Back in February 2026, before the war started, Joint Chiefs Chairman Gen. Dan Caine was advising Trump and top officials that a military campaign against Iran could carry significant risks, particularly the possibility of becoming entangled in a prolonged conflict. Axios
Sources described Caine as a "reluctant warrior" on Iran, noting he saw the stakes as higher than other operations, with greater risk for entanglement and American casualties. Axios
Trump pushed back on those reports publicly. He posted on Truth Social that Caine would like to avoid war, but believes it would be "something easily won" if necessary, and emphasized that he himself would make the final call. ABC News
However, the war went ahead anyway. The U.S. and Israel launched a surprise attack on Iran in early March 2026 — dubbed "Operation Epic Fury" — which killed Supreme Leader Khamenei and other Iranian officials. Wikipedia Iran retaliated with drone and missile strikes on U.S. military bases and Israeli targets.
Now, a month into the conflict, the war is growing increasingly unpopular domestically, with gas prices surging past $4 a gallon, stock markets tumbling, and 13 American service members confirmed killed. Time Caine's pre-war caution is looking pretty prescient in hindsight.
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