H is for Helping the Homeless

When I first met Blue a year ago, I wasn’t sure what to expect. There he was, a soft-spoken man on a bustling street corner in NYC, holding a sign asking for money.

Little did I know that this chance encounter would lead to a saga that would forever change my understanding of generosity, redemption, and service.

Three Questions Pondered:

As our interview began, Blue quickly shared his story with me. Growing up in the New Orleans projects, he followed his uncle into the family business of selling drugs.

One day, after being robbed by a customer, he was pressured by his family to retaliate. A couple of weeks later, he found the man at a local block party and, in cold blood, shot him in the back of the head.

He was 17 at the time and spent the next 18 years behind bars, getting out when he was 35. He was 45 when I met him, a vagabond traveling around the country, moving from city to city.

“Do you feel guilty about it?”, I asked. 

“I killed a guy. He won’t, he’s never coming back.”

“Do you ever pray about it?”

“Every night, dude. I pray for forgiveness.”

I had never interviewed a murderer before and was conflicted. On the one hand, I felt bad that he had spent the best years of his life in prison, and on the other, I couldn’t fathom how he could kill someone.

Nevertheless, my compassion overrode my internal conflict. I wanted to help him, and in the weeks and months to come, I would frequently visit Blue and his traveling companion, Phil, giving them money, food, and, at one point, a pair of Bibles. Over time, a friendship began to develop.

The Dilemma of Generosity

Then, one day, I got a text from Phil saying they needed help.

They’re trying to get out of NYC but can’t seem to save up enough money. They feel bad asking for help, but they’re trapped in the city and desperate.

I had already given them a good chunk of change, but knowing I was their only source of support, I felt obligated to help.

With the assistance of my followers, we quickly raised $800 to buy Phil and Blue a pair of bus tickets, one night’s lodging, and give them some extra cash to get them situated in Philadelphia, their next city. 

The following day, in a grand gesture of generosity, I gave them the money in a closed envelope. Phil broke down.

“Growing up I always got made fun of, never had nice clothes or nice anything. And here are these people, who don’t even know me, helping us out.” 

It felt good to see generosity change hearts. I felt warm inside, like I had done a good deed. I also felt relieved knowing that once they left New York, I would no longer have them under my responsibility.

After the pair left for Philadelphia, I didn’t hear from either for a couple of months when suddenly, one day, I got a text from Phil. He caught pneumonia and was staying at a hospital in Philadelphia. Blue and him separated after getting into a fight where Blue punched him. Fearing for his life, Phil ran away.

I was shocked. I thought I knew Phil and Blue well enough to trust and want to help them, but now I wasn’t so sure. I began wondering if I should have ever helped in the first place.

After Phil left the hospital, there was more radio silence for a couple of months. I began to chalk up the whole thing as a learning experience to think twice before helping others, when one day, I’m walking around the city and see this:

Blue had come back to New York by himself. Wary of his intentions, I dug into what happened with him and Phil.

Apparently, Phil wanted to buy drugs, and Blue was against it, eventually getting physical. He regretted hitting Phil and, when pressed, admitted to an anger problem that likely stemmed from his traumatic upbringing and past. I began to trust Blue again.

Blue was sad to lose Phil. The two had been traveling companions for several years and formed a deep bond, something Blue didn’t have much of in his life.

Losing Phil made Blue rethink his vagabond life. He had gotten a taste of real friendship and connection and, for the first time in a very long while, had dreams of getting off the streets, getting a real job, and becoming a part of society. 

It’s rare to meet someone who genuinely wants to change, so I told Blue I was committed to helping him. “I got to believe,” I said, “that between you, me, and God, we’ve got to be able to make this work. Right?” 

“Right.”, he said.

We shook on it. 

The Redemption Journey: Take One

In what seemed like a miracle, less than a week after our handshake, Blue told me he had reconnected with an old friend who ran a construction company in Denver.

Blue told his friend about his recent change of heart, and his friend told him to come over. He could give him a job at his company and housing. He even bought Blue a cross-country bus ticket to show his seriousness. 

Things were coming together for Blue. We bought Blue everything he’d need for a construction job in Denver. Clothes, tools, a pair of boots. Similar to Philadelphia, in another grand gesture of generosity and goodwill, I sent Blue off to Denver, once again relieved that he was off my hands.

Upon arriving in Denver, Blue’s friend started avoiding him, and it soon became apparent that the whole thing was a scam. His friend had used him for tax write-off purposes, and now Blue was stranded, walking the streets of Denver in the dead of winter. 

