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With Burn Notice recently and my dad giving me Foresyth novels, I have grown a love for espionage-based novels. Up to the point that I have gained interest in it and want to write a stories involving spies and espionage.

As usual, I want to avoid the bullshit. I know that (at least, the older) James Bond movies are a poor source of information. I know that a spy fails when he has to start lugging bullets into his mark. I know that torture is a bad way to get information out of someone. I know that they usually impersonate someone in order to acquire secrets. I also know that their main interest is usually secrets and not assassinations or sabotage.

I believe that Burn Notice does a good, if at least attempted to be honest, job at showing at showing what's it like to be a spy. They show the bad and the boring as much as they show the cool and good.

Like usually, I sadly can't afford to buy books online. Well, at least not right now, especially with Christmas closing in just next week and I like to settle the whole gift thing before the madness starts. I doubt that there is that much useful stuff in the local libraries, besides there is still a cast on my foot and the library well within is in a no-car area.

So, can anyone give me good sources/ links / etc about the subject? Or even just personal thoughts, musing and ideas? Hell, a spy dictionary would be very helpful!

Even a "what to and what not to do" list would be very helpful.

What I'd like to know, is:
- how does someone become a spy?
- what training or background makes someone an ideal candidate?
- how much does combat training and performance matter?
- what happens when the spy retires, either on his own volition or against it?
- how does a burn notice work exactly? Is the portrayal in Burn Notice (the show) accurate or more of an exceptional case?
- what training do spies receive?
- how and when does a spy normally retire?
- what quirks does a spy normally acquire?

I detect a minor logical flaw in your argument. Is anyone genuinely qualified to speak authoritatively on these matters actually likely to openly admit it?

Seriously, everything I know about the espionage business I got from spy novels. And a memoir or three and a history here and there.

MIs 5 and 6 do run recruitment ads; it could be that simple. Co-option is another method- somebody you know thinks you might make a good intelligence officer, and mentions that to someone they know who the middle man thinks they might know an intelligence officer, at one or two removes.

Could be a direct approach; I think it was Max Hastings who in his memoirs describes, carefully, an incident in which an old acquaintance of his asked him to do a little work for the SIS on the grounds that he was nearly doing it anyway, just keep his eyes and ears open a little wider. He claims to have said no.

Incidentally, according to another journalist- John Simpson- who interviewed the then head, MI6 rather approve of James Bond. Competely unlike the real job of course, but apparently the associated cool factor helps their recruiting considerably.

Which are appropriate comments, because a lot of the human- intelligence side of spying is basically journalism, albeit played for high stakes. Also, a lot of the work is not done by the intelligence officers themselves, but by the local contacts they have recruited, by whatever means they thought would work; blackmail, bribery, appeal to conscience, simple friendship, whichever.

Intelligence officers are part of the civil service, covered by the Official Secrets Act, are expected to retire at the normal age and recieve whatever the usual pension for that grade is. The intelligence services are government agencies, and unfortunately that also means government paperwork.

Analysis is a whole separate issue. The KGB, towards the end, was reputed to be extremely good at attracting information, but crippled in terms of how it could present it- it could not report anything the Party did not want to hear. The CIA and MI6 may have had something of the same problems- Iraqi WMD?

Basically, I would describe the makeup of a plausible-fictional intelligence officer as three parts journalist, two parts personnel manager, one part actor and four parts file clerk. There's hardly any kaboom involved at all. Add a small side order of psychologist and diplomat, and there you go.

If you haven't watched La Femme Nikita yet - watch it.

Can't speak for its accuracy, but it's great on atmosphere.

Old or older books are fine by me too.

The guy I have in mind is a post-Stalin, Cold Warrior and the book is set about 6-7 years after the fall of the Berlin War.

I detect a minor logical flaw in your argument. Is anyone genuinely qualified to speak authoritatively on these matters actually likely to openly admit it?

I don't want classified stuff (for more reasons that just accessibility obviously). I am sure that there are spies out there that worked with cases old enough that they can talk about it and give you a general idea about more modern operations.

What I am also interested in, is espionage techniques as my character is likely to use these. Old tricks would be especially neat.

- how does someone become a spy?

You send a CV. It really is that simple: you send a CV and wait. The intelligence agency will then interview you, like for any other job - it's just that requirements are more stringent. Before you get to even look at anything secret, you will have to pass various tests and psychological evaluations...then you are sent to school. Every country maintains one, the students usually live on the premises and good luck getting in if you're not invited.

