People of Eastern: A conversation with Tiger Winston, who shares his conversation adventures

By: Christian Lengkeek

At five o’clock on a Sunday, I met with Tiger Winston in Baird Library where we talked for over an hour. I highly doubt my ability to capture that whole hour accurately in a few hundred words, so this will be only a shadow of the color and personality of his actual story.

It all began on a Thanksgiving day in high school when he was returning from the Grand Canyon with his family. They had just stopped for the third time that day at McDonalds (much to Tiger’s disappointment). As he was walking through the parking lot he noticed a homeless man, and partially on a whim, but also partially out of guilt since he had just been complaining, he decided to offer to pay for the man’s meal. The man was very appreciative, and so they went inside together. Once outside again the man only ate a part of the meal, and when Tiger asked the man if he wasn’t hungry, he replied, “No, I am going to bring it home to my family for Thanksgiving.” Tiger describes this as “The moment the reality of homelessness clicked in my head.”

The next Thanksgiving, Tiger found himself alone in Long Island. Remembering the previous year, he decided to head into New York city and see if he could repeat his experience. This time he was able to buy meals for multiple people, but more than just buying them meals, he attempted to hold conversations with them. This desire came from a story he had heard from his pastor about a homeless man crying after being hugged for the first time in years. Tiger said, “The homeless rarely receive attention or love. I really just wanted to give that to people, much more than the food.” At first he just bought stuff for people because he found talking “a bit nerve-racking,” but after his first conversation with a man named Mike, talking became much easier. 

Talking to people who are often overlooked has become Tiger’s main objective. Throughout his last years of high school and his first year of college, he has made these trips a much more regular part of his life. He describred the people he speaks with as “people who are so down in life but also have so much hope.” He said he has heard some of the most painful stories in these conversations, stories about lives that have fallen apart, many because they were rejected or abandoned by their family and friends. 

Because of the homeless person’s overlooked perspective on life, Tiger finishes every conversation by asking who ever he has been chatting with for advice. Often the advice he receives centers around the idea of “keep pushing” or, more generally, perseverance. Since then, as he has expanded to talking with more and more people, he has begun asking just random people he runs into for life advice. Even with a broader audience, the the theme of perseverance has remained, he also has added the question “What makes you happy?” He has found answers to this question (he is currently compiling a list) often ended up being centered around people. Tiger said, “I thought this was really cool. Life is really about people. Even people who want to be billionaires, its often because they want to spend the money on themselves or their family. Everything seems to point back to people.”  

It may seem that Tiger is some gifted extrovert, but he claims that for most of his life he was shy and didn’t do a lot of talking. It wasn’t until he forced himself to speak to strangers that he began to get over his fears. When I asked how to best start talking to random people, he said, “Once I did it the first time, it became really easy.” Multiple times during the conversation Tiger emphizied the value of listening, specifically listening to those who are not heard. From his conversations, he has encountered people who actually have no one who listens to them. He hopes that perhaps these tiny moments might bring them the bit of joy they need to persevere.