A Simple Twist of Fate- Behind the Scenes of Kenny Chesney’s Knowing You Video (Part 1/3)

On Friday, March 12, Kenny Chesney released a new music video entitled “Knowing You” that was filmed partially in Gloucester, MA and partially on the Virgin Island of St. Croix and in her surrounding waters. The video is a bittersweet love story from the eyes of a sailor in which the Pop Country super star reflects from chilly New England back on the memories he created with a beautiful free spirit in a very different time with a very different backdrop.

Even though the video was filmed on St. Croix and not on St. John, the iconic artist never ceases with his love affair for Love City and selected his beautiful co-star from his circles here. Through these same circles, this young woman also found the boat, Sailing Vessel Kai, for him to use in this video. A vessel that was coincidentally making her way back to the USVI after spending the fall in a boatyard in the same New England mariner town where the first part of this video was filmed.

Last week, the lovely co-star from “Knowing You,” Monica Knaggs, Kai’s First Mate for the journey south, Sarah Ford, and myself hopped aboard Asante with my boyfriend, Captain Teddy, who also sailed south on Kai and was kind enough to play taxi for the three of us for the day. 🙂

We left Great Cruz Bay and headed out to Christmas Cove to meet up with the 70-foot sailboat, Kai, and her Captain/Owner, Justin Smith. Monica, Sarah, Justin and I sat down in the beautifully appointed salon of Kai so I could get the story from the three of them about how they became a part of “Knowing You,” their journeys to St. Croix and their experiences working with Kenny Chesney and his team.

This is a synchronistic, three-part story of how the boat, the girl and the musician came together to create this video that, in the end, reflects a calm after the storm.

On October 28, 2020, Monica Knaggs and her boyfriend, Connor Masterson, were at St. John Hardware picking up some parts for the boat that they were refurbishing. On their way out she received a text from Kenny Chesney that said “Ya got a sec to chat?”

She knew Kenny through Love City circles, but was bewildered as to why he would be randomly reaching out to her…She called the number from the car and put him on speaker phone, making the call with Connor. After a polite exchange, the pop country star explained to Monica and Connor that he would be shooting a music video in St. Croix a few weeks later. That he was looking for a specific type of authentic woman to fit his creative vision. She fit the bill and was she interested in being involved?

“It’s about a girl and a guy and they’re in love…,” Kenny said. “So of course I would have to ask Connor’s permission.”

A green light from Connor was given with the stipulation that he got to come along and Monica agreed to be Kenny’s co-star for the upcoming filming.

Kenny’s relationship with Connor stems back to Hurricane Irma. Connor was one of several St. John residents who sought shelter in Kenny’s home during the super storm of 2017. When Kenny’s helicopter arrived in the days following, Connor was there to help distribute generators and chainsaws used to clear the roads. In the years following, Connor continued to work for Chesney’s Love for Love City Foundation to help rebuild the homes of less fortunate individuals on St. John. Over the years Connor and Kenny became close friends and he and Monica would join Kenny on his boat or for drinks on occasion. When Kenny conceptualized the image of the woman he wanted in the upcoming video, apparently Monica came to mind.

So, she got the call, agreed to star in her first on screen performance and phone calls from the producers started to roll in so they could iron out details.

Now that Monica was locked in, there was another missing piece. Kenny needed a sailboat. Connor, a long time Captain and member of the boating community on St. John, was charged with this task by Kenny’s film crew. And he was having a tough time finding one that would fit the bill. A few days later, Monica noticed a friend’s Instagram post with a picture of a beautiful sailboat that had sought shelter in the states from potential hurricanes during storm season. This boat was about to head south and home to the USVI.

She texted Alex Dooley, a friend and St. John boat captain who was aboard Kai in Cape Lookout, NC. He, Ted Jennings Jr., Tyler Nance, Sarah and Justin were tucked into a safe haven waiting out weather and fixing the main halyard. While in the boatyard in Gloucester, Justin, Sarah and Teddy had installed a new sail that wasn’t a perfect fit. Inching their way south to avoid weather along the way from their previous ports of Connecticut and then Virginia Beach, the halyard snapped as they rounded Cape Hatteras. On Halloween, they tucked into Cape Lookout to make repairs and examine the weather patterns before heading east towards Bermuda and then south towards home.

If they hadn’t been forced to stop for a few days, they would have been off shore and Alex never would have received the November 1 message from Monica…Could Kai could make it to St. Croix in time for the filming of “Knowing You” on November 14?

“I remember Dooley getting the message,” Sarah said. “Justin was asleep already but we were up cooking pork for the trip south that night. He was like ‘Dude, you’re not going to believe what this text is about…Kenny wants to book the boat for a music video!’”

They hoped Justin would be on board.

The next morning the crew and captain sat down on a beautifully chilly and crisp morning with 50-60 mph winds whipping around outside the warm confines of Kai’s salon. The captain was, indeed, on board. And after an intense discussion about weather windows and warnings along the way, the crew enthusiastically agreed. But, in order to make it to both St. Croix on time and take advantage of the weather window, they had to make the call to go that afternoon.

“I didn’t really totally believe that Kenny Chesney was going to be in St. Croix when we got there,” Justin laughed. But he spoke with Kenny’s people, gave them the information for tracking and communicating with him via satellite phone while the boat was off-shore, looked at his four crew members and said: “Alright, let’s go south.”

But, first they had to fix the halyard. So, while anchored in winds nearing 60 knots, they hoisted their youngest mate, Tyler, up the 91-foot mast to replace the halyard with a spare that they had on board. When the halyard snapped and the sail came crashing down, it, unbeknownst to the Captain and crew, had broke an assortment of attachments to the mast. And so, during the repair process, Sarah and Dooley started to hear a small noise coming from inside of the mast. She recalled it sounded like pebbles dropping. Moments later, the line holding Tyler snapped and the young sailor fell several feet from the top, leaving the safety line to catch him and save him from a treacherous fall.

After multiple sighs of relief and a ton of man (and woman) power, the halyard was repaired and the main sail hoisted. A few hours later, the winds dropped to 30-40mph. And Kai sailed out of Cape Lookout with the wind at their back while Category 4 Hurricane Eta whipped at the Gulf Coast just to the southwest and another strong system moved towards them from the USVI…