There the potential officers (not agents, officers) learn all the stuff they need, like languages, fieldcraft, procedures, etc.

- what training or background makes someone an ideal candidate?

AFAIK, any degree related to psychology, military backgrounds are looked at favorably, cops are good candidates, too. Women are preferred slightly over men, incidentally. Supposedly, they pay more attention to details.

- how much does combat training and performance matter?

Not much. A field officer is mostly expected to work people, not fight them. There are usually designated people for things like abductions, who do it in stead of more valuable officer.

- what happens when the spy retires, either on his own volition or against it?

AFAIK, they sign an NDA and simply retire. Plenty of former spies wrote books about their work after their NDAs expired.

- what training do spies receive?

Languages, fieldcraft, negotiation, procedure, culture, physical training,drinking alcohol (priceless skill in the East ) are some I saw mentioned.

- what quirks does a spy normally acquire?

Paranoia?

The above info comes from a series of interviews a Polish newspaper did with two retired intelligence officers. Obviously, they probably didn't disclose everything.

Couple thoughts on the subject;

1) Make a distinction between an asset, an officer and tactical support. The chances of having a super agent is ridiculous, and the term 'spy' covers too much.

2) Getting which job would be different in each category. For example a Case Officer would be recruited like any other business, university education with expertise in foreign affairs and language skills. This type of person would be the proverbial chess player, thinking long term and plans upon plans type.

Tactical support would be your paramilitary types, 'sheep dipped' I believe is the term. Spec-Ops guys moved over to the Intelligence services or actual Spec-Ops guys tasked for support.

An asset would be recruited due to what they know and where they work from an Officer and, IMO, would make a good protagonist for a story. Duality is at their heart since they are betraying someone or something by spying for 'the other guys' for money and/or higher personal motivations.

1) Make a distinction between an asset, an officer and tactical support. The chances of having a super agent is ridiculous, and the term 'spy' covers too much.

Ermm... spy = guy who steals secrets?

I know from Burn Notice that they often try to work trough other people rather than themselves (and they call these people "assets").

Well, yeah, I know that its a bit more diverse world but I don't know just how diverse it really is and it really involves.

The guy I have in mind is more of a doer than a planner. He can shoot, he knows his guns, he can steal and he can make a good impression if he has to.

2) Getting which job would be different in each category.

What categories are there?

Zixinus wrote:

1) Make a distinction between an asset, an officer and tactical support. The chances of having a super agent is ridiculous, and the term 'spy' covers too much.

Ermm... spy = guy who steals secrets?

Then you are falling into the same old cliche's.

I know from Burn Notice that they often try to work trough other people rather than themselves (and they call these people "assets").

Well, yeah, I know that its a bit more diverse world but I don't know just how diverse it really is and it really involves.

I like Burn Notice but while it's a step in the right direction AFAIK, it's still James Bond lite.

The guy I have in mind is more of a doer than a planner. He can shoot, he knows his guns, he can steal and he can make a good impression if he has to.

What categories are there?

Again, for simplicities sake, you have the officers, tactical support(paramilitary sort) and assets. I'm hardly a CIA man but I don't think you need to be to realize a division of major job sets needed. Each Operation and/or region will have a subset of staff and managerial elements with supports staff as needed. It would, IMO, be very militaristic in set up and command and control, if you take my jist.

'Guns and shit' would be a tertiary concern unless your character is more of an assassin and/or the proverbial 'cleaner' type. A Case Officer or Contract Agent (if you go off most lititure on the subjects and their lingo on it) would be the managerial staff and 'planners'. Their field work would be dead drops and meetings, let alone actually scouting out and recruiting assests to do the dangerous shit like actually stealing the info you need.

Here, my totally unsupported set up per my own enjoyment of the genre;

Head of Desk. This guy is in charge of the overall theater of operations. Call it by region or specific threat, buck stops here and this dude gets all the analysis and initiates all direct action. He knows all the officers and all the 'agents' involved with his people's operations and does the over all 'large picture' planning with his staff and reports to the headshed. For shit's and giggles, lets say Head of Desk of Eastern Europe. He's in over all charge off all operations in that area and gets all broad spectrum intell collected by any and all sources funneled to him.

He would be in charge of over all human intellegence, electronic intellegence, and for using said information in such a way as to further the governments interests in the region.

