The conservative New York Times columnist faulted the president for failing to ask important questions -- such as how many casualties could be expected -- before ordering a military attack that he abruptly called off after launching warplanes.
"Reagan would have had a good plan, had an idea of how to execute it, would have executed it rapidly and it would have been over," Stephens told MSNBC's Stephanie Ruhle. "He did that over the Gulf of Sidra in Libya in 1981, he did that again in 1988 when there was a one-day naval battle in which we sank about half of the Iranian operational fleet."
"What Trump has done," Stephens added, "was demonstrate to the Iranians he is a Twitter tiger. This is a guy who likes to speak loudly, is full of bluster, but the fact is he is not only a very cautious president, but he's an extraordinarily disorganized president."
He said reports about Thursday's aborted strike, and Trump's tweets about the decision Friday morning, showed an alarming breakdown inside the administration.
"You just have to ask yourself the kind of extraordinary breakdown in normal American governance that a president orders a strike, but only asks the follow-on question, is it proportionate?" Stephens said. "How many people on the other side are going to die, when the planes are already in the air?"
Stephens said Trump displayed characteristics that Republicans had always tried to assign to recent Democratic presidents.
"The accusation the Republicans always made about President Clinton, President Obama, is they were weak, hesitant, pulled out at the last minute, signaled weakness to our enemies, and Trump is actually fulfilling exactly that kind of stereotype as a Republican," he said.
