostetler who specializes in tax-exempt organizations, said the proposal about board members would collide with the Supreme Court's 2021 decision in the case Americans for Prosperity Foundation v. Bonta. The ruling struck down a California requirement that charities turn over lists of their major donors."The bulk collection and disclosure of sensitive information from tens of thousands of charities, much of which would never be relevant to tax administration or charitable-law enforcement, would fail exacting scrutiny by chilling freedom of association without furthering a narrowly defined governmental interest," Reid said.The IRS has come under the spotlight more recently over questions about political interference. Ken Kies, who was the top tax official at the Treasury Department, was ousted in July after warning that the White House was at risk of illegally involving itself in IRS audits, The Wall Street Journal reported.Steven Toscher, a tax attorney in California, said that from a good governance perspective, he does not see a problem with requiring nonprofits to disclose terrorism-related convictions of their board members. At the same time, he said, it's fair to raise questions about why the Trump administration wants this information, what it might use it for and how it defines terrorism."It's hard to view this in isolation of just good corporate nonprofit governance because of the executive who is proposing it," he said. "They have an agenda, so it's hard to filter this." Diane Yentel, president and CEO of the National Council of Nonprofits, which represents roughly 25,000 organizations, sees the administration's proposal for officers as part of a pattern of Republicans seeking to target groups in the sector that are not aligned with Mr. Trump."Nonprofits welcome reasonable regulation as a way to maintain public trust," said Yentel, but the proposal is "a step too far when viewed in the context of all of the administration's actions and rhetoric of the last 18 months, including equating some nonprofits to 'domestic terrorists' or 'enemies' of the American people."She said complying with the disclosure "would take precious time and resources away from nonprofits' core work of serving communities."
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