Case Officers. These guys are like the Lt. of the Head of Desk. A Case Officer is assigned to specific area's of the overall region or interest. Say, Case Officer of Counter Espionage. This guy gets all relevent info and intell on such issues and is in charge of any and all direct actions pretaining. These dudes can be either in the field or at home base. Or both. These fellows would have official covers and thus protected in the large scheme of things, IE: Deputy Security Consultant for the US Embassy at whatever region they're in. This gives them diplomatic immunity in their actions.

These guys are more a tactical level but as a group working for Head of Desk, need to push for the over all goal.

Contract Agents. These fellows work for the Case Officers and will probably be 'in the field'. These guys are the proverbial 'NOC list' guys. They aren't officially claimed or covered and if caught are disavowed. They are the ones that find and recruit assets under the direction of the Case Officers to further mission objectives and strategic goals as set out by the Head of Desk. Case Officers approve of and authorized assets, but the asset will never meet a Case Officer and deal directly with the Agents. Agents do the dead drops, do the meetings and provide support as needed for the asset to do their jobs.

Assets. These are the HUMINT. Recruited by the Agents, they are either traitors whom the Agents promised money, sex, power, or historically refuge from prosecution or political asylum. A wide variety of assets would exsist. People who work in various jobs would be recruited for information they have or could have access to. Assets who work in various places and could meet various people of interest, here is your basic honey-trap.

Tactical support. These fellows are the paramilitary group in intelligence. Pretty much Spec-Ops as needed, either offensively and/or defensively. Snipers, snatch and grab teams, that sort of shit. I could see that if the Case Officer or such needed ELINT that for one reason or another assets couldn't or wouldn't put into place, Tactical support and/or Contract Agents would do this. IE: putting bugs into place, surveillance of people or targets, that sort of thing.

This doesn't even go into the technically support and the analysis people who would work with all the above. Keep in mind this is my own supposition and just based off of my own musings.

That said, it doesn't work in a vaccum. Specific goals are needed. Sure, a theater of operations can be on idle for a while and do nothing but maintain a good amount of assets in various places that are either slightly active or sleepers, until there is an interest for the government in that area. Nothing ever says all Desks are going at 100% all the time, nor all Officers are pulling off daring operations around the clock.

So being a 'spy' would be a lot more than just one guy, a gun and a shoe phone. They work in networks to further specific goals. You could be an Agent charming a pretty lady who works as a secretary to some mid level government flunky who plays golf weekly with an important government official. Could be important in both the common but still government paper work going through the office, but also as a warning something big is coming if the golf date is canceled.

Or paying a good looking woman to seduce a government employee and then document the encounter to blackmail the employee at your need to get info. Or use all that info to set up an assassination, either by an asset or by the paramilitary units. Or use them all in a 'failed mission' to make the enemy think they're safe or to set up an innocent man for them to hunt in a counter intell operation.

At any level, there will be duplicity and layers upon layers.

As an aside, I'd recommend watching The Good Shepard as well as Spy Games for a depiction of what I've outlined. Not that it makes it any more 'real' per say but it jives with my military training at least.

That's actually a quite useful insight into the business and quite helpful. Thanks, Knife.

From my character standpoint, the most interesting guys are the Technical Support guys. They do work that the Intelligence Officer can't do. How do they work? What do they do?

I like Burn Notice but while it's a step in the right direction AFAIK, it's still James Bond lite.

I watch with the mindset that the creators have a good idea what they're showing but also know they're making a TV show and always look for a good compromise between the two for both practical and artistic/production/viewer's sake/legal reasons. They can't go 100% accurate all the time and do have to go James Bond a bit because they can't do what a "real spy" would do.

It's easier to make Michael have a new-found skill at safe-cracking or video editing than get a new actor for the one time they need it. If they would have done the whole thing 100% or even 75% realistically, the show would be boring.

EDIT: Oh, and I saw Spy Games (that was the one with Brad Pit, I think). I think that was brilliant.

Zixinus wrote:That's actually a quite useful insight into the business and quite helpful. Thanks, Knife.

From my character standpoint, the most interesting guys are the Technical Support guys. They do work that the Intelligence Officer can't do. How do they work? What do they do?

Technical support? I posit they'd be the geeks behind the computers watching and listening to ELINT, you know the proverbial guy with headphones on listing to shit while smoking a cigarette and taking notes. You could do analysts here too, in little cubical s reading reports and making suppositions.

Or did you mean tactical?

What is the average age of an intelligence agent recruit or 'cadet'? Could one be recruited straight out of high school?

