In 1877 Blakelock married Cora Rebecca Bailey; they had nine children. In art, Blakelock was a genius, yet, in business dealings and in monetary transactions he proved a failure. He found it difficult, if not crushing to maintain and support his wife and children. In desperation he found himself selling his paintings for extremely low prices, far beneath their known worth. In hopes of lifting his family from abject poverty, reportedly on the day his 9th child was born, Blakelock had offered a painting to a collector for $1000. The collector made a counter offer and after refusing the proposed sum Blakelock found himself in a bitter argument with his wife. After the domestic dispute, Blakelock returned to the patron and sold the painting for a much lesser sum. Defeated and frustrated, it is said he broke down and tore the cash into pieces. And so it was after such repeated failed business transactions that he began to suffer from extreme depression and eventually show symptoms of mental frailty.