Born from the sea
Built for family
A legacy passed down
Before Will 2 Win became a premier five-vessel fleet, it was a family tradition. Jeremy first fell in love with the magic of Cabo San Lucas the way so many do: out on the water with his family, experiencing the unmatched thrill of the offshore bite. That obsession didn't just stick, it grew. That passion has been passed down to his kids, who have stepped onto leaderboards and won tournaments since they were young.
A Twist of fate & perfect bad weather
The true turning point for the fleet came during a legendary maritime journey. Jeremy was bringing Will 2 Win’s new 80’ Viking down from Pensacola, Florida, to its permanent home in Cabo. Passing Puerto Aventuras, Mexico, Jeremy insisted on dropping anchor for a few days so his captain, Scott Flores, could visit his mother, Tonya.
As fate would have it, Tonya and Anne Marie were friends. She brought Anne Marie aboard to see the beautiful vessel and meet her son. That afternoon, Jeremy and Anne Marie wound up spending two straight hours on the bow, playing fetch with Jeremy’s new 13-week-old puppy named Frannie, just talking about life and the ocean.
Anne Marie was scheduled to fly out the next day, and Jeremy was only supposed to stay for a 72-hour window - they never expected their paths to cross again. But the ocean had other plans. A sudden stretch of heavy weather kept the boat in port longer. By the time Anne Marie returned a week later, Jeremy had unknowingly befriended her circle of friends. They fell in love, she came along for the ride, and they never looked back.
Our Core Focus, OuR Home
Today, Cabo San Lucas isn’t just a destination on a map for us, we’ve made it our home, our community, and our core focus. We live here, managing every aspect of the operation with a hands-on dedication to building real, lifelong relationships with the families who step onto our docks. When you fish with Will 2 Win, you aren't just renting a boat for the day: you are joining a family tradition of excellence on the water.