Technical support? I posit they'd be the geeks behind the computers watching and listening to ELINT, you know the proverbial guy with headphones on listing to shit while smoking a cigarette and taking notes. You could do analysts here too, in little cubical s reading reports and making suppositions.

Or did you mean tactical?

Yes.

Check out anything on the topic of Reinhard Gehlen.

Zixinus wrote:With Burn Notice recently and my dad giving me Foresyth novels, I have grown a love for espionage-based novels. Up to the point that I have gained interest in it and want to write a stories involving spies and espionage.

As usual, I want to avoid the bullshit. I know that (at least, the older) James Bond movies are a poor source of information. I know that a spy fails when he has to start lugging bullets into his mark. I know that torture is a bad way to get information out of someone. I know that they usually impersonate someone in order to acquire secrets. I also know that their main interest is usually secrets and not assassinations or sabotage.

I believe that Burn Notice does a good, if at least attempted to be honest, job at showing at showing what's it like to be a spy. They show the bad and the boring as much as they show the cool and good.

Like usually, I sadly can't afford to buy books online. Well, at least not right now, especially with Christmas closing in just next week and I like to settle the whole gift thing before the madness starts. I doubt that there is that much useful stuff in the local libraries, besides there is still a cast on my foot and the library well within is in a no-car area.

So, can anyone give me good sources/ links / etc about the subject? Or even just personal thoughts, musing and ideas? Hell, a spy dictionary would be very helpful!

Even a "what to and what not to do" list would be very helpful.

What I'd like to know, is:
- how does someone become a spy?
- what training or background makes someone an ideal candidate?
- how much does combat training and performance matter?
- what happens when the spy retires, either on his own volition or against it?
- how does a burn notice work exactly? Is the portrayal in Burn Notice (the show) accurate or more of an exceptional case?
- what training do spies receive?
- how and when does a spy normally retire?
- what quirks does a spy normally acquire?

I'm going to toss my hat into the ring on this one, and hopefully it will expand on what has already been covered.

First off, spy is rather unclear. Throw the concept of James Bond out, immediately. What we are going to focus on is intelligence gathering, and there are several forms of this. Based on what kind of intelligence you want, we'll know what training you'll want to go for.

http://en.wikipedia.org/wiki/List_of_in ... isciplines

HUMINT - human intelligence - is probably what you think when you think spies. Depending on their training, they might do several things. This can include interrogation work (and the Uhttp://bbs.stardestroyer.net/posting.php?mode=quote&f=7&p=2955913S Army Manual on Interrogation is excellent for this), or it can be debriefing, or it can be sneaking in with the locals and asking questions without being obvious.

GEOINT - geographic intelligence - is google earth, among others. Its eyes in the sky taking pictures. It doesnt even have to be military installations - terrain or infrastructure can be just as valuable to the intelligence specialist.

MASINT - measures and signals - This is radar, among others. They are measuring different waves and beams and making decisions based on that. Its a very technical field, and I havent studied it much at all.

OSINT - open source - This is your google search right here. Think news articles, cia worldfact book, things like that. The demographics of a target country isnt SECRET, but its good to know for background - lets you know about AIDS percentage, children under 18 (and the possibility of child soldiers), things like that.

SIGINT - signals intelligence - again, another technical field, similar to MASINT

There are other intelligences, and most of these breakdown further, but its a good cursory introduction.

That said. High school graduates can do a lot of this, but the course work is often 3-6 (or more) months long. For the more advanced work, bachelors degree (or higher) is required, and has extensive training again. Check out the various intel departments of the U.S. - they list a lot of their requirements.

The biggest thing is your Clearance. This is a number of factors - are you a dual citizen, do you have a criminal record, do you have psych issues, do you have financial problems, anything that might make you prone to sharing secrets. The higher the clearance, the more thorough the investigation.

Combat training matters for some things, and less for others. USMC recon or scout snipers both provide intelligence to the unit they serve with, and are extremely highly combat trained. On the other hand, a cryptographic analyst for the NSA may have never fired a weapon in his life. It depends on what intelligence he is collecting.

When an intelligence operator retires, it is likely that he is put under surveillence for a while, so as to observe if he wishes to sell secrets. Again, his clearance will be checked throughout his career, and poor decisions can result in it getting revoked.

Paranoia is almost a requirement, in moderate degrees.

If you have further questions, feel free to ask.

Shroom Man 777 wrote:What is the average age of an intelligence agent recruit or 'cadet'? Could one be recruited straight out of high school?

