Uesugi Kagekatsu served as a daimyō from the Sengoku to early Edo periods.  In the Edo period, Kagekatsu served as the first lord of the Yonezawa domain in Dewa Province and as the seventeenth head of the Yamanouchi-Uesugi family (the main branch of the Uesugi clan).

Kagekatsu was a member of the gotairō, or Council of Five Elders, a group of powerful daimyō formed to manage the affairs of the Toyotomi administration prior to the death of Toyotomi Hideyoshi.

Kagekatsu originated from the Ueda-Nagao family and was first known as Nagao Akikage.  He was adopted by his uncle, Uesugi Kenshin (from the same family), and changed his name to Uesugi Kagekatsu.  In 1578, the death of Kenshin without a natural heir gave rise to a succession struggle in the Uesugi family known as the Otate Conflict.  Kagekatsu prevailed in the conflict, becoming the successor to Kenshin as the head of the Uesugi family.

Kagekatsu served Toyotomi Hideyoshi, and, as a member of the Council of Five Elders, held territory of 1,200,000 koku in the Aizu domain.  The death of Hideyoshi in 1598 ushered in a period of instability as senior retainers vied for power.  In 1600, Tokugawa Ieyasu led an expedition to subdue Kagekatsu known as the Conquest of Aizu, marking the prelude to the Battle of Sekigahara during which Kagekatsu joined the Western Army led by Ishida Mitsunari and was defeated.  After the war, Ieyasu permitted the survival of the Uesugi family but the Yonezawa domain was reduced to a fief of 300,000 koku.

Youth

On 11/27 of Kōji 1 (1555), Kagekatsu was born as the second son of Nagao Masakage, the head of the Ueda-Nagao family below Sakado Castle in the Ueda manor of the Uonuma District of Echigo Province.  His childhood name was Umatsu and, later, Kiheiji Akikage.  His mother was Sentōin, the older sister of a different mother of Nagao Kagetora (later Uesugi Kenshin).

Kagekatsu’s maternal grandmother (Sentōin’s mother) was the daughter of Jōjō-Uesugi Danjō-Shōhitsu.  Kagekatsu’s paternal great-grandmother (the mother of Ueda-Nagao Fusanaga) was also a daughter of the Jōjō-Uesugi family.  Therefore, Kagekatsu carried the bloodline of the original Uesugi clan (the Jōjō-Uesugi serving as military governors of Echigo) from both of his parents.

Kagekatsu’s eldest brother died early so he became the designated heir but, in 1564, after the drowning of his father, Nagao Masakage, he entered Kasugayama Castle and was adopted by his uncle, Uesugi Kenshin.  Kenshin and Kagekatsu represented two generations of the Nagao family who inherited the headship of the Uesugi family.  The lineage of his maternal grandfather, Nagao Tamekage, served, from the era of his great-grandfather, Nagao Yorikage, as deputy military governors of Echigo.  In the era of Tamekage, the family backed Uesugi Sadazane and forced Uesugi Fusayoshi to take his own life.  Thereafter, the relationship between Tamekage and Sadazane deteriorated but his grandfather, Nagao Fusanaga (the head of the Ueda-Nagao clan), allied with Sadazane.

In 1566, Kagekatsu had his first experience in battle during the deployment by Kenshin to the Kantō.  Kagekatsu then led the Ueda group and performed important roles in Kenshin’s administration such as mediation with a commander in Etchū named Shiin Yasutane and designation of the military service of Yoshie Sukekata, a hatamoto of Kenshin.

In 1575, he changed his name from Nagao Akikage to Uesugi Kagekatsu (or, according to one theory, Nagao Kagekatsu).  Keshin also transferred to him the official title of Danjō-shōhitsu, or Deputy Inspector.  That same year, according to the military service records of the Uesugi family, he was responsible for the service of 375 soldiers and is listed as a leader among members of the Uesugi family and referred to as Onchūjōsama while Kenshin is referred to as Omijōsama.

