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Many attempts have been made to explain the reasoning behind Hideyoshi's efforts to conquer Korea. Some have suggested that he was intentionally bleeding away the power of the daimyo, so as to strengthen the security of the Toyotomi. This theory has always been rather popular but overlooks the fact that the majority of daimyo who would fight in Korea were staunch supporters of Hideyoshi, including Kato, Konishi, Mori, and Chosokabe. By way of comparison, some less trustworthy elements never set foot in Korea, including Tokugawa Ieyasu and Date Masamune. Another slightly different but comparably popular suggestion has Hideyoshi invading Korea to provide an outlet for his daimyo, lest they have the time to begin plotting against their new overlord. Both arguments are essentially sides of the same coin, and are both weakened by the fact that most of the daimyo east of Kyoto never saw a day of service on the Korean mainland. The most likely explanation for Hideyoshi's campaign on the Asian mainland, then, was the same driving force that had seen him to rise to become Kampaku and had intoxicated so many other would-be conquerors: ambition.  

Many attempts have been made to explain the reasoning behind Hideyoshi's efforts to conquer Korea. Some have suggested that he was intentionally bleeding away the power of the daimyo, so as to strengthen the security of the Toyotomi. This theory has always been rather popular but overlooks the fact that the majority of daimyo who would fight in Korea were staunch supporters of Hideyoshi, including Kato, Konishi, Mori, and Chosokabe. By way of comparison, some less trustworthy elements never set foot in Korea, including Tokugawa Ieyasu and Date Masamune. Another slightly different but comparably popular suggestion has Hideyoshi invading Korea to provide an outlet for his daimyo, lest they have the time to begin plotting against their new overlord. Both arguments are essentially sides of the same coin, and are both weakened by the fact that most of the daimyo east of Kyoto never saw a day of service on the Korean mainland. The most likely explanation for Hideyoshi's campaign on the Asian mainland, then, was the same driving force that had seen him to rise to become Kampaku and had intoxicated so many other would-be conquerors: ambition.  

Unfortunately for Hideyoshi's dreams of true ascendancy, the Korean expedition bogged down after initially impressive gains. In May Seoul had been occupied, and on 16 June [[Konishi Yukinaga]] marched into Pyongyang. At the same time, [[Kato Kiyomasa]] was driving hard up the eastern half of the peninsula and would even cross briefly into Manchuria. Within four months, then, Japanese forces had cleared a road into China. Three factors would combine to slam that door shut: Koran guerillas, the arrival of large numbers of Chinese troops around Pyongyang, and the Korean Navy, which under Admiral Yi Sun Shin proved almost invincible. Admiral Yi inflicted a series of naval defeats on the Japanese that cut deeply into Hideyoshi's logistical organization. Korean guerillas further harassed supply lines while tying down significant numbers of Japanese warriors behind the lines attempting to ferret them out. The Chinese, while not militarily the equal of the Japanese, outnumbered Konishi's command and forced him to retreat from Pyongyang in February to avoid being isolated. Kato had no choice but to retreat as well, and by July the operation was clearly stalemated and in danger of ultimately developing into a complete disaster. Hideyoshi found it wise to negotiate, and stated that he would agree to a peace if, among other things, a daughter of the Ming Emperor was given to the Emperor of Japan. The Chinese, while probably amazed at the audacity of that demand (which, needless to say, was never fulfilled), agreed to a ceasefire. Hideyoshi, whose forces still controlled some territory in Korea's southern-most province (Kyongsang), could boast to Luis Frois later that year that "he had already conquered the kingdom of Korea." and that the Chinese "had sent him their submission".<ref>Cooper. ''They Came to Japan.'' pg. 113</ref> He further demanded that Luzon show him obedience, threatening to invade if this was not done.  

Unfortunately for Hideyoshi's dreams of true ascendancy, the Korean expedition bogged down after initially impressive gains. In May Seoul had been occupied, and on 16 June [[Konishi Yukinaga]] marched into Pyongyang. At the same time, [[Kato Kiyomasa]] was driving hard up the eastern half of the peninsula and would even cross briefly into Manchuria. Within four months, then, Japanese forces had cleared a road into China. Three factors would combine to slam that door shut: Koran guerillas, the arrival of large numbers of Chinese troops around Pyongyang, and the Korean Navy, which under Admiral [[Yi Sun-Shin]] proved almost invincible. Admiral Yi inflicted a series of naval defeats on the Japanese that cut deeply into Hideyoshi's logistical organization. Korean guerillas further harassed supply lines while tying down significant numbers of Japanese warriors behind the lines attempting to ferret them out. The Chinese, while not militarily the equal of the Japanese, outnumbered Konishi's command and forced him to retreat from Pyongyang in February to avoid being isolated. Kato had no choice but to retreat as well, and by July the operation was clearly stalemated and in danger of ultimately developing into a complete disaster. Hideyoshi found it wise to negotiate, and stated that he would agree to a peace if, among other things, a daughter of the Ming Emperor was given to the Emperor of Japan. The Chinese, while probably amazed at the audacity of that demand (which, needless to say, was never fulfilled), agreed to a ceasefire. Hideyoshi, whose forces still controlled some territory in Korea's southern-most province (Kyongsang), could boast to Luis Frois later that year that "he had already conquered the kingdom of Korea." and that the Chinese "had sent him their submission".<ref>Cooper. ''They Came to Japan.'' pg. 113</ref> He further demanded that Luzon show him obedience, threatening to invade if this was not done.  

The birth of Hideyoshi's second son, [[Toyotomi Hideyori|Hideyori]], in 1593 both distracted the Taiko from the depressing results of his Korean misadventure and created another problem. The threatening clouds of a potential succession struggle must have haunted Hideyoshi, who had already named Hidetsugu heir and yet devoted himself to Hideyori. The matter was brutally decided in [[1595]], when in August Hidetsugu was exiled to [[Mount Koya]] and then ordered to commit suicide. Those of his family who did not follow suit were murdered en mass in Kyoto, including 31 women and a number of infant sons and daughters. The specific reasons behind Hidetsugu's fall are entirely unclear, so much more the reasons for the excessive brutality with which Hideyoshi treated the family. Scholars continue to make assertions regarding this event; in truth, the specifics will never be more then a matter of speculation, except that a possible succession dispute had been dealt with.  

The birth of Hideyoshi's second son, [[Toyotomi Hideyori|Hideyori]], in 1593 both distracted the Taiko from the depressing results of his Korean misadventure and created another problem. The threatening clouds of a potential succession struggle must have haunted Hideyoshi, who had already named Hidetsugu heir and yet devoted himself to Hideyori. The matter was brutally decided in [[1595]], when in August Hidetsugu was exiled to [[Mount Koya]] and then ordered to commit suicide. Those of his family who did not follow suit were murdered en mass in Kyoto, including 31 women and a number of infant sons and daughters. The specific reasons behind Hidetsugu's fall are entirely unclear, so much more the reasons for the excessive brutality with which Hideyoshi treated the family. Scholars continue to make assertions regarding this event; in truth, the specifics will never be more then a matter of speculation, except that a possible succession dispute had been dealt with.