Partially a joke and contest, this was created originally for 1st edition, as a variant of that edition's Monk. As part of my 5e "subclass as multiclassing" series, this is a monk/rogue.
Brotherhood of the Bond
The Brotherhood of the Bond is an order of spies in service to an island nation. Unlike many monastic orders, most are not trained from their youth to service, instead entering after a time in the military (or prison), and demonstrating exceptional talent, loyalty, and drive... maladjusted young men and women who give little thought to sacrificing others to protect Queen and Country. Building on their basic military or criminal backgrounds, the Brotherhood of the Bond introduces them to the arts of covertcy, as well as extensive training in unarmed and improvisational combat. Most members of the Brotherhood are LN, but LE and LG are not uncommon; those who are LE are prized for certain assignments due to their practicality, while the LG members frequently serve on security details for their aged queen and her family. While not a truly mystical order, the Brotherhood of the Bond holds that immortality comes through service to something beyond oneself; in their case, their nation. Many monks believe that exceptional agents will be reborn, again and again, always to rejoin the Bond and serve in Her Majesty's secret service.
The Brotherhood of the Bond does not have many of the traditional strictures placed upon monks, save discipline. As part of their work, they are frequently expected to drink, eat, and consort with all sorts of persons, in all sorts of situations. What must not waver, however, is discipline. They drink, but they avoid drunkeness. They eat such foods as are presented, but they avoid gorging themselves. They may gamble, take lovers, lie, cheat, and steal... but never from or to Her Majesty, her government, or their superiors. They may deal with money and other treasure, but keep little for themselves, returning or gifting most to the treasury as soon as they are able.
One's mastery is simply noted by one's level of experience, while one's assignment within the Brotherhood is noted by a complex code of one or two letters. This code is understood by all of the Bond, and so a simple three-character designation can tell a Brother or Sister much of what they need to know of another member.
The current head of the Brotherhood of the Bond is known to her underlings as M16, with M indicating one whose assignment is "Mastery", or leadership of other Brothers and Sisters. She is a formidable woman, even in her later years, and a frequent confidant of the Queen.
3rd level: Spectre
If not already proficient in them, the monk becomes proficient in one of the following skills: Stealth, Sleight of Hand, Investigation, Insight, Perception, Deception, or Persuasion. They also gain proficiency with one of the following, the disguise kit, forgery kit, or thieves tools.
As a reaction, upon failing a roll with one of these skills or tools, they may spend 1 ki point to roll the test again, and take the second result. This applies regardless of whether they are proficient with the skill or not.
6th level: On Her Majesty’s Secret Service
As covert agents, the monk must be able to pass in any number of professions, and use any number of tools. For 1 ki point, the monk may gain proficiency in a skill, tool, language, or weapon for 10 minutes. For 2 ki points, they may gain expertise in a skill or tool, with which they are already proficient, for 1 minute. These may be stacked, allowing the monk to become an instant expert with a skill or tool for 1 minute, with proficiency continuing for the full 10 minutes.
11th level: License to Kill
At 11th level, you may make a sudden strike against a target who you have surprised, or against whom you have advantage on attacks. Once per turn, against such a target, the monk does additional damage equal to their current ki points.
17th level: You Only Live Twice
At 17th level, the monk is able to transcend death in order to remain in service to Her Majesty and the Brotherhood. At the moment of death, and for up to three days thereafter, the monk may choose to reincarnate, as the spell. The new body will reappear in a safe place, up to five miles from the place of death or the current location of the mostly intact body.
In addition, members of the Brotherhood of this level may cast reincarnation on other members of the Brotherhood. This requires one hour and 5 ki points, but no verbal or material components, only constant contact with the corpse.
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