Barry Sloane, second-generation Chairman, President, and CEO of his family's bank, Century Bank, weighed whether to sell to Eastern Bank. As a small regional bank, Century faced a number of challenging trends, such as digitization and market share decline in the coming years, despite its past decade of top performance, balanced growth, and careful risk management. Whereas his father consistently refused to sell during his lifetime, Sloane worried this might be the last cash offer on the table for the bank. On the other hand, selling was an irreversible decision that would severe the family's legacy and the next generation from the bank. Was it finally time for the Sloane family to part with Century Bank?