In 1577, Nagayoshi serving Nobutada to attack Matsunaga Danjo Hisahide in the Siege of Shigisan.

However, his campaign was forced to stop when his lord Oda Nobunaga and Nobutada died at Honno-ji incident.

Later, Nagayoshi took Mino Castle with the help of his relatives from the Ikeda clan side of his family.

In 1584, Nagayoshi's efforts for Toyotomi Hideyoshi during the difficult Battle of Komaki and Nagakute ultimately took his life.

[3] He stood out conspicuously wearing a white jinbaori and was subsequently shot in the head by Tokugawa ashigaru firing a matchlock rifle.