In 1933, the Great Depression took a toll on the School. The Hagerstown Bank, which had held the School's funds since 1842, went out of business, and rumors about Saint James closing its doors began to spread.
That same year, the Saint James treasurer disappeared with $16,000 of the School's money. Sadly, Adrian Onderdonk was blamed for this mishap. Amidst pressure from the Board of Trustees and economic struggles, Onderdonk resigned in 1939. He remained at the School as the Latin Master, while James Drake became Headmaster on an interim basis.
According to Stevenson W. Webster, Adrian Onderdonk was, "A man of firm character and splendid personality; he fostered in the school a background of integrity and accomplishment and an atmosphere of loyalty and devotion. Few who came into contact with him...were uninfluenced by the association. He was a fine man and an outstanding headmaster."