Succession struggle in the Uesugi family

After the death of Kenshin on 3/13 of Tenshō 6 (1578), a succession struggle erupted between Kagekatsu and Uesugi Kagetora who was adopted by Kenshin after being tendered as a hostage from the Gohōjō.  This event is known as the Otate Conflict.  This conflict was the result of a complex set of circumstances including the fact that Kenshin suddenly died without designating a successor as well as power struggles occurring over generations among branches of the Nagao family of Echigo Province.

On 3/24, by quickly occupying the main citadel of Kasuga Castle and storage of assets, the supporters of Kagekatsu were in an advantageous position vis-à-vis Kagetora who holed-up in the Otate, the residence of Uesugi Norimasa below Kasuga Castle.

In the sixth month, based on an alliance between the Takeda of Kai Province and the Gohōjō of Sagami Province, Takeda Katsuyori deployed to the provincial border of Shinano and Echigo in an effort to mediate between Kagekatsu and Kagetora, placing Kagekatsu in a precarious situation.  On the condition that he allocate eastern Kōzuke as well as transfer gold, Kagekatsu achieved peace with the Takeda clan and obtained their backing, changing the posture of the war.  Furthermore, he became engaged to Kikuhime, a daughter of Takeda Shingen (Katsuyori’s younger sister of a different mother) and, in the ninth month of the following year, received her as his formal wife, thereby forming a political alliance between the Takeda and the Uesugi clans.  After the Tokugawa clan of Mikawa Province invaded Suruga Province, Katsuyori withdrew from Echigo that same year.

In 1579, Seienin, the formal wife of Kagetora and daughter of Nagao Masakage, did not accept a warning to surrender from Kagakatsu and took her own life.

In the third month of 1579, Uesugi Norimasa (Kagekatsu’s adoptive grandfather) proposed a settlement but, along with Dōmanmaru (Kagetora’s son) was killed by some people so, in the midst of deteriorating circumstances, Kagetora killed himself.

In 1580, after Kagekatsu ingratiated himself with gōzoku, or wealthy families, in Echigo, both in form and in substance, he succeeded Kenshin as the next head of the Uesugi family.  In the aftermath of the war, Kagekatsu limited rewards to the gōzoku with whom he allied and instead promoted retainers of the Ueda-Nagao lineage to important positions.  He purged the kokujin, or provincial landowners, against whom he and Kenshin had fought including those formerly aligned with Kagetora as well as those who sought independence.  Consequently, he built a clan organization that was completely controlled by members of the Ueda-Nagao family and their retainers.

Battles against the Oda family

In 1576, the Uesugi clan under Kenshin reconciled with the Hongan Temple, making them opponents of the Oda clan.  In 1581, in the midst of the chaos caused by the Otate Conflict, owing to a lack of rewards for his support, Shibata Shigeie from northern Echigo colluded with Oda Nobunaga while an army of 40,000 soldiers led by Shibata Katsuie invaded as far as Etchū Province.  In the third month of 1582, during the Conquest of Kōshū, the Takeda were extinguished by the Oda army, nullifying their promise to deploy to Etchū.  Having lost the backing of the Takeda, the Uesugi confronted the prospect of annihilation.

After the Siege of Uozu Castle from the third to sixth months of 1582, the Oda seized control over most of Etchū.  At Tenjinyama Castle, Kagekatsu desperately prepared for an assault by a menacing Oda army.  Just before the fall of Uozu Castle, Kagekatsu sent a letter to encourage Shibata Katsuie and the garrison defending the castle.  In this letter, Kagekatsu praised the loyalty and contributions of each defender of the castle, but, in the end, the defenders died during the fall of the castle.  In the fifth month, in a letter to Satake Yoshishige, Kagekatsu noted: “We were born in a good era.  From our province of Echigo, we fought against those from over sixty provinces and, even if annihilated, will be remembered for posterity.”

