Jailer

Jailer

You read all kinds of stories where the husband tells the cheating wife that he doesn't want to have to watch her every minute going forward to make sure she keeps her promise to never cheat again.

What would happen if he was up for that?

---

My name is Jeff Cross, JC to my closest friends. And today I am going to let my wife, Sandy, out of jail after eight years. Three factors have come together to make it possible to set her free.

The first is what I do for a living; I'm the VP of Cybersecurity for a large American software company. The trigger for my wife's release is entirely related to my work. Two weeks ago my boss, the Chief Technology Officer, and good friend Tom, called me into his office to give me some good/bad news. Our company had been acquired by an even larger multi-national. And I'm going to be out of a job as they have their own head of Cybersecurity who will be absorbing my department, and all my people.

Second is that I have a personality quirk that I share with many in the support side of high tech; I tend to "set it and forget it". Without getting too technical (more on this later) this means that in many, many areas of high tech we want to arrange things such that one doesn't have to watch over a system, process, or application all the time. We want to set up monitors, alarms, or other automation to do the watching for us. Think of it this way, you buy an automated sprinkler system for your lawn so that you don't have to pay attention to when it needs watering. The system just does that every Tuesday, Thursday and Saturday, just the way you set it up. The result is a lawn that stays healthy and green.

The third factor is the other side of the 'set it and forget it' coin, if something is very important, I become hyper vigilant. Again turning to gardening, even if you have a top of the line automated sprinkler system, you might still baby your orchid plants. You know the drill- morning sun, just enough water; make sure they live in a protected spot during the winter as frost might kill them. In other words, you spend a lot of time and attention to this high value plant. After all, your orchids are the envy of the whole neighborhood. You might even buy some gadgets to measure the health of the soil or the nutrients you add to the plant's water.

Ok, if you're still with me here's how it all comes together and how it relates to my wife's "incarceration".

Like most software companies in the Valley, I get stock grants for being a good employee. And when you're like me and want to always excel, a stellar performance review usually comes with a raise and a bonus. In my case I've almost always gotten good to great reviews, I'm not some genius, but my performance is like the orchid, something I pay a lot of attention to - because it results in a bigger paycheck and bonus. When you're raising a pair of kids that need to be fed, housed and educated, having enough to give them a good life is a big deal.

Anyway, while I have always paid attention to the salary side of my comp, I have hardly ever given thought to all those stock grants. As I have moved from job to job, I've always done the same thing with my stock administration - I've 'set it' to 'sell to cover'. Which means that when a stock grant matures, the administration sells enough to cover the taxes and then the remaining stock is mine free and clear. It's automatic, I never have to think about it, and I never have. So in the twelve years I've been with my current company I have a boatload of stock that's all mine just sitting in my brokerage account. My wife and a couple of buddies have nagged me over the years to do something with that stock. And I've promptly forgotten that conversation the minute it's over. Again, my attention is elsewhere, and what's the big deal anyway?

So, the big multi-national has decided that to make their lives easier, they're not going to convert any existing stock in our company to theirs. They are just going to cash out all the stock us peons own and go forward from here. So the news is bad and good; I'm out of a job, and I'm getting cashed out. This means that the pile of stock I've accumulated just became a pile of money. Like retire at 54 size pile of money. My dumb-ass never paid attention to my stock means that I'm an overnight genius. Who knew?

And retire I am most certainly going to do. No longer will I have to be available 24 by 7 in case a bad guy tries to break in, or a hacker gets a clue. Nope, no more looking at threat intelligence reports, or consolidated graphs from our Operations Center about the state of our perimeter. I'm never going to have to conduct another Simulated Incident table-top exercise for bored Execs who just want to get back to playing DnD on their office laptop. I'm done.

And I am going to stop monitoring my wife's comings and goings 24 by 7. Today I'm going to have a chat with her and let her know that she is free to choose. We can go our separate ways, or we can ride off into the sunset together. She doesn't know she's been under close scrutiny for eight years, she's never suspected a thing...

