Lifespan: Tenshō 8 (1580) to 5/13 of Kanei 14 (1637)
Title: Junior Fifth Rank (Lower), Governor of Mimasaka
Lord: Toyotomi Hideyoshi → Toyotomi Hideyori → Tokugawa Ieyasu → Tokugawa Hidetada → Tokugawa Iemitsu
Domain: Head of Echigo-Zaōdō → Head of Shimotsuke-Mooka → Head of Shimotsuke-Karasuyama
Father: Hori Hidemasa
Mother: Daughter of Kitajima Ryōji
Siblings: Hideharu, Chikayoshi, Murakami Yoshitada, Kondō Masanari
Wife: [Formal] Yōbai-in (daughter of Asano Nagamasa)
Children: Chikamasa, Chikasato (?), Chikayasu, daughter (wife of Hino Sukeyoshi), Tsuruchiyo (adopted heir)
Hori Chikayoshi served as a daimyō during the Azuchi-Momoyama and early Edo periods. He was a first-generation member of the Hori family in the Shinano-Iida domain.
Chikayoshi was born as the second son of Hori Hidemasa. Chikayoshi, along with his father and older brother, Hori Hideharu, served Toyotomi Hideyoshi.
At the time of the Conquest of Odawara, he participated in his first battle at the age of eleven. After the death of his father, he governed a fief of 20,000 koku in Echizen Province. In 1591, he was conferred the title of Junior Fifth Rank (Lower) and Governor of Mimasaka and, from Hideyoshi, given the Hashiba family name and Toyotomi surname, in addition to the name of Hideie. Based on a letter he signed under the name of Hidenari addressed to Yamanaka Nagatoshi (who died in 1607), it was determined that he changed his name from Hideie to Hidenari prior to that year.
Thereafter, together with Hideharu, he was transferred to Echigo Province to manage a fief of 40,000 koku in Zaōdō in the Koshi District. He partitioned 10,000 koku from this fief for his chief retainer, Kondō Shigekatsu. Upon the death of Hideyoshi, he received a Sukezane sword (from a famous manufacturer during the mid-Kamakura period) as a keepsake.
In 1600, at the Battle of Sekigahara, Chikayoshi and Hideharu joined on the side of the Eastern Army. In the weeks prior to the main battle of Sekigahara that occurred on 9/15 of Keichō 5 (1600), Chikayoshi performed a key role in suppressing a revolt in Echigo launched by the Uesugi of Aizu in an event known as the Uprising by the Remnants of the Uesugi. Owing to his contributions, Chikayoshi received a letter of commendation from Tokugawa Ieyasu and Hidetada. The letter is addressed to Hashiba Mimasaka-no-kami dono so, around this time, he was still called by the Hashiba surname. After the war, Ieyasu officially recognized his rights to his territory.
Around 1602, he came into conflict with another member of the family, Hori Naomasa. Asserting reasons of illness, he went into seclusion at the residence of his deceased father in Fushimi near Kyōto. At this time, he assigned the headship of the clan to his adopted heir, Hori Tsuruchiyo. Accompanied by hereditary retainers, Chikayoshi then traveled via Kyōto and Ōsaka to Kishū (Kii Province) to visit the Asano family – the original home of his wife assigned by Ieyasu to govern a fief based in Wakayama in Kii. He consulted with his father-in-law, Asano Yukinaga, in regard to medical treatments, met Ieyasu in Sunpu, and followed orders to serve as a retainer of Hidetada. After working for four years, in 1611, he received a fief of 12,000 koku in Mooka in Shimotsuke Province and met with Hidetada in Edo. Meanwhile, during this period, the main branch of the Hori family was removed from its position, but Chikayoshi was not found to be complicit in the affairs that led to their demotion.
At the Siege of Ōsaka, he fought valiantly under the command of Doi Toshikatsu. Around this time, he abandoned the Hashiba family name and reverted to the Hori surname. He also changed his name from Hidenari to Yoshimasa. In 1618, he received an increase of 5,000 koku to his fief in Mino Province that had been taken from a reduction in the fief of his younger brother, Kondō Masanari. In 1627, he was granted Karasuyama Castle in Shimotsuke Province and held a fief of 25,000 koku in Karasuyama. His use of the name Chikayoshi is confirmed to have begun after he moved to Karasuyama.