John Neal described Watkins as "both generous and extravagant" in that he "would sooner empty his pockets into the lap of a stranger, than pay his butcher or grocer." Neal blamed this character trait for what he saw as Watkins "always laboring under embarrassment, up to the day of his death," citing that at the time of his appointment to the US Spanish Diplomatic Commission Watkins was on the brink of economic ruin by his own mismanagement of his family's funds.
