Fukushima Masanori
After Hideyoshi died in 1598, leaving his five-year-old son Hideyori as his successor and Tokugawa Ieyasu moved to take control. As he was very close to Hideyoshi, Ukita naturally sided with the Toyotomi loyalists under Ishida Mitsunari (the Western army). He took 17,000 men to fight in the Battle of Sekigahara. His army fought against Fukushima Masanori in what is said to have been one of the bloodiest confrontations in the battle. Ukita's troops were winning the battle, pushing back Masanori's army however, being unaware that his allies stationed nearby had made a secret deal with the enemy, his momentum was halted when his allies attacked and together with turncoats, Masanori's army took control of and eastern army won the battle.