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Trump's Two-Week Deadline: A Pattern of Procrastination on Iran and Ukraine

6/20/2025
President Trump has once again set a two-week deadline to decide on military action against Iran, but critics highlight his history of missed deadlines. Will this time be different?
Trump's Two-Week Deadline: A Pattern of Procrastination on Iran and Ukraine
Trump's two-week ultimatum on Iran raises eyebrows as critics recall his history of procrastination on key issues. Is he truly a peace-maker or just buying time?

Donald Trump's Two-Week Deadline on Iran: A Familiar Pattern

President Donald Trump has recently announced a two-week deadline to determine whether the United States will launch an attack on Iran. However, CNN has highlighted that this is not the first time Trump has set such a timeline. A supercut aired last month showcased Trump’s frequent use of two-week pledges, emphasizing a concerning trend of letting these deadlines pass without any decisive action.

Repeated Promises and Diplomatic Delays

During a recent broadcast, host Kasie Hunt pointed out Trump’s troubling habit of allowing his deadlines to lapse. In the same segment, Karoline Leavitt was questioned about Trump's repetitive strategy, especially after his latest commitment to make a decision on Iran within the next two weeks. The pattern is evident; on May 19, for instance, Trump told a reporter he would prefer to address questions regarding the ongoing situation in Ukraine in “about two weeks.”

Hunt further analyzed the timestamps on various videos, revealing that just days later, on May 28, Trump again sidestepped inquiries about Russia and Ukraine, postponing his response for another two weeks. As these deadlines come and go, the lack of progress in securing a peace deal between Russia and Ukraine becomes even more pronounced.

Press Secretary's Defense of Trump's Tactics

On Thursday, reporters pressed Leavitt, Trump’s press secretary, about this recurring theme of two-week deadlines. One reporter asked, “He’s used this phrase about two weeks several times, in terms of ‘We expect a two-week deadline,’ and then you give another two-week deadline. How can we be sure that he’s gonna stick to this one, making a decision on Iran?”

In response, Leavitt initially attributed the ongoing international conflicts—specifically, those involving Russia-Ukraine and Israel-Iran—to the previous administration’s inadequacies. She argued that Trump’s reliance on a two-week timeline stems from his desire to seek diplomatic resolutions to complex global issues. “The last time the president said two weeks, you saw Russia and Ukraine have direct negotiations for the first time in years,” Leavitt stated. She emphasized Trump’s commitment to finding diplomatic solutions, highlighting his role as a “peace-maker-in-chief.”

Trump's Approach: Diplomacy and Strength

Leavitt continued to defend Trump’s approach, stating, “He is always interested in a diplomatic solution to the problems and global conflicts, and if there is a chance for diplomacy, the president will grab it.” She also added, “But he is not afraid to use strength.” This dual approach of seeking diplomacy while being prepared for military action underscores Trump's complex strategy in addressing international relations.

As the situation continues to unfold, the effectiveness of Trump’s two-week deadline strategy remains to be seen, particularly regarding the critical issue of U.S. actions towards Iran and the ongoing conflict in Ukraine.

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