Kagekatsu was prepared for an honorable defeat in a final showdown against Oda Nobunaga.  Then, on 6/2 of Tenshō 10 (1582), Nobunaga died in a coup d’ètat launched by Akechi Mitsuhide in an event known as the Honnō Temple Incident.  The northern conquest of the Oda army stalled and the Uesugi family spared.  In addition to the hardship posed by the invasion by the Oda, in the chaotic aftermath of the Otate Conflict, the Uesugi witnessed a loss of authority over their territory.  The significant power of the Uesugi clan that Kenshin achieved in one generation dramatically declined.  Meanwhile, owing to his resentment toward Kagekatsu for his preference for members of the Ueda group, Shibata Katsuie revolted, triggering the Battle of Hōjōbashi.  Prominent commanders including Sugana Tajima-no-kami, Suibara Mitsuie, and Ueno Kyūbei were killed in action, while Yasuda Yoshimoto incurred serious injuries.  Kagekatsu himself was nearly corned and suffered an ignominious defeat.

Service to the Toyotomi administration

Upon receiving news of the coup d’ètat, the Oda army that had marched on a northern conquest returned to the Oda territory, providing an opening for Suda Mitsuchika to recapture Uozu Castle.  As kokujin, or provincial landowners, in Shinano revolted against Mori Nagayoshi as the governor of Kawanakajima, the Uesugi army acted in coordination by launching an invasion of northern Shinano.  At the same time, the Uesugi fought against Hōjō Ujinao over territory in Shinano after Ujinao expelled Takigawa Kazumasu from Kōzuke Province.  The two parties settled on the condition that the four districts of northern Shinano be allocated to the Uesugi.  This is known as the Tenshō-Jingo Conflict.

Later, Kagekatsu fostered relations with Hashiba Hideyoshi (later known as Toyotomi Hideyoshi) who rose to prominence in the Oda administration.  In 1583, at the Battle of Shizugatake, Kagekatsu was ordered by Hideyoshi to invade Etchū.  This, however, led to a stare down against Sassa Narimasa (who sided with Shibata Katsuie) so he did not move.  Meanwhile, that same year, Suda Mitsuchika withdrew from Uozu Castle to Kaizu Castle in Shinano.

In 1584, at the Battle of Komaki-Nagakute, Kagekatsu supported Hideyoshi and forcibly recovered Miyazaki Castle from a retainer of the Sassa named Niwa Gonpei.

In 1585, Kagekatsu allied with Hideyoshi for the Toyama Campaign and contained Sassa Narimasa.

That same year, he temporarily subordinated Sanada Masayuki who controlled the Chiisagata District in Shinano and the Agatsuma (Iwabitsu) and Tone (Numata) districts in Kōzuke.

In the sixth month of 1586, he went to Kyōto, met Hideyoshi, and tendered his adopted son, Hatakeyama Yoshizane (who, at the time, had the Uesugi surname) and pledged obedience to Hideyoshi to preserve his life.  On this occasion, he abandoned territory in Etchū held to the west of Tenjinyama and Miyazaki in addition to the Agatsuma and Tone districts of Kōzuke and the Chiisagata District of Shinano, enabling the Sanada to operate independently as a daimyō family under the Toyotomi.  In exchange, he was permitted to eliminate the Shibata clan in Echigo and take over the Shōnai area of Dewa Province.  At this time, Kagekatsu met Emperor Ōgimachi and was invested with the title of Major General of Imperial Guardsman of the Left Division.

In 1587, with the backing and support of Hideyoshi, and after many years of conflict, Kagekatsu killed Shibata Shigeie during a revolt and nearly reunified Echigo (only Tsugawa Castle, until the exchange of Shinkawa and east Kanbara in 1595, was held by the Date and, later, the Gamō and Toyotomi).  Notwithstanding an order issued by the Toyotomi administration later that year to prohibit territorial disputes between daimyō, the Uesugi cut-off Sado and Dewa provinces.

In 1588, Honjō Shigenaga and Honjō Yoshikatsu (father and son) invaded the Shōnai and, at the Battle of Jūgorigahara, Kagekatsu defeated the Mogami army and took control of three districts in the Shōnai area.  Later that year, Kagekatsu traveled again to Kyōto and was conferred the Toyotomi and Hashiba surnames and, on 6/15 of Tenshō 16 (1588), the title of Third Rank (Lower) and Councilor.

In 1589, Kagekatsu subdued the Honma clan of Sado and pacified the province.

