A South Carolina couple’s romantic journey took an unexpected twist in New York City when a failed marriage proposal led to a rescue mission involving the city’s utilities and transit agencies. Chasmon Wilson, a truck driver from Roebuck, SC, brought his girlfriend of eight years, Kayla Pressley, to the bustling heart of Midtown Manhattan, Times Square, on a rainy Saturday in March with a $1,600 princess-cut diamond engagement ring in hand, planning to propose.
As Wilson pulled out the small Kay Jewelers box, the ring popped out and fell through a sidewalk grate, plummeting 20 feet down to a ledge covered in trash. It was like everything moved in slow motion,” Wilson told The Post. I was in disbelief that this is what we came to New York for and it fell through. I felt like the worst man on planet Earth.
Wilson had initially planned to propose at One Vanderbilt, a skyscraper offering panoramic views of Midtown Manhattan, but got “cold feet” when confronted with the throngs of people in Times Square. Pressley, who had been with Wilson for nearly eight years, was unaware that this day marked their engagement and missed the ring’s fall while putting their umbrellas away.
Wilson initially misled her, claiming he dropped a hotel key card. However, his dramatic reaction and efforts to retrieve it tipped Pressley off about the real nature of the lost item.
A stroke of luck came in the form of a Consolidated Edison (Con Ed) truck that happened to pass by, allowing Wilson to flag it down for assistance. Con Ed’s Elvimar Rivas, a senior analyst at the company, and his team quickly determined that the grate was not part of their infrastructure but rather belonged to the Metropolitan Transportation Authority (MTA.
Although initially pessimistic about recovering the ring, Wilson and Pressley returned home with their children Grayson, 7, and Skylar, 6, to Roebuck, SC. Unbeknownst to them, Rivas reached out to the MTA over the weekend, hatching a plan to rescue the lost engagement ring from its 20-foot fall in the heart of Manhattan’s busy streets.
A crew of five was dispatched to assess the situation and another team of five was deployed to retrieve the precious bauble beneath Seventh Avenue near West 46th Street. The recovery operation had to be conducted overnight to avoid any disruptions from pedestrians or traffic.
Rivas expressed immense satisfaction with the successful rescue, saying, “It made my whole year, just being able to help somebody recover a ring, especially in Times Square. That’s near impossible to do.
Approximately a week later, Wilson received a text message informing him that the engagement ring had been recovered. However, by the time it arrived back home in South Carolina, Wilson had already purchased a new, slightly different, engagement ring and proposed to Pressley on April 27, far from any sidewalk grates. The couple chose to exchange vows atop Stone Mountain in Cleveland, SC.
The ordeal has left a lasting impact on the devout Christian couple, who now believe that their engagement unfolded according to God’s plan and timing. Pressley plans to keep both engagement rings as reminders of the unique story behind their love and commitment. As for Wilson, he is leaving the wedding planning responsibilities entirely up to his fiancée in anticipation of their special day on May 24, 2025.
