He had always gotten a geshmak out of learning and enjoyed being in yeshivah, but after 12 years in the system, he’d started burning out. Unfortunately, Chesky had been so afraid that he’d be asked to leave if he admitted he wasn’t learning well, he’d kept it to himself.

Chesky hated himself for not being good enough, and since misery loves company, he found a small group of boys in the yeshivah who weren’t quite “good enough” either. Things quickly went from bad to worse, and Chesky was soon skipping seder and watching movies he’d downloaded onto his flip phone.

He was kicked out of yeshivah the same day he was caught, and he had been home ever since.

“I let everyone down,” he said in a choked voice. “My rebbeim, my parents….”

Yourself, I wanted to add.

Chesky’s insecurities were suffocating him. At 17, he believed that his life was over and that he’d never be able to bounce back — but I could see how much potential he had.

The question was how to get Chesky to see it.

Mr. and Mrs. Shulman, who had been hovering outside the doorway, knocked lightly on the wall and came in.

“We know you have relationships with a lot of rebbeim and roshei yeshivah,” his father said. “Is there a chance you know any of the hanhalah at Chesky’s yeshivah?”

I was about to shake my head when I realized that the rosh yeshivah was my second cousin.

“As a matter of fact, I do,” I told Chesky’s parents. “I’ll give the rosh yeshivah a call, if that’s okay with Chesky.”

He shrugged.

“We’re going to fix this,” I assured Chesky before I left, but he didn’t seem to hear me.

As soon as I got home, I emailed my rebbi, a gadol b’Yisrael, for guidance. The subject line read: Crisis. Boy getting kicked out of yeshivah.

After discussing Chesky’s situation with my rebbi at length, I called my cousin Baruch Weinberg — the rosh yeshivah — and asked him if he could tell me what was going on.

“There’s nothing to tell,” he said firmly. “He was watching movies in the yeshivah dorms, so you can imagine what kind of influence he could have had on our boys if we let him stay another day.”

“I understand,” I replied honestly.

The rosh yeshivah did was best for the yeshivah as a whole when he kicked Chesky out, but for the other boys who were struggling, this was going to be very damaging. Seeing Chesky expelled would reinforce the mentality that they were beyond saving, and, instead of scaring them straight, it would make them better at hiding what they were doing. Even worse, if any of the boys had been thinking about getting help from someone at the yeshivah, they would be too afraid of being expelled themselves to come forward.

But Chesky was my main concern, and he was at risk — really at risk. This was a matter of sakanas nefashos: Chesky had to go back to yeshivah, or we were liable to lose a nefesh in Klal Yisrael.

“Reb Baruch,” I said, comfortable enough with my cousin to make a suggestion. “Would you consider turning Chesky’s expulsion into a suspension?”

After being expelled, many boys go on a downward spiral emotionally, mentally, and, of course, spiritually. But if Chesky was suspended — and on probation —he would be forced to shape up instead, I explained.

“Interesting idea,” the rosh yeshivah answered noncommittally.

I knew that meant no, but as a last-ditch effort, I ran through some of the ideas that my rebbi and I had discussed to help Chesky that could be a precondition for his reacceptance to yeshivah. (This is by no means a one-size-fits-all approach, but my rebbi felt in this case it would work.)

First of all, Chesky would need to go to therapy to address the issues contributing to what got him kicked out of yeshivah, as well as problems that had surfaced during his time at home. Over the course of his suspension, Chesky would attend three minyanim every day and learn three sedorim with chavrusas approved by Rabbi Weinberg.

If the rosh yeshivah heard good reports from Chesky’s parents and chavrusas, I proposed that Chesky be allowed back into the yeshivah. At first, only during the day, and then eventually back into the dorm as well.

Rabbi Weinberg listened intently, and he seemed to be considering the idea.

“We’ve never done something like this before,” he explained. “I just don’t know if it will work out…” His voice trailed off.

“Chesky has enormous potential,” I said. “Once he lets go of everything that’s holding him back and commits himself, he’s going to shteig.”

I could hear the rosh yeshivah let out a deep breath.

“Reb Baruch,” I said slowly, “I am guaranteeing you that Chesky will be one of the top bochurim in the yeshivah.”

I was confident that it was true.

“Let’s give it a try,” Rabbi Weinberg said.

Later that week, I went back to the Shulman home to see how Chesky felt about his probation and to discuss the rosh yeshivah’s requirements.

“I won’t be able to do it,” Chesky said glumly. “And I’ll be kicked out again before I even go back to yeshivah.”

Chesky had lost all belief in himself, but the people around him hadn’t, and proving that would be the first step in rebuilding his shattered self-esteem.

“You can, Chesky. If I didn’t think — no, if I didn’t know — you could do it, would I have brought up your case with one of our gedolei Yisrael?”

My rebbi would like to remain anonymous, but when Chesky heard his name, he looked at me wide-eyed.

“Did you really?”

“I did. I sent him an email saying that you getting kicked out of yeshivah was a crisis. Because it was. I asked him for guidance, and made sure that I was doing everything I could to help you.”

“But…” Chesky dropped his gaze and stared into his lap. “But I’m a bum,” he whispered. “Why did the rav care?”

“Chesky, you’re not a bum.” I put my hand on his arm. “He came up with this plan because he knew a boy like you could succeed.”

“Look at me, Chesky — you’re a holy neshamah with a holy tafkid, and you’re going to do great things. We can all feel it.”

Chesky gave me a half-hearted smile.

Chesky’s parents updated me a month later when he was back in yeshivah for seder, and a month after that when he was finally allowed back into the dorm. I knew Chesky was doing well, but I didn’t know how well until I saw my cousin Baruch at a family simchah six months later.

“Nu, how’s my talmid?” I asked him with a smile.

Tears filled the rosh yeshivah’s eyes. He grasped my shoulder.

“I didn’t believe you, Yossie,” he whispered, “but he’s the best bochur in our yeshivah.”

Brain Trust: Tips for parents of teens

Believe in second chances.

You play a central role in nurturing your teen’s self-esteem, especially after a setback. Open communication with educators and other professionals allows for targeted interventions tailored to your child’s needs, and your belief in him is a powerful motivator for success.

Yossie Strickman is the founder of Project TRUST, an initiative that offers comprehensive support to those navigating the dangers of technology, including exposure to improper content, unhealthy internet habits, and cyberbullying. He is based in Passaic, New Jersey, and speaks about safe technology use across the United States.

(Originally featured in Mishpacha, Issue 1006)