The Hardest Risk
Winston sat in the back of the black SUV, watching the rain lash against the sugarcane fields outside his window. The road to the airport was a familiar one. He had traveled it hundreds of times over four decades. But today, the weight in his chest was heavier than usual. At seventy-two, Winston was the longest-serving CEO in the Caribbean insurance industry. He had started as a young man with a polyester tie and a leather satchel, knocking on doors in the sweltering heat of Port of Spain, selling life policies to housewives and taxi drivers who looked at him like he was selling snake oil. "Young man," an old fisherman had once told him, squinting through the smoke of his cigarette, "you want me to buy insurance against death? When I die, I dead. What I need money for?" Winston had laughed then, a nervous, boyish laugh. He had not known how to answer. He only knew that he needed the commission to pay for his mother's medical bills. Now, he knew the answer. He ha...