The CIA website has a jobs section. Take a looksy. For a professional career in intelligence, I'd assume a Bachelor's minimum in a related field. Linguistics, foreign relations, cryptography, etc...

Zixinus wrote:Yes.

On tactical support (my term not any sort of official term). Like I've been talking about, Intellegence work will need different skill sets per actual objective. Your field guys will be more talkers and smooth operators than badass Bond killers. However, sometimes you might very well need people with more military training. This is your Tac guys. Need a snatch and grab on a guy? Whether to extract an asset after he/she is done with their job, or perhaps it's a new asset you want to interrogate and release later, or perhaps it is someone who is going to disappear. Field agents won't have the skill sets necessary and trained guys for it is necessary. Think of it as Police Detectives follow leads and build cases, they let SWAT storm houses and buildings where dangerous people are. Sure, Detectives have guns and in a pinch will use the minimal training they have on entering and clearing a building of suspects and hostiles, but when something serious is going down they let SWAT because SWAT specifically train for that mission.

A Tac team would train for various missions like this. In military terms, NEO's and TRAP's, point destruction and raids. Spec-Ops already train for these missions so moving them over (sheep dipped) into Intelligence work would be easy, just put new names on the missions. Entering a building and clearing it with CQB would be the same but over all objective might be different. Extraction of friendlies or hostiles would be the same though. Security for various functions would be up their ally as would the obvious assassination and as I mentioned earlier, perhaps just the 'manpower' available to cross train a bit. Breaking and entering to plant bugs, or breaking and entering and then providing security and surveillance while Agents poor over the place for intel. That sort of thing, Tactical support. They support the intelligence personnel by performing tactical missions.


Anyway, I find the whole thought exercise of it to be fun.

I'm a little busy tonight, but tomorrow I'll type up something for you. I actually studied the history and theory of espionage at university so I'll give you an overview from about as informed a perspective as you'll get outside the folk in the intelligence community itself.

Find Spy on DVD somewhere. It's a reality show that aired in Britain about eight volunteers who go through a spy school taught by three former spies, one who had to wear makeup on the show and use a false name to conceal her identity. It's about as good a look into spy school as you're going to get, with the first task being Mossad's "I want to see you on that balcony drinking a glass of water in ten minutes" test made famous by Spy Games.

The volunteers had to carry out their missions knowing full well that, were they caught by law enforcement, they were screwed. And the best part? No prize. The winner got a video that basically said "Congratulations, you could be a spy if you wanted to. Go back to your life."

Also, the British show Spooks (called MI-5 in the US) is very well put together.

You can throw out most of the glamorous stuff you see in James Bond movies, but one thing you should keep in mind is that it probably isn't all that uncommon to employ exceptionally good-looking people as spies. Gorgeous women can turn men into silly putty, an incredibly valuable skill in spycraft. Handsome men can flatter a more normal-looking woman into helping them with something seemingly innocuous. And it's probably not uncommon for two spies to pose as a married couple, which is just a goldmine for storytelling purposes and romance subplots. Couples always look less suspicious and come off as less threatening.

Enforcer Talen wrote:SIGINT - signals intelligence - again, another technical field, similar to MASINT

This is incorrect, according to sigaction(2), which states quite clearly that SIGINT is the interrupt signal, which terminates a process as the default action.

Is it possible for a person straight out of high school ending up under the employ of an intelligence agency? I know that would be weird, but... I want to know!

Shroom Man 777 wrote:Is it possible for a person straight out of high school ending up under the employ of an intelligence agency? I know that would be weird, but... I want to know!

Sure, as an asset. Right out of highschool you just very well might have parents or some such high enough on the food chain that having an intelligence officer trying to turn you isn't too far out there. As an actual intelligence officer? I doubt it, unless you were some sort of MENSA kid in school with a useful skill set.

As an aside; the comment that intelligence work is a lot like journalism is pretty damn close so cudo's to the poster. To that, I'm actually a bit excited to see Keevan's post about it. But it is easy to see intelligence work as journalism for the government. You want answers, even answers to questions you haven't thought of yet, so data collection from multiple sources is vital. Other 'journalists', confidential informants, even sources you track down and pressure to give up the info. To do so, your 'reporters' need a curious mix of charm and relentless dedication to get the info. Stern to their sources so they related and want to give up the goods, but also compassionate enough to know what the source wants and give/offer it to them so you can get your scoop.