In 1590, during the Conquest of Odawara led by Hideyoshi, Kagekatsu deployed with Yamaura Kagekuni in the vanguard and, together with Maeda Toshiie and Sanada Masayuki, captured several castles defended by the Hōjō in Kōzuke and Musashi.

In 1592, upon the commencement of deployments for the Bunroku Campaign, Kagekatsu led 5,000 men to be stationed at Nagaoya in Hizen Province.  From 6/6 to 9/8 of Bunroku 2 (1593), while serving as a representative of Hideyoshi, Kagekatsu, along with others including Takanashi Yoshichika, crossed to the Korean Peninsula.  He then constructed a castle in 熊川 to serve as a base for the Japanese army on the front lines of the battle in Korea.

In 1594, Kagekatsu was conferred the title of Provisional Vice-Councilor of State and called the Vice-Councilor of State of Echigo.

In the first month of 1595, he was delegated by Hideyoshi the management of gold and silver mines in Echigo and Sado provinces.  The income from mining operations in the territory of the Uesugi exceeded that of other lords.  According to records, the taxes from gold mining in Echigo were 1,124 mai, 4 ryō, 1 monme, 1 fun, and 2 rin, accounting for 33% of the income from mining among all daimyō, while the taxes from silver mining in Echigo were 2,021 mai, 7 ryō, 3 monme, 3 fun, and 3 rin, accounting for 59% of the income from mining among all daimyō.

In the second month, after the outbreak of the Gamō Disturbance, upon orders of Hideyoshi, he sent the Fujita clan to Tsugawa Castle in east Kanbara while Shinkawa became the territory of the Maeda.  He then had members of the Etchū group including Doi Masashige vacate and transfer Tenjinyama and Miyazaki castles to Aoyama Yoshitsugu, a retainer of Maeda Toshinaga.  As a result, his territory included the provinces of Echigo and Sado, in addition to the four districts of Kawanakajima in Shinano and the three districts of Shōnai in Dewa, for a total of 910,000 koku.  Furthermore, he held over 100,000 koku in the Kyōto area.

From the sixth month, six powerful daimyō including Kagekatsu were appointed as tairō, or chief ministers, of the Toyotomi administration.  After the death of Kobayakawa Takakage, this group was called the gotairō, or Council of Five Elders.

In 1598, upon orders of Hideyoshi, Kagekatsu received an increase of his fief to 1,200,000 koku and thereafter was called the Vice-Councilor of Aizu.  With respect to his former territory, he was permitted to continue to govern only Sado Province in addition to a small portion of Echigo acquired during the Gamō Disturbance (east Kanbara) and the Shōnai area of Dewa.  The remainder was comprised of territories that were controlled by the Date including the Okitama area of Dewa, the Date, Shinobu, and Katta districts of Mutsu Province, and the Aizu area conquered by Date Masamune.  These were remote mountainous areas connected only via ridgelines.  There was a persistent risk of clashes with Masamune and Mogami Yoshiaki whose territories ran along the northern border.  After the Gamō clan witnessed a reduction in their fief to 120,000 koku in Utsunomiya, Kagekatsu was given important responsibilities to monitor and contain Tokugawa Ieyasu along with various daimyō in the Tōhoku region.  As a result, he could not avoid conflict with Ieyasu.  He positioned his chief retainer, Naoe Kanetsugu, in the vital location of Yonezawa Castle and, on the front lines to oppose the Date clan, had Amakasu Kagetsugu of Shiraishi Castle, Honjō Shigenaga of Fukushima Castle, Suda Nagayoshi of Yanagawa Castle, and Shida Yoshihide of the Tōsenji Castle, serve as commanders.

Conquest of Aizu

After the death of Hideyoshi in the eighth month of 1598, owing to friendly relations that his chief retainer, Naoe Kanetsugu, maintained with Ishida Mitsunari, one of the gobugyō, or Five Commissioners, of the Toyotomi administration, Kagekatsu came into conflict with Tokugawa Ieyasu.  In the ninth month, he went to Kyōto for the memorial service for Hideyoshi.

