(Citing the Advanced Dungeons & Dragons, 1st Edition (AD&D1e) Player's Handbook (PHB) and Dungeon Master's Guide (DMG) as needed.)
(Monday's post is here, and Tuesday's is here, and yesterday's is here.)
Spies, Heists, & Assassinations
Thieves and Assassins have their own particular activities that either require downtime or are best handled in downtime. Monks, as they share certain skills with them, are also able to participate in these activities- to support or oppose. What the three activities have in common in the emphasis on stealth and deception, the cultivation and processing of raw data into useful information, and the execution of illegal (if not immortal) operations.
Spies
The hiring of spies as NPC Hirelings is addressed on DMG p. 34, which means that your man has to go through the process of locating and then securing the spy's services just like he would a Sage or other expert Hireling. That is a downtime commitment in itself, and then there is the time required to execute the job that the spy is hired to perform.
The DMG notes (ibid) that determining the success of a spy's job uses the Assassin Spying Table (p. 18), meaning that Assassin characters should be doing this on the regular when other activities do not compel their attention (such as Training or making Poisons). Be it done by your man or a Hireling, the duration of the mission is usually measured in days (for Simple and Difficult missions) but can go much longer (for Extraordinary missions).
The Dungeon Master (DM) has the discretion to allow other Classes to execute Spying missions, and I recommend that this discretion be exercised when the circumstances fit; allow a Thief to use the Spying Table to execute casing of a prospective heist target, a Ranger to scout the wilderness for threats or paths, etc. because such requests fit into the role that this Class plays and grants your man useful activities to pursue in downtime- activites that can set up more scenarios to play out at the table.
A Name Level Thief or Assassin will establish himself as a guildmaster with a gang of lesser Thieves/Assassins at his command. Becoming a spymaster as a revenue stream, and thus a major player in the Intelligence game, is going to become necessary to pursue the primary goal of attaining control of the local criminal underworld. Having control over such a spymaster is necessary for any would-be sovereign power; gaining power over the crown is necessary for a guildmaster that seeks to preserve his autonomy. This tension cannot be ignored or disdained, and it will emerge organically in play.
There is one other form of spying that needs to be addressed, and that is divination. All of the spell-casting classes possess multiple spells which allow either direct surveilance of a target or the ability to use another to do so, and that is before using magic to ask other parties questions--to interrogate--about a prospective target. Be it a Druid using Charm Person or Mammal to "make friends" who can "keep an ear open" for threats to his interests, a Magic-User using Clairvoyance and Clairaudience to eavesdrop on a target, a Cleric using Commune to discuss threats with his god, or an Illusionist hiding himself via Invisibility to observe someone. Each of these spells, and items that likewise facilitate spying, have their own PHB or DMG entries and I refer you to those for more details.
Heists
The Spying Table and the array of missions it addresses permits the spy to steal from the target. (p. 18) This includes pulling off long-term operations, which are classified as Extraordinary and thus have a low chance to succeed, but for practical purposes the point of doing this is for players to set up future action against prospective targets by getting passwords, keys, maps, etc. beforehand to facilitate their personal intervention to execute the heist.
As above, this use of Spies and Spying may be done by other Classes as the DM's discretion; a Ranger should be allowed to use the Spying Table to trail a warband of goblinoids and report back their movements, for example.
This particular rule and mechanic exists to allow the players to advance their own campaign plans away from the table in the form of identifying targets and gathering useful intelligence and aids against them prior to direct action. As their resources grow that can--and should--including dispatching hired hands or useful followers to do even full-on heists against targets that they cannot handle themselves.
Some may object to this possibility. Look again at the Spying Table; the odds of such complex and long-duration operations are low, and the consequences high, which will be sufficient to keep this downtime activity used for more standard actions of casing a target and getting some access aids. Furthermore, the consequences for failure include the possibility of the employing player being revealed to the target. The player needs to weigh risk versus reward, and some players are bad at math; let them fail and suffer for it. That is far more effective at curbing potential abuse than anything else.
But there is something higher-risk than theft, which is left for last.
Assassinations
This is the core function of the Assassin Class, and it is for this class that the Assassination Table exists. Assassin characters in particular want to do this because it awards Experience Points (PHB. 29)
The hiring of Assassins is a job in itself, as they are considered Expert Hirelings, and the duration of the mission is just Spying with an extra step so you can just use the Spying Mission guides. (time in days, varying by difficulty)
As with planning heists, an Assassin planning an assassination will employ Spying to gather intelligence regarding the target in order to stack the odds in his favor. (DMG p. 75).
Before an Assassin gets locked down on a time commitment to the assassination mission he will be forced to decide upon locking down on Spying Missions to case the target, or doing something else (such as Poison creation) while managing the NPC Spy doing that work for him. The Assassin has incentive to be meticulous regardless of all else in order to maximize success. One die roll can mean the difference between a kill and getting killed (or worse).
Moreso than any other Class, the Assassin has reason to become an expert on these mechanics and procedures because this directly and immediately affects the core function (and therefore activity) of the Class. This also means that the Assassin has good reason to maintain good relations to parties that he can rely upon to substitute for himself, or to do what he cannot- even the Chaotic Evil Half-Orc.
Commentary
This is the sort of thing that characters should be doing when they are not otherwise occupied. If they are not hiring and dispatching others to spy for them, then they should do it themselves. Rangers tracking giant-class monsters, Thieves and Assassins scouting targets, Monks surveiling areas under their control, spell-casters seeking out threats to themselves of their Patron's interests, Fighters (and everyone, really) doing counter-surveilance to deal with enemy spies and scouts, etc. to prevent hostile parties from getting surprise on them- this is also part of the game and not to be disdained.
This only grows in importance as characters rise up and attain Name Level, entering the Domain Game fully as Patrons unto themselves.
Which means that, put into practice, the downtime play of a campaign is going to be as relevant to overall campaign play at all levels as play at the table. Tomorrow, to wrap up the week, I'll show you a likely scenario where all of this stuff comes together.
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