Blue eventually bumps into some Christian street missionaries who direct him to a nearby shelter. One night at the shelter, one of the other occupants steals Blue’s phone. They get into a fight. Blue pulls out a knife and cuts the guy, slashing the man across his lower cheek, narrowly missing his throat. 

The cops quickly arrive and take Blue to jail, where Blue calls me and tells me everything that’s happened.

Once again, I was shocked and filled with conflicting emotions….

On one hand I was angry and disappointed in Blue. Before he left for Denver, I had told him to watch out for his anger problem.

On the other hand, I felt partly responsible. I should have vetted the opportunity more. Did I really think the job and his friend were legit? Or was I just eager to send Blue off so he would no longer have to depend on me?

While I wasn’t sure of my true motivations, what was clear was that Blue was now more dependent on me than ever before. 

The Crucible

He was facing a potential felony of up to 7 years in prison, maybe more if the DA felt so inclined. I acted as Blue’s advocate, getting on calls with his public defender to discuss Blue’s case and pressing her to do what she could to help Blue. 

Meanwhile, Blue and I were texting back and forth. I sent him money every month and had check-in calls every Saturday. I told him to lean on God, and to use this opportunity while he was behind bars to begin journaling, praying, and reading the Bible to get his mind and spirit right.

The whole thing was a wake-up call for Blue. Faced with the possibility of losing another chunk of his life to prison, his dream of getting off the streets and becoming a regular member of society was in serious jeopardy. He began to realize that his margin for error in life was razor-thin and that he needed to stay firmly on course.

Throughout all of this, Blue leaned on God. The foundations of Blue’s faith were built during these months. In the midst of trial and tribulation, Blue learned to find peace in God, and in turn was given newfound levels of hope and resilience. 

The Redemption Journey: Take Two

After spending nearly six months behind bars, with various pre-trial legal proceedings that I didn’t fully understand, one day, I got a surprising text from Blue.

The victim didn’t want to participate in a trial, so the DA dropped all the charges. There wouldn’t be a trial, and Blue wouldn’t have anything on his record. He’d be let out in two weeks. 

I breathed a sigh of relief. Hallelujah, Blue was going to be okay. 

Blue arrived back in New York on a Sunday. We met up, hugged, and caught up. He was a changed man—even more mellow and humble but also more focused with a quiet determination.

Once again, I had mixed emotions. On one hand, I was happy to have him back, but on the other, I felt burdened. Instead of keeping my mixed emotions to myself however, I communicated how I felt as tactfully as possible. Blue was empathetic.

I started discovering a generosity that is driven more by connection than guilt and seeing generosity as a dynamic process, a journey in and of itself.

That same day, I brought him to the afternoon service at my church, where he gave his life to Jesus. Later that evening, as we walked around the streets of New York, Blue bumped into an old homeless friend who had recently secured free housing through a city program. 

Through this connection, Blue was able to contact the same organization, and within a couple of days, he, too, found a place to stay: a shared room in a housing complex in the Bronx.

Not exactly the Sheraton, but the fact that he had secured free housing within days of arriving in the city was nothing short of a miracle. Now, with a roof over his head, the next steps were securing food stamps, getting his paperwork in order, and finding a job.

Blue’s dream of getting off the streets and becoming a contributing member of society was starting to come true.

Three Questions Pondered — Speculations

💡 More than we think, but it’s a balance. We should aim for a generosity deeply connected with our own well-being and the well-being of others, we should aim for a generosity driven by connection and not guilt.

💡 First, the person must genuinely want to change.

Then, through patient, consistent acts of love rather than grand gestures, we water the soil from which true transformation and heart change come from the Lord.

This is a mysterious process.

💡 To be sure, this is still the start of Blue’s journey. We know that there are many challenges, obstacles, and lessons to come. But given everything that has happened and how much Blue has changed, I want to say that, generally speaking, no, nobody is ever too far gone to turn their life around. All one needs is a mustard seed.

Throughout this saga, what has been clear to me is that despite whatever limitations humans may have in helping another, God has no such restriction.

Our God is a God who goes after the lost, hard.

That Blue and I met when we had, that things transpired the way they had, that God watched over us through it all.

God has etched a story of redemption on the hearts of all of mankind, and if He wants to save someone, He will do just that.

It’s been almost a month since Blue has been in the city. There are days it’s hard to support him, there are days I feel like I should be doing more, and that’s okay. In the end I know it’s not my job to save Blue, it’s my job to just keep showing up, and I hope you do too, for the Blues in your life.

With curiosity,

Eric

P.S. I am making a YouTube video of this whole saga, with cartoon animations, effects and more backstory on Phil and Blue. Look out for a video in the coming months. 

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