Hell, even a sting operation to get info, straight up blackmail, etc... the analogy can keep going and going.

What would happen if there is a guy that appears to be insane after being the middle of enormous clusterfuck-level shoot-out where he sees all of his men, friends and even collogues killed? Nobody can quite get what happened during the shoot-out except that it broke out between two gangs, the reason unknown. Everyone local insists that devils were at work, others suggest a level of ordnance and fire-power used that neither gang could have had access to.

Say, a long term tactical support guy who seen quite a bit of shit like this before. He has otherwise a clean mental record and does not appear to be under any physical mental illness, no record of (intentional) use of drugs. He is shaken by what happened, insists that he saw things that are impossible (things like someone taking an impossible number of bullets and than moving as if nothing has happened, corpses standing up and moving about, people throwing things described as "fireballs", oversized dogs attacking people, etc.

So, do they put the guy in asylum or just threw him into retirement with a slightly reduced pension while assigning him to a therapist?

Zixinus wrote:What would happen if there is a guy that appears to be insane after being the middle of enormous clusterfuck-level shoot-out where he sees all of his men, friends and even collogues killed? Nobody can quite get what happened during the shoot-out except that it broke out between two gangs, the reason unknown. Everyone local insists that devils were at work, others suggest a level of ordnance and fire-power used that neither gang could have had access to.

Say, a long term tactical support guy who seen quite a bit of shit like this before. He has otherwise a clean mental record and does not appear to be under any physical mental illness, no record of (intentional) use of drugs. He is shaken by what happened, insists that he saw things that are impossible (things like someone taking an impossible number of bullets and than moving as if nothing has happened, corpses standing up and moving about, people throwing things described as "fireballs", oversized dogs attacking people, etc.

So, do they put the guy in asylum or just threw him into retirement with a slightly reduced pension while assigning him to a therapist?

Cops have professional shrinks working for them for when cops see traumatic shit, I see no reason why an Intelligence Officer wouldn't need yearly psyc evals and PRN.

About assets: I have heard many rumours about how spy agencies often blackmail people in university and use that material throughout their lives. Assets are often unwilling, I guess.

Like this guy here: http://en.wikipedia.org/wiki/G%C3%A1bor ... #Biography
The Hungarian wikipedia article is also interesting too. Apparently, the guy was haunted by the secret service throughout his entire life.

Cops have professional shrinks working for them for when cops see traumatic shit, I see no reason why an Intelligence Officer wouldn't need yearly psyc evals and PRN.

I just presume that Intelligence agencies are more likely to retire someone early if they are deemed too unstable or too far out for service. After all, there can be nothing worse than someone doing a vital role cracking under pressure. I guess they'd rather retire someone then risk his going nuts when things get hot or at least stressful.

AFAIK, intel officers don't like working with unwilling agents, because they're hard to manage and there's a constant risk they will run to the authorities when you make a mistake.

Paid agents are good, as are ideologically motivated ones.

BTW, on tactical support: Russian GRU ran (still runs?) all their officers through some training with GRU Spetznaz units. Just the way they do things, it would seem - this had the side effect that most officers would be able to run security as well as handle more "normal" fieldwork.

If you don't mind the Casino Royale reference, watch when Bond was approaching the Miami airport, and he told the people at the office to start looking up stuff at the airport that could be attacked and would hurt a lot. Bond didn't have to do any research on what planes were present or potential VIPS arriving/leaving, he just had to follow the guy. The guys back at the main office had the access, no distractions, and found out about the prototype.

So your guy can be a doer, he just has a list of items he needs later on. He goes to the necessary people, gives them the materials, cash, and a time frame. As he needs the item, he goes to the person on that day, and gets it (and pays the other part of the money). He doesn't need to forge an ID, he has someone local do it. He doesn't need to distract a guard, he just bets some girl that she can't get the guard naked in the alley in fifteen minutes (and flashes the cash to do so).

He might not know safecracking, but he can buy a sensitive microphone, a scrambled radio transmitter/receiver, and have a safecracker talk him through the procedure (combined with computer people keeping the alarms off). He won't know computer hacking, but he can be told to place a wireless modem at a certain computer junction (with a video phone in case of problems), and the main office does the hacking over the modem. He just stands guard at the door or searches the trash for additional clues (assuming the cleanup staff haven't already emptied the wastebaskets). Have him do a cat and mouse with the guards, having to get away from the modem to avoid being spotted, then back to the modem to retrieve it (so nobody sees it and immediately realizes what happened).