This American Snuck Out of His Dad’s House—and Got Bombed by Putin

POLTAVA, Ukraine—It was a one-in-a-million hit, said 23-year-old Skyler James Gregg from his hospital bed in Poltava, eastern Ukraine. He remembers how everything suddenly turned black when a Russian drone dropped an explosive at his post in the Kharkiv region on June 1. One French volunteer soldier died immediately in the blast, and flying shrapnel injured another foreign fighter.

Skyler was sent to the ground as fragments penetrated his body. One hit his right arm, tearing off a chunk of it. “It was all as black and white suddenly. It ran through my head that I might die. For some reason, it felt peaceful,” Skyler told The Daily Beast from his hospital bed.

“I felt heat in my arm. Dogs around were just screaming. It rang in my ears, and I ran to an outdoor bathroom and shut the door. I was trying to hold my arm together.”

After taking the hit, Skyler trudged outside with his shirt tied around his lower arm to hold it in place. He then locked eyes with one of his friends who had fallen down a set of stairs and was in a panic.

“He was losing a lot of blood. I took off his shirt to put pressure on his wounds. He was bleeding in so many places. I did not know what to do,” said Skyler. “I was about to faint myself. I took a plastic bag and put it on his bleeding chest. He had trouble breathing.”

After using a radio to call for help, Skyler and several other soldiers were taken to a field hospital. Skyler’s friend survived.

Poltava is a city in eastern Ukraine, about 200 kilometers from the frontline. Skyler sustained several injuries and still requires treatment at the hospital. Besides his right hand, about 14 fragments punctured other parts of his body, including his right foot and shoulder.

Originally from Orcas Island in Washington state, Skyler lived with his father before traveling to Ukraine. He’s one of dozens of American volunteers fighting in the Ukrainian army’s International Legion. It’s unclear exactly how many Americans have left to fight in Ukraine, and though the Biden administration has discouraged Americans from volunteering independently, it isn’t against the law to do so.

Recently, two American volunteer fighters from Alabama, 39-year-old Alexander John-Robert Drueke and 27-year-old Andy Tai Ngoc Huynh, went missing near the frontline in Kharkiv. They are feared to have been captured by Russia, where some argue they could face the death penalty.

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But that doesn’t seem to phase Skyler, who told The Daily Beast he intends to go back to fight as soon as he is recovered. “The job isn’t finished,” he said. “I have not finished what I came to do.”

Skyler had an ordinary upbringing. He has family members who have served in wars and said that he felt a call to fight in Ukraine when he saw a video of a Russian tank driving over a civilian car. The brutality struck him, he said, and he couldn’t just sit by.

In April, he packed his bags and snuck out of his father’s house early one morning, then took a bus to meet his mother, who drove him to the airport. His father had been against him leaving, arguing that he should find other ways to help. His mother, however, supported her son's decision to support the Ukrainian fight for independence, Skyler said.

“He must have sneaked out when I was not around,” Skyler’s father Steve told The Daily Beast. “I didn’t want him to go without any military experience, without a support system and even without knowing the language. I did not want to encourage him.”

When he found out that Skyler had made it to Ukraine, Steve posted the words of Colonel Ludlow from the World War I movie Legends of the Fall on his Facebook in April. “My dear lsabel, today our sons are leaving home to defend an England they have never seen. I am unable to stop them. l have tried to shelter our sons from all the madness. And now they go to seek it,” the quote read.

“Skyler told me that he wanted to be a medic, to help people,” said Steve. “That he wanted to be something between Desmond Doss in the movie Hacksaw Ridge and the soldiers in Saving Private Ryan. I can admire that but I still didn’t want him to go.”

Skyler had previously studied in Poland and has friends in Ukraine. He told The Daily Beast that he has experience handling weapons but doesn’t have any military experience, which is a requirement for joining the International Legion in Ukraine. But nobody checked his experience level at the time, he said, and he found himself in a training camp in Ukraine in April. He attributes the ease to which he was able to volunteer to the fact that he joined in the early days of the war, when everything was new and chaotic.

“I didn’t want to seem more experienced than I really was, so I just told them that I had the bare minimum experience,” Skyler said.

Ukraine’s International Legion did not respond to requests for comment from The Daily Beast about Skyler’s situation by the given deadline.

At the training camp, Skyler said he was told he would spend “the first day at the firing range, the second learning tactics, and the third with helicopter training,” all of which would be taught by former American special forces.

But according to Skyler, it didn’t happen exactly like that. He said he was assigned to the position of machine gunner, equipped with an LMG machine gun. He left training two weeks later without ever having fired a shot at training, he told The Daily Beast.

“It was quite disorganized, but that was how it was back then. Nobody knew how the war would unfold, and there was a need for volunteers,” he said.

Skyler was sent to Kharkiv in eastern Ukraine in mid-April. The city was experiencing heavy fighting around its outskirts and the Russians pushed to take control. Skyler and the others spent two weeks at a base, practicing how to storm houses in captured villages where Russian soldiers might be.

“There was a lot of dust in the building. It made me very sick. My lungs were kind of not really working properly, and I was very dehydrated as we lacked supplies,” said Skyler, who said he saw several of his colleagues leave the battalion at that point.

“I think that some people just had different expectations of this war,” said Skyler. But he decided to stay.

“Let me tell you, [Skyler] was one of the guys who stayed with us no matter what. He was fulfilling his duties and never made problems. When some left, he stayed and did his job,” German Barin, Skyler’s former Platoon Commander at the International Legion, told The Daily Beast.

After his time at the base in Kharkiv, he was moved to forward positions at the frontline, with the job of ensuring that the Russian army wouldn’t cross a river. He spent days looking at the Russian positions through night vision and monoculars. The Russians never came, and Skyler spent most of the time waiting.

The Russians were shelling the area the day before Skyler was wounded. That day, he took a video with the sound close in which he can be heard saying “Russians can’t aim.” The very next day, they did.

“To be honest, we were too relaxed,” said Skyler, who admitted he had become too confident that the Russians would never hit their positions. “So, we were like ‘they can’t hit us.’ But that all changed the next day.”

Skyler understands that some people might hear his story and think it was a stupid decision to go in the first place, and that he should have tried to help in other ways. His father argued the same before he left, but Skyler still feels he made the right decision. “I was just so angry… I wanted to stop what was happening, not just make what is happening less miserable,” he said.

Across the Atlantic, Steve still feels that it wasn’t the right decision for his son to go to Ukraine. He said that he knows that young boys do stupid things to gain the approval of their fathers and he just hope that Skyler isn’t in Ukraine to prove anything to him.

“For me, nothing has changed. I still love Skyler as much as ever, but he has gone to a place where I can’t help him and it is difficult,” said Steve. “I sometimes feel like I should buy a plane ticket and go there to help him but I know that isn’t a good idea. It is hard.”

While he might not approve of Skyler’s decision, Steve will still welcome him with open arms. “I am very proud of my son,” he said. “Even though he is going about things a little differently than I expected.”