----

We were sitting in a corner table at Emile's, the toniest restaurant in town. I had on my best suit and Sandy was dressed to the nines. I had told her I had a really big surprise for her and I was going to spring it on her tonight. I was being coy since I had told her and I kept quiet until the waiter had popped open the Veuve Clicot and filled both our flutes.

"We have been married for twenty nine years, and we'll be celebrating our 30

th

next year. I wanted to acknowledge all that with a little gift and a couple of surprises." Out came the long slim case and I presented it to her. When she opened it she gasped at the sight of the tennis bracelet.

"Oh my god, Jeff. It's wonderful, it's so shiny and so many diamonds."

"I hope you like it; I had it made especially for this night. I know we had our anniversary a couple of months ago, but my surprises have come afterwards. The first is this present. The second is that I have been bought out at work, we've been acquired and all those shares I never did anything about have been magically transformed into a huge pile of cash. Enough for us to retire on."

"Jeff that is wonderful news! I thought we still had a few years to go, I guess all of our savings put together with your windfall will make everything easier."

"That's exactly what I was thinking too. But here, let me explain some unique features of the bracelet to you and then we can get to my final surprise."

"It's so beautiful Jeff; I noticed it was a bit different than what I expected. What are these two colored diamonds for?"

"If you start counting from the clasp, you'll see that those two colored stones are in the second and fourth positions. Those symbolize our two children; they were born in our second and fourth years of marriage. Then if you keep going you'll find that there are a total of twenty one stones all of the same size. Starting with the twenty second stone the next eight are slightly bigger. Those symbolize the last eight years. You were a really good wife until then, but you really upped your game these last eight years.

If you look closely at the twenty first stone, you'll see that it has a noticeable flaw in it. There's a good reason, I picked that stone out specifically for the flaw. You did a great job of keeping the promise you made to Terry when you broke up with him to be 'the best wife anybody ever had'."

"Oh my god, you knew about that! I'm so sorry Jeff, I had hoped to take that secret to my grave, and I never meant to hurt you! And here you knew all along. Are you going to divorce me, have you been playing me all this time!?"

"Not necessarily, I'm actually going to set you free. You see I can verify that you have been faithful since Terry. I know first-hand that you've treated me a lot better, both in and out of the bedroom. No, I'm referring that not only am I retiring from my job; I'm also retiring from being your watchdog. You see I've had you under constant surveillance for the last eight years. I know every move you've made, every conversation you've had, everything you've done has been scrupulously documented. I know you've kept your promise."

"What, why, how!?"

"It was simple really, and didn't take all that much effort. You know what I do for a living, and you've no doubt heard me describe how my job is to protect the 'crown jewels' at my company. I won't bore you with the details but I treated you the same way, you're my own 'crown jewels'. I used all the same technology and techniques that I use in my work on you. Everything you do has been recorded and analyzed to detect anything strange. You've been monitored to ensure no bad guys tried to break in again. And all of that information has been consolidated into graphs and a report that I look at every morning. And there are special alerts to detect if anything new and unexpected happens, and if so I get paged immediately."

"But all of that ends today. I am retiring from being your watchdog, your jailer. You are free to come and go as you please. I've already turned off all the devices planted in your purses, shoes, your office, and your car. I want a quieter existence from now on. I want to unburden myself of all that noise I have to deal with at the office, and I want to do the same with you too. I want some peace."

I asked for Sandy to extend her hand. "Consider this bracelet a reward for being a great wife and mother. I think you've done wonderfully, I have been very, very happy all these years. But now that you know that I knew about Terry, and that I have kept tabs on you all this time you get to make a decision. You can have some peace too. You can relax now; you don't have to worry about me finding out, because now you know I always have. And you can decide if you want to stay married to me. Half of the pile of money I just received would be yours if you divorced me. It would be enough for you to start over anywhere, or with anyone you want. You too could be free and at peace."

"This is all too much; you gotta give me a minute Jeff." Sandy drained her glass and I refilled it. "Ok I need you to start over at the beginning. How did you find out about Terry and me? I swear to you there has been nobody else since Terry, I have made sure to stay focused on you, my husband, my family. I haven't let myself get into any situations that might lead me astray. I've kinda become an Ice Queen at work too, I keep it all business."

