STT charter captain remembered for heroism following fatal crash

"He was just the biggest gem of a human"

In the aftermath of a horrific boat crash that killed 39-year-old Stephen Cross Jr., his fiancĂ© Caitie Rosko is sharing his story to spread awareness about speeding in mooring fields, in the hope of preventing a future tragedy. “He was just the biggest gem of a human,” Rosko said in an interview with The Daily News. “He changed not just my life, but everyone that he came in contact with.”
For nearly a decade, Cross and Rosko built an extraordinary life as experienced charter industry professionals living on St. Thomas.

When it came to his career as a captain, Rosko said Cross had a reputation for not taking any risks. 

“He was always the safety guy, ‘Slow is pro,’ was his motto,” Rosko said. “He had zero ego in that sense.”

In late November, they were each captaining separate catamarans around the British Virgin Islands — Rosko entertaining friends, and Cross working to give paying guests the vacation of a lifetime.

They met up in Anegada before going their separate ways, and Rosko headed home while Cross continued on to the North Sound.

Two days later, on Nov. 22, Cross and his guests were on a dinghy headed in to the small island of Saba Rock for happy hour and a fun evening.

While she was miles away at the time, Rosko said the guests have reached out to her and recounted what happened that night.

As he was driving slowly through the mooring field, a guest shouted, “look behind you!” and Cross turned to see a 21-foot aluminum hull inflatable boat speeding towards them.

It was around 6:30 p.m. and “a boat came flying out of nowhere in the dark doing like 20 mph in the mooring field,” Rosko said.

She said the larger yacht tender had a 150-horsepower engine and was twice the size of Cross’s dinghy, leaving him little time to react.

According to the guests, “he made a last-minute maneuver to turn the boat, to get them out of the way. But in doing so, the boat essentially went right over him,” Rosko said.

The guests were ejected from the dinghy and survived the crash, and “they said he 100% saved all their lives,” Rosko said.

“I know for a fact that instinct was like, ‘Get everybody out of the way,’” she said. “The guests are calling him a hero, for sure, they keep reaching out to me.”

Rosko said she has been struggling to make sense of the crash.

“In all mooring fields, in all channels, it’s a no-wake zone, so you shouldn’t be going fast enough to be creating a wave,” Rosko said.

Driving slowly through a mooring field should be common sense for boat captains, Rosko said, and compared it to driving a car through a crowded parking lot.

“It’s a no-brainer, this has been a rule for years, since the beginning of time. You just don’t speed in a parking lot, think of it that way,” Rosko said.

Rosko said she and other members of the boating community are urging captains to slow down, and put caution and safety above all.

“Unfortunately, I think this does happen more often than we think,” Rosko said.

She said in conversations with Saba Rock Resort manager Chris Winschel, “he has been an amazing person because he knows how bad it is, and he says every day he sees people flying through and being reckless.”

The resort is working to implement positive changes following the tragedy, including state-of-the-art CCTV cameras in the channel and mooring field, in an effort to protect the health and safety of guests.

While increased regulation, penalties, and enforcement could help combat speeding, Rosko said that more than anything, captains just need to be cautious and slow down.

The driver of the yacht tender involved in the fatal crash, Lesley Joubert, 36, was arrested on Nov. 23 and charged with manslaughter. Rosko said authorities have been investigating, and she is waiting for the case to proceed through the British Virgin Islands court system.

In the meantime, she has been grappling with grief amid an outpouring of support from friends, loved ones, and strangers who have reached out to share their memories of Cross.

Many have shared emotional remembrances on social media, pouring out touching tributes to a man who always went the extra mile to make sure everyone was having a good time.

“I met him about three months after I moved to St. Thomas,” in 2015, Rosko said, and “he convinced me to get my own kayak.”

At the time, “I barely snorkeled,” but soon they were going out paddling and free diving for lobster three to four times a week, and Cross would make a fire on the beach and cook meals from scratch.

Rosko said she often wondered, “is this real life?” as their friendship developed into a picture-perfect romance, and Cross went to captain school while she took culinary classes. They ended up working on catamarans together for years, and celebrated their engagement on Christmas in 2023.

“Now, I have my 100-ton captain’s license and I drive catamarans for money, and it’s all because he just took me under his wing,” Rosko said.

Cross had a way of gently teaching and lifting up everyone around him, and “he did it with love and ease,” Rosko said.

Since his death, friends and strangers have reached out to share their own stories of learning from Cross, “so many people, hundreds and hundreds of people I don’t even know,” Rosko said.

On Dec. 9, Cross was transported back to St. Thomas from the BVI where he was met on the border by a flotilla of boats, including the U.S. Coast Guard, joined by Rosko and Cross’ family.

Friends are also keeping Cross’ spirit alive through stickers with the sayings, “Steve would go,” and “Never miss one,” Rosko said, “because there wasn’t a single day in his life that he wouldn’t seize a moment,” and he was a lover of the islands’ frequent rainbows.

The phrase, “Never miss one,” means, “never miss a rainbow,” but also “never miss a good swell to go surfing, never miss a great day to do something with it,” Rosko said.

Cross “was a big surfer, so if there was a swell, even if he had to work, Steve would go,” Rosko said, and he loved to go for hikes to de-stress, gathering friends to join in an adventure.

“He would pack the cooler, get all the friends together, carry a 50-pound cooler down to Mermaid’s Chair in his arms because he wanted everyone to have a great day,” Rosko said. “If you’re ever contemplating doing something, Steve would. Get your butt off the couch and go.”

In terms of his legacy, “he’s making shock waves for sure, which is pretty awesome because when you’re with somebody, you don’t realize the impact that they make on people every single day,” Rosko said. “The one thing people kept saying about him is, ‘He’s a man for others.’ That seems to be the common consensus.”

Rosko owns a brokerage for crewed charters, and while she is taking some time off work, she plans to stay in the industry and continue captaining boats.

“He wouldn’t want me to stop doing that, especially because I really love it and he made me so passionate about it, and it’s just such an incredible job,” Rosko said. “You get to show people the beauty of these islands. And I’ll take them lobster diving, all the things that he taught me that I thought were so freaking cool, I feel like I need to keep doing just because of him. He would want me to.” 

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