伊達忍者 Date Ninja (Page 128–129) from the book Bessho Rekishi Dokuhon Vol. 72 – Shinobi no Mono 132-nin Data File. Written by 原遥平 Hara Yōhei (Historical Writer).
Masamune’s Direct Subordinate Ninjas: The Black-Clad “黒脛巾組 Kurohabaki-gumi”
▽ Those Wearing Black Leather Shin Guards

Regarding the ninjas of the 伊達家 Date-ke, they are mentioned in various sources. For example, a passage from “政宗記 Masamune-ki”:
“Then, in the military talks of 奥州 Ōshū, there are those called 草 Kusa, some lie in the grass, others rise from the grass, and some search the grass.”
In “北条五代記 Hōjō Godai Ki,” the name “Kusa” is also used, stating, “called ninjas.” The “Kusa” in Masamune-ki is undoubtedly synonymous.
Masamune-ki continues (summarized in colloquial language):

“Kusa reconnaissance or entering Kusa means infiltrating enemy territory at night. Depending on the enemy’s scale, besides the first Kusa, second or third Kusa wait behind, and the first Kusa sneaks near the enemy’s castle. Lying in Kusa means covertly observing enemy movements. Rising from Kusa means the first Kusa takes down those leaving the castle, regardless of number. If counterattacked, retreat without hesitation, fighting with the second or third Kusa. Also, annihilate enemy Kusa infiltrating the territory with full force. This is called searching the grass.”
Masamune-ki further notes, “Thus, Kusa is called 畫這 Gade.” Likely because, during the day, they crawl on the ground to observe the enemy. At night, “Kusa”; in the day, “Gade.” One can imagine those acting inconspicuously like roadside grass.

Also, in “仙台封内記 Sendai Hōnai-ki,” a komusō named 芭蕉 Bashō appears:
“During 貞山様 Teizan-sama’s era, there was a komusō named Bashō accompanying the Date. Bashō was granted 四辻 Yotsuji.”
This komusō Bashō is given the land of Yotsuji, and that Bashō was a ninja is known from: “In a world of constant warfare, Bashō was used as a secret envoy and spy.”
From these records, it’s easily inferred that the Date-ke had ninjas or ninja groups. In “伊達秘鑑 Date Hikan, (written by Iida Michitoki in 1770)” the shadow army clearly reveals its name: —黒脛巾組 Kurohabaki-gumi.
Kurohabaki refers to black leather shin guards (kyahan). The name derives from this group’s emblem, and the sight of those wearing black leather on their shins, moving stealthily day and night, is somewhat eerie.
Kurohabaki-gumi was a unit directly under 政宗公 Masamune-kō.

“Masamune-kō, with foresight, ordered 安部対馬重定 Abe Tushima Shigesada, lord of 倉夫郡鳥屋城 Kurahogun Toriya-jō, to select 50 skilled men, grant them support, and name them Kurohabaki-gumi. 柳原戸兵衛 Yanagihara Tohei and 世瀬蔵人 Sese Kurōdo were appointed leaders, with Abe Tushima directing them (note).”
Also, “老人伝聞記 Rōjin Denbun-ki” mentions Kurohabaki-gumi, naming, besides Abe Tushima, 清水澤兵衛 Shimizusawa Bei, 逸物惣右衛門 Itsutsumi Sōemon, 佐々木左近 Sasaki Sakon, 横山隼人 Yokoyama Hayato, and 気仙沼左近 Kesennuma Sakon. Date Hikan records:
“Placed in various locations, some disguised as merchants, yamabushi, or ascetics, and if skilled individuals emerged, they gathered secret information as opportunities allowed, reporting it promptly. Thus, Masamune heard matters quickly, but none outside knew.”
One of Kurohabaki-gumi’s tasks was intelligence gathering, as this description shows. Members disguised as merchants, yamabushi, or ascetics—professions free to travel the land. Faith was strong then, so religious figures were likely trusted. Or, yamabushi may have been part of Kurohabaki-gumi.
伊達忍者 Date Ninja (Page 128–129) from the book Bessho Rekishi Dokuhon Vol. 72 – Shinobi no Mono 132-nin Data File. Written by 原遥平 Hara Yōhei (Historical Writer).
I could not find much information about this book, who wrote it or the publisher. It looks like it was published as a history book/magazine published monthly.
Being the 72’nd book I guess it has been around for many years, the web site jinbutsu.co.jp is dead so I don’t know much about the publisher.

Published May 2001
228 pages
ISBN-10 : 4404027729
ISBN-13 : 978-4404027726