"Yeah I know, we make quite a pair. Don't frown; I'll explain all that in a bit. As to how I found out, I didn't. I had no clue that you'd been cheating on me with Terry for two months. He came to me; he confessed all of it to me the week before he left for Chicago. He told me how he couldn't live with the guilt, that he thought he was better than that. It was quite a scene. He even brought his best friend along to make sure I kept my cool. For that I am grateful, otherwise I'd probably be wearing orange today and drinking jailhouse hooch instead of this awesome bubbly." I raised my glass and took a sip.

"JC, I don't want a divorce; I do want to ride off into the sunset with you. Not a day has gone by that I don't regret stepping out on you, on cheating on our wedding vows. I have felt so guilty, I've beat myself up over and over about how I could have been so stupid, so self-centered. I was seeing a therapist instead of going to the gym on Tuesdays for a couple of years. Hah, but you knew that already didn't you. Has nothing I've done escaped your notice? I'm not sure how I feel about your invading my privacy like that, wow. You've really known about everything I've done, every conversation?"

I nodded, "Yes, like I said it was really quite simple to set up. I did it just like I would for any company. There are a couple of virtual servers out in the cloud, in a private account, and some smart software that consolidates all the data about you and make it available to me. I can look at that stuff on my computer anytime I want. It looks just like any of the other graphs or reports I already get. In fact you wouldn't know to look at it unless you knew what the title meant, BWAEH -Best Wife Anybody Ever Had."

"So Sandy, let's back up and relive that Thursday eight years ago, let me play you the tape, I'll fill in some of the details..."

"Hi JC, are you free for lunch today?"

"Hi Terry, sure man, I could use a burger and a beer. What time?"

"Noon at Jack's on Main. And JC, can you please not tell anyone you're meeting me? I've got some private stuff to discuss and I want to keep our meeting on the QT."

"Ooh, a mystery. I love a good mystery. See you at noon."

I found Terry in one of the booths towards the back of Jack's, the one nearest the kitchen. "Hey man, haven't seen you around the neighborhood barbeque lately. Good to see you." I turned to Hugh, a friend of Terry's I'd seen around and held out my hand. "Hugh, how are you. I didn't know you'd be here too." Hugh took my hand and just nodded.

"Thanks for meeting me JC. Yeah, I've been making myself scarce the last couple of weeks. Part of that is that I've taken a promotion and transfer. I'm moving to Chicago, in fact the movers are packing us up this weekend and we're getting on a plane Monday morning."

"Wow, I didn't know. Or rather, Sandy probably mentioned it and I wasn't paying attention. How does Stella feel about moving to the mid-west?"

"She's actually looking forward to it. We'll be closer to her sister and the cost of living is better than the Valley. Which brings me to the other reason I'm moving. You see I'm a chicken shit and a coward."

"Terry, what the fuck are you talking about man? I've known you for how many years? Our kids have played together, and Sandy and Stella are best friends. What gives?"

Hugh put a supportive hand on Terry's shoulder and nodded to him. "JC I'm moving away because I've just broken it off with a married woman I've been having an affair with. It only went on for a couple of months but I just couldn't keep cheating on Stella, it was eating me up inside. Hugh is the only other person I've told, and now I'm telling you."

"Holy cow, an affair. That is fucked up man, how could you do that?"

"I know, I know. I won't bore you with the details, it just started and it kept going. But it got to the both of us, we both decided that we needed to break it off and dedicate ourselves to being the best spouses we could be going forward."

"Does Stella know? Poor thing, it must be crushing her."

"No, Stella doesn't know and she never will. I'm going to take this to my grave. And Hugh is my best friend, he can keep a secret. That's why I fought for the promotion and move. I want to get out of Dodge and never have to see the woman again. It's best I make a clean break and be a good boy from now on."

"Terry, I gotta say I'm shocked. I always thought of you as a stand-up guy. But I guess nobody's perfect. But why tell me, we're good buddies but I don't rate like your BFF Hugh."

