PORTLAND PRESS HERALD • November 28, 2025
For more than 100 days, he had been winning his battles against the world’s fiercest seas and most of the other 15 sailors he was racing around the globe. Never before, in all those wet, cold, sleepless nights, had he truly been afraid. Now, as a massive storm hurdled toward the spot where he bobbed some 700 miles off the coast of Argentina, it seemed that all was lost. The race. His dream of completing a solo lap of the planet. The partner waiting for him back in Maine. It took something approaching a miracle — technological and otherwise — for Simpson to be rescued that day in February 2024. It’s something else that has compelled him to try it all over again. In 2027, Simpson plans to compete in the second-ever Global Solo Challenge, an around-the-world race that pits sailors against each other, the elements and the limits of their own will to endure. As he did two years ago, he will base his campaign in Portland, quietly the American epicenter of the little-known sport.