Family:
An Intergenerational Tradition
The year was 1943, and every Tuesday night, Jack would take his sailboat out into the dark waters surrounding Charleston, South Carolina. Being the fearless and resolved man he was, Jack was tasked with patrolling the harbor, looking for German submarines during World War Two. He called his sailboat The Riptide, and it was the first boat that his son, Lenny Krawcheck, ever had the privilege of sailing on. Lenny was just a baby during the war. But as soon as he was able to walk, he was planted beside Jack on The Riptide.
The patriarch of his middle class family, Jack worked long hours at his clothing store during the week. But every weekend, when the wind was rushing and the water was stirring, Jack would take his son to the harbor. Together they would prepare the boat, and begin their untroubled days on the water. Lenny looked up to his father, and on their outings, Jack taught him not only how to sail, but how to be a good man. In turn, his father bestowed his love of the sport onto him; and with that a family tradition began.
Lenny's father, Jack, sparked his interest, but soon enough his sailing took on a life of its own. He was only fifteen when he was working tirelessly at his father’s clothing store, in hopes of buying his very own sailboat. He and his older brother, Saul, pooled their money together, and bought a small two-man boat, which they sailed together for many years.
Saul helped Lenny to hone his craft. He taught him how to race a sailboat, which is a very different skill from sailing for pleasure. Soon enough, Lenny was competing in races with his very own crew. He was a natural leader on the boat, commanding his crew with a firm, yet amicable hand.
Lenny soon found himself with a family of his own, and a new era of his sailing life began. His wife, Townie, became his crew, and still to this day he says she is the best sailor he has been given the chance to sail with. All four of his children took sailing lessons, and the two boys, in particular, developed a real talent. His “little teammates,” as Lenny called them, took after their father, and grew to become accomplished sailors themselves. Whether it be in South Carolina, North Carolina, Florida, or Maine, the Krawcheck family traveled to whatever regatta was happening that weekend. The experience of sharing his passion with his entire family was an indescribable gift for Lenny, and the memories are held dearly by him, and all of his children.