Terry had trouble making eye contact at that point and he got another shoulder squeeze from Hugh.

Ding, ding, ding. The penny dropped, "Say the words Terry, I need to hear you say them." The Ice Man had suddenly awoken, he become hard; his entire focus was on Terry's face. Nothing else in the universe existed in those moments. The Ice Man cometh.

"JC, I'm so sorry man. I didn't, we didn't plan it. It just sorta happened and then it took on a life of its own." Still no eye contact.

"Say the words Terry." The Ice Man's voice was sub-zero, he had never been so angry in his entire life.

"JC, it was your Sandy. I had an affair with Sandy. We broke it off two weeks ago."

You never know how you're going to react in critical situations. But again, going back to my job, I've had lots of practice in emergencies. They're part of the job, and I'd developed an ability to bury my emotions and become the Ice Man during a crisis. I got a lot of respect for that in my professional world.

The Ice Man sat back into the seat, "OK Terry. You need to keep talking. And I suppose Hugh is here for both moral support and to make sure I don't rip out your throat?"

"Yeah, like I said I'm a coward. Look JC, we were only together less than a handful of times. And I swear to god Sandy said at the end that she regretted every minute. She was distraught when we broke up. She swore she was going to make it up to you, that she'd be the best wife anybody ever had from now on. She didn't, uh, doesn't want to lose you and the life you guys have."

"I don't think you're a coward Terry. It takes a lot of balls to tell a man you've been banging his wife. And I want to thank you for bringing Hugh. I think he's kept me outta jail and Stella from being a widow. But why tell me now? Why couldn't you just slink your chicken shit ass outta town and nobody would be the wiser?"

"It's a mixture of things, I really, really feel guilty. I didn't think I could do that to another guy, and a friend to boot. I'm hoping that somehow by telling you I'll be able to look at myself in the mirror. You've been pretty good friend; I feel that I owe you. And quite frankly, you're a scary guy. You're one of those Cyber guys, I don't want you coming after me with some high tech shit and ruining my life. I've got a family to think about."

Just then our food arrived and the Ice Man took a long swallow from his beer. Thank goodness it was ice cold. "And what makes you think I still won't do that. Did you think your coming clean was somehow going to protect you from my wrath?"

"Yes, that's exactly what I'm hoping. Let me go, I've chosen exile in fucking Chicago man. And near Stella's sister for Christ's sake. I'm going to be punished enough with this move regardless of the promotion."

The Ice Man smiled, "OK, let's say I let you live, let you take your banishment to Chicago. What did you expect me to do about Sandy; did you think that your telling me would make me go easy on her? What were your thoughts there?"

"I don't know man, I don't know. But I do know that she loves you, she was terrified when we last talked a couple of weeks ago. She went on and on about how she couldn't live without you and how could she have been so stupid. I believe her when she said she'd never, ever let herself be tempted again. She really tore me down too. Said I wasn't worth it, that I wasn't half the man you were. That really stung, but it did make me take a long look at myself. I didn't like what I saw."

The Ice Man took a bite out of his burger, "Eat up guys, your food is getting cold. Give me a minute to process all this." Terry and Hugh glanced at each other and nervously tucked in.

The Ice Man was indeed processing all this new information. An advanced persistent threat had revealed itself as it was exiting the system. How much damage had been done? Could the entry points be re-secured? What measure could be put in place to ensure another threat didn't cause damage again? Were there other threat actors present? Who else knew about this fucking mess!!?

"You say two months and just a few times. Who else knows about this? Are you sure nobody saw you together with Sandy? Think man, does anybody else know!?" The Ice Man was indeed scary.

That's when Terry crumbled. He didn't exactly cry, but he covered his face with his hands and was shuddering. "I'm so sorry, I'm so sorry. I thought I was better than this, I thought I was a stand-up guy. We were really careful, like I said it wasn't that many times. And never in our own beds, we wouldn't do that."

The Ice Man chuckled, "Well, that's mighty noble of you. No fouling your nest, eh." Click, click, and click. The pieces fell into place. Minimize the fallout, protect the assets, don't overspend on unnecessary measures.