In the second month of 1600, Kagekatsu ordered that several castles in his territory be repaired by the summer.  In the third month, he determined that Tsuruga Castle would be cramped in the future so he ordered the construction of Kōzashi Castle near the center of the Aizu Basin.  In the fourth month, Kagekatsu received orders from Ieyasu summoning him to Kyōto to explain the renovations to castles in his territory, but Kagekatsu refused.  The summons appeared to be a ploy to eliminate Kagekatsu.  In this case, an inflammatory response from Kanetsugu instigated the Conquest of Aizu by Ieyasu.  This communication is known as Naoe’s Missive.  Ieyasu led an army of 55,000 soldiers on an expedition to subdue Kagekatsu.  Meanwhile, Kagekatsu ordered the construction of Kōzashi Castle at full speed, but, in the sixth month, the work was suspended to prepare for Ieyasu’s army.

In the seventh month, while Ieyasu was en route to Aizu, an urgent message sent by Torii Mototada (a retainer of Ieyasu based at Fushimi in Kyōto) arrived, whereupon Ieyasu learned that Ishida Mitsunari had gathered forces in Ōsaka with the intention of toppling Ieyasu.  Ieyasu then immediately summoned his generals for a war council known as the Oyama Deliberation.  The meeting was held in the Suga Shrine on the southern grounds of Oyama Castle.  The key options on the table included: (i) continue with the plan to attack the Uesugi, (ii) change course by turning west to challenge Mitsunari, or (iii) ally with Mitsunari.  Most of the generals serving Ieyasu came from families that had been retainers of the Toyotomi for generations, with wives and children in Ōsaka.  The decision whether to proceed as planned or return to Ōsaka represented a crucial turning point for Ieyasu’s future.  After a spirited deliberation, Ieyasu made a final decision for the Eastern Army to turn west to attack Mitsunari in Ōsaka.

Once the Tokugawa army turned back to head west, Kagekatsu deployed from Aizu and clashed against Date Masamune and Mogami Yoshiaki at the Battle of Keichō Dewa.  On 9/15 of the ninth month, at the Battle of Sekigahara, Mitsunari and the Western Army were defeated so, in the twelfth month, Kagekatsu was compelled to surrender to Ieyasu.  The resistance by the Uesugi family reflected the inability of a powerful daimyō family to overcome the propensity to govern their territory and residents in a centralized manner with a focus on managing their new territory of Aizu.  Underestimating the changes to the political situation and neglecting the new systems of governance under Ieyasu led to errors with respect to their policy priorities, triggering the Conquest of Aizu by Ieyasu.

Early in the second month of 1601, Ieyasu, through the mediation of Yūki Hideyasu, via a priest named Saishō Jōtai of the Hōkō Temple, reached out to Kanetsugu, urging him to have Kagekatsu visit Kyōto to apologize.  After Kagekatsu and Kanetsugu came to the capital and apologized to Ieyasu, the Uesugi clan was formally permitted to continue to exist.  In 1595, Kagekatsu’s wife (Kikuhime) and Kanetsugu’s wife (Osen-no-kata) who had resided in Fushimi as witnesses (of the loyalty of their husbands) to the Toyotomi administration remained in the Fushimi residence as witnesses for their husbands to the Tokugawa.

During this period, prior to a determination, rumors abounded regarding the punishment to be meted out to Kagekatsu.  Kamata Masachika, a retainer of the Shimazu clan, sent home a letter stating that “Ieyasu will have the daughter of Naoe Kanetsugu wed Takeda Nobuyoshi and have him inherit the Uesugi clan with a fief of 1,000,000 koku, and Kagekatsu will receive a retirement income but the amount granted and where he will reside have not been decided.  Meanwhile, Date Masamune communicated via Imai Sōkun to Ieyasu that Kagekatsu should promptly be enfeoffed in Aizu.  In fact, the conferral of honors to Nobuyoshi and Gamō Hideyuki (the prior landlord of Aizu who in the end was enfeoffed in Aizu) had not as of this time been determined.

Although he avoided removal from his position, in the eighth month, Kagekatsu’s punishment was formally decided during the assignment of daimyō in the Ouu region.  His fief was reduced to 300,000 koku in Yonezawa in Dewa comprised of the Okitama, Shinobu, and Date districts.  The Uesugi family, in the course of one generation, devolved from their status as a major daimyō family controlling Echigo, Shinano, and several provinces in Hokuriku to a common daimyō holding only one-half of Dewa and two districts in Mutsu Province (with an assessed yield of 300,000 koku and actual yield of 510,000 koku).

