Said to have been born in Ōmi (Shiga) (birthplace and year debated).
Around this time he entered Hashiba Hideyoshi's service and became close to fellow retainer Ishida Mitsunari.
He distinguished himself at Shizugatake. Hideyoshi later reportedly said he would like to see him command a million men.
Granted Tsuruga in Echizen, he became a daimyō. He excelled at logistics and administration.
In the Bunroku campaign he was charged with ships and supplies alongside Ishida Mitsunari, and crossed to Korea himself.
From around this time he suffered a grave illness and reportedly covered his face with cloth. A tale says that at a tea gathering Mitsunari drank the tea others shunned after Yoshitsugu.
He meant to side with Tokugawa Ieyasu, but Mitsunari confided his plan to strike Ieyasu. He warned there was no chance of victory, yet, seeing his friend's resolve, joined the Western Army out of friendship.
At Sekigahara he had prepared for Kobayakawa Hideaki's betrayal, but other units defected too and his army collapsed. Yoshitsugu took his own life on the battlefield.
Tokugawa IeyasuIshida MitsunariKobayakawa HideakiSanada Yukimura (Nobushige)
Katō YoshiakiHosokawa TadaokiWilliam Adams (Miura Anjin)Ikeda TerumasaDate MasamuneSanada Yukimura (Nobushige)Tachibana MuneshigeKuroda Nagamasa
People of the Sengoku/Azuchi-Momoyama period ・ People by period
Based on facts found in textbooks and biographies. Uncertain points are marked as such.