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Why Gen. Stanley McChrystal almost got kicked out of West Point

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Why Gen. Stanley McChrystal almost got kicked out of West Point

During his illustrious career in the U.S. Army, Stanley McChrystal became a four-star general. McChrystal was commander of Joint Special Operations Command when U.S. forces captured Saddam Hussein in Iraq in 2003. McChrystal was also JSOC’s chief when it targeted and killed al-Qaida’s Abu Musab al-Zarqawi three years later.

Even if his time in uniform did not end like he might have hoped—he submitted his resignation to President Barack Obama in 2010 after a controversial Rolling Stone article—McChrystal did his family proud. He continued a legacy that his father and grandfather, both of whom were Army officers, established. McChrystal idolized his father, Herbert, and wanted nothing more than to be like him, he told interviewer Chris Williamson on the “Modern Wisdom” podcast last year.

Despite his pedigree, McChrystal’s rise in the military was not linear. There were some bumps along his path, sometimes because of his own doing. That was especially true during his time in the U.S. Military Academy at West Point, New York.

McChrystal, 72, admitted on the podcast that he struggled academically as a cadet. His biggest issues, however, weren’t in the classroom. McChrystal got into trouble because he lacked the maturity and wisdom to consider properly the consequences of bad decisions.

In time, McChrystal became a disciplined and efficient leader. While he was at the academy in the 1970s, he had to learn some universal truths.

A Shaky Start

McChrystal’s initial issues at West Point began when he disrespected a superior cadet. A few months later, McChrystal told Williamson, he made life more difficult for himself again after he was caught drunk.

As the future general explained it, that infraction earned him a series of punishments. McChrystal received demerits and special confinement in your room. McChrystal said it was akin to being in prison. The only time that he went outside those four walls was when, holding his rifle, he walked back and forth in a courtyard for hours.

That punishment for drinking lasted three months, McChrystal recalled. It ended on a Friday during football season, and to celebrate, McChrystal, another cadet, and their dates attended the Army football game that weekend.

After the game, they planned to attend a dance that night. While the young women left to prepare for the evening, McChrystal and the other cadet went to their room to relax.

They started drinking.

“The last thing I remember is getting caught again,” McChrystal confessed on “Modern Wisdom.”

“I Put it All at Risk”

McChrystal thought that was it. He was certain that a second infraction for drinking would get him booted from the academy. After McChrystal was sober, he appeared before the Commandant’s Board—which meted out discipline at West Point.

McChrystal told Modern Wisdom that the board’s president was a colonel who served in the Vietnam War. When McChrystal appeared before him, the combat veteran admitted his confusion.

“I just don’t get it,” the colonel said to a clearly nervous McChrystal. “You just got off this other one, and now we’re about to hit you with another big slug [punishment].”

McChrystal couldn’t have been more relieved after the Commandant Board’s head said that, because that implied he wasn’t getting kicked out of the academy altogether. And McChrystal was right. Although the punishment included two more months of confinement and 44 hours of walking in the courtyard, he was still a cadet.

Looking back, McChrystal understands how lucky he was.

“I put it all at risk,” McChrystal said to “Modern Wisdom’s” Williamson. “It’s a great story when I’ve gone up and spoken at West Point a few times. Here I am, a retired four-star general. I can joke about how many punishments I had and how close I was to getting thrown out. But if I’d gotten thrown out, it wouldn’t be a funny story. It would be something I probably didn’t mention. It would be an opportunity lost.”

At least McChrystal avoided the worst-case scenario. He didn’t have to tell his family—including his father, who was then on active duty—that his terrible decision-making led to his ouster from West Point.

Instead, he got a second chance. McChrystal began to mature a bit, and he had the good fortune of meeting his future wife, Annie. He also got a new tactical officer, he told “Modern Wisdom,” to begin his junior year. In their first meeting, the officer predicted that McChrystal had the makings of an excellent officer.

Given McChrystal’s spotty record, that revelation surprised him.

“I wanted to lean over and see whether he was looking at the right file,” McChrystal joked. “I said, ‘You know who you’re talking to?’ And he said, ‘The stuff that you’re not good at is here at West Point. It doesn’t matter.’”

Those words gave McChrystal a much-needed boost of confidence. As that officer correctly foresaw, the key for McChrystal was to survive his final two years as a cadet, stay out of trouble, and graduate. McChrystal did all three and said his commissioning as a second lieutenant in 1976 got him to where he always saw himself.

To the stuff that McChrystal actually was good at. Being a good soldier and team player. Displaying effective leadership. Making sound decisions in extremely stressful circumstances.

The Lesson from a Close Call

A half-century later, McChrystal doesn’t look back at his West Point years with any hint of nostalgia. They were necessary to his education, and he was proud he persevered. In the process, McChrystal became a more disciplined cadet (and later service member).

He desperately wanted to follow his father’s example and become a soldier. Realizing how close he came to throwing that dream away, all because of his partying ways, McChrystal is grateful that West Point gave him a second chance.

He more than justified the Commandant Board’s decision.

“If there are things that really matter, value them,” McChrystal advised.

For McChrystal’s full interview with “Modern Wisdom,” click here.

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Originally reported by We Are The Mighty. Read the original article →
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