Service as the lord of the Yonezawa domain

Kakekatsu renovated and expanded Yonezawa Castle, making it his residence.  Meanwhile, he continued to place senior retainers in auxiliary castles, including Fukushima Castle, in Mutsu.  After his transfer, in the early days of the Edo period, he made efforts to establish the administration of the Yonezawa domain.

On 2/21 of Keichō 8 (1603), the Edo bakufu granted him a residence for visiting representatives of the domain to stay in Sakurada in Edo.  He also continued to own daimyō residences in the environs of Kyōto including in Fushimi and Ōsaka.

In the second month of 1604, Kikuhime died and, in the fifth month, a consort gave birth to a son named Tamamaru (later Uesugi Sadakatsu).

In the fourth month of 1605, he attended a ceremony to proclaim Tokugawa Hidetada as the second shōgun of the Edo bakufu.

In the second month of 1609, his mother, Sentōin, died.

In the fourth month of 1610, he met Tokugawa Ieyasu in Sunpu and, toward the end of the year, Tokugawa Hidetada paid a visit to the residence for the Yonezawa domain in Sakurada in Edo.

In the first month of 1614, when Matsudaira Tadateru constructed Takada Castle in Echigo as his base, Kagekatsu engaged in infrastructure development under the direction of Date Masamune according to the policies of the Edo bakufu.

In the tenth month of 1614, the Toyotomi family refused to submit to the Edo bakufu led by the Tokugawa family, triggering the Winter Campaign of the Siege of Ōsaka.  On this occasion, Kagekatsu submitted a written pledge of obedience to the Tokugawa and, together with Naoe Kanetsugu, deployed.  On 10/12 of Keichō 19 (1614), Kagekatsu met Ieyasu at Nijō Castle and, on 10/25, he made significant contributions at the Battle of Shigino.  He entered the new year while in Ōsaka and, in the second month, returned for a while to Yonezawa.

In the fourth month of 1615, the Toyotomi refused a demand from the Edo bakufu to depart from Ōsaka so he deployed again.  During the Summer Campaign of the Siege of Ōsaka, Kagekatsu was responsible for security in Kyōto and established a base on Mount Hachiman.

In the fifth month of the same year, Ōsaka Castle fell and Kagekatsu returned to Yonezawa.

In the fourth month of 1619, he accompanied Tokugawa Hidetada on a trip to Kyōto.  At the end of this year, his chief retainer, Naoe Kanetsugu, died.

In the ninth month of 1621, Kagekatsu, along with Date Masamune and Satake Yoshinobu, attended a banquet hosted by Tokugawa Hidetada.

In the ninth month of 1622, upon the removal of Mogami Yoshitoshi (the grandson of Mogami Yoshiaki), the lord of the Yamagata domain in Dewa, Kagekatsu assisted to take over the Yoshitoshi’s residence at Yamagata Castle.

In the second month of 1623, his illegitimate son, 千徳, met Tokugawa Hidetada and adopted the name of Sadakatsu.

On 3/20 of Genna 9 (1623), Kagekatsu died at Yonezawa Castle.  He was sixty-nine years old.  Two retainers, Takano Magobei (Director of the Palace Table) and an assistant, Nakano Jinsuke, martyred themselves and were buried along with Kagekatsu at the Hōon Temple in Yonezawa.

Kagekatsu was succeeded by Sadakatsu.  Although there were adjustments to the size of the fief, the Uesugi family of the Yonezawa domain continued until the end of the Edo period.

Character and anecdotes

There is a legend that Kagekatsu laughed only one time in his life.  On one occasion, a pet monkey took a hat that was set down near Kagekatsu and climbed-up a tree.  After sitting on a branch, the monkey put on the hat and then bowed while Kagekatsu was preparing to sit down.  At that moment, Kagekatsu laughed without a thought.

When Kagekatsu came to Kyōto upon invitation of Hideyoshi, he was accompanied by several hundred people.  The soldiers and commanders of the Uesugi clan displayed a sense of dignity, marching in a solemn manner without idle talk.  The only sounds heard were those of the men and horses marching down the road.

While crossing the Fuji River in a boat, there were too many soldiers on board so it began to sink.  Kagekatsu became upset and grabbed a pole while all of the other passengers jumped into the river and swam to the other shore.  The boat in which Kagekatsu road then safely landed.

Kagekatsu had a strong interest in swords and the knowledge to assess their value.  He made a record of the thirty-five swords that he particularly favored and included in the list are many regarded as national treasures or important cultural assets.

On one occasion, Toyotomi Hideyoshi held a banquet (either in Fushimi or at Ōsaka Castle) to which he invited numerous daimyō.  Among the attendees was a bushō named Maeda Keijirō (Toshimasu).  At the height of the festivities, Keijirō, from the lowest seat, put on an ape mask, covered his head with a cloth, and waved a folding fan while performing an animated dance.  He then sat alongside some of the daimyō and imitated the behavior of a monkey.  Understanding that this was entertainment, the daimyō present did not criticize him or become mad.  When, however, Keijirō approached Kagekatsu, he avoided sitting alongside him.  Asked why, Keijirō responded “When I came in front of him, he appeared solemn and dignified, so I could not sit next to him.”  He further said, “Even if the world is huge, there is no one other than Kagekatsu whom I would truly depend upon as my lord.”  This act of respect shown by Keijirō showed the trust he placed in Kagekatsu as a man of true honor.

Kagekatsu had only one natural child, an illegitimate son.  According to a war chronicle from the Ouu region, he abhorred women and had a poor relationship with his formal wife, Kikuhime.  He preferred pederasty and kept handsome young men around.  To ensure an heir for the clan, Naoe Kanetsugu dressed-up a prostitute (the daughter of a retainer of Ōtani Gyōbu (Yoshitsugu) and a consort from the Yotsutsuji clan) to appear as a young man, matched her with Kagekatsu, and she later bore Sadakatsu.  Upon learning of this act, Kikuhime became enraged so the harlot who bore Sadakatsu took her own life while, many years later, a resentful Sadakatsu sought to kill Kanetsugu himself.  This story, however, conflicts with other accounts and therefore is of questionable authenticity.  Meanwhile, in the eighth month of 1612, Kagekatsu issued an order to prohibit acts of pederasty, so there is a theory that this practice was not allowed in the family.

After the move to Yonezawa, and despite a significant reduction in the size of the fief, the family did not disperse and none of the existing retainers departed so the clan faced difficult financial conditions.

The town of Kagekatsu in the Fushimi ward of the city of Kyōto has its origins as the location of the daimyō residence of Kagekatsu in the former capital.

Kagekatsu was tolerant of Christianity.  According to a report from a missionary in Aizu-Wakamatsu to the head of the Jesuits, when the Edo bakufu issued a prohibition order and he was ordered to enforce the policies in his territory, he responded that there were no Christians in his domain and protected them.  Pedro Morejon, a Jesuit missionary from Spain noted in regard to Kagekatsu: “He was a heretic among heretics” and did not show goodwill toward Christians but did not want to lose capable retainers with whom he had shared many experiences, good and bad, over many years.  In 1620, at the beginning of the Sendai domain, numerous domains in the Tōhoku engaged in acts of suppression against Christians.  Until the demise of Kagekatsu in the third month of 1623, official bulletin boards prohibiting Christians were posted in the Yonezawa domain in accordance with the orders of the bakufu, but there are no records of enforcement actions against Christians or the suppression of Christians in the territory.

There is a theory that two letters from Kenshin concerning the conferral upon Kagekatsu of the title of Deputy Inspector have the same handwriting as Kagekatsu and thus were fabricated by Kagekatsu for his own purposes.  However, a letter from Uesugi Kagetora to Ashina Moriuji refers to this title in relation to Kagekatsu.  This is evidence that a rival of Kagekatsu referred to him with this title in correspondence to a daimyō from another province, thereby substantiating that Kagekatsu did receive this title.