Which watch should I make my buddy buy for me? AKA, the story of my risk-taking friend and how he has to buy a watch for me by losing a bet

TLDR; good friend is going to lose a bet to me, so which watch should I make him buy for me?

1. Vacheron Constantin Fiftysix Complete Calendar

2. Rolex Daytona Two-Tone Black

3. Gold and Green Moonwatch

4. 5 different Grand Seikos

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So, this should be a story about a bet that I got into with a good friend, and how I'm going to win the bet, and therefore why I need help choosing a watch.  But, those details aren't interesting.  What's more interesting is my buddy's life story, his psychological profile, and how THAT has resulted in me on the verge of winning a bet, in which he'll have to buy me a watch.

This very good friend of mine is highly risk-taking.  He will do things in his professional life that I and all our colleagues consider reckless.  Like, he'll actually speak his mind in meetings, regardless which executives he'll piss off!  

For a keyboard warrior like me, that is unthinkably courageous!  But, him, you see, he was an actual warrior - not of the keyboard variety.   Dude served several tours in Iraq and Afghanistan, as a frontline infantry soldier, so when you're dealing with life and death situations on the daily, maybe all the politics and intrigues of being a paper pusher in corporate America really don't seem like all that much "risk" to ya.  I mean, this dude was the son of a highly decorated general, and then went into the Army as an enlisted infantryman!  

Years ago, when our CEO was interviewing him for a position as Chief of Staff, CEO asked him, "Why'd you do that?"  Friend's answer was, "Well, everybody knew who my daddy was, and I figured they'd treat me with kid gloves.  I didn't want to deal with that noise.  So, I enlisted instead of doing Officer Candidate School."

He did a couple of tours, and always volunteered for the most arduous assignments.  On one occasion, Delta came out to their remote base, and as they often do, asked for volunteers to support them on an operation.  This woulda been me...

Friend obviously jumped at the opportunity.  They ended up in a fire fight, and the enemy was flanking them to take position on some higher ground.  Friend ended up charging some hill, took out a couple of enemy fighters, secured the position, and saved the day.  So, the Delta squad leader invited him to selection for Delta.  He went home on his next leave, told his wife that he was gonna go through Delta selection, and she said, "Wow, that sounds great honey."  She then Googled it, and the results directed her to Black Hawk Down...

... and when she realized what it really meant to join Delta, proceeded to throw a dish at his head.

So, he figured that if he weren't allowed to join the best-of-the-best in the military, he had to go find something else to do, in another field, where he could be the best-of-the-best.  He figured he would go be a lawyer.  

I know, right?  But, come on, he didn't know the first thing about anything outside the military, so let's not judge him too harshly.  

He went to the bookstore, and picked up a couple of Kaplan and Princeton Review books, to study for the LSATs.  Our CEO, who was a former Army Ranger, then said, "Wait...  so, you're in fire fights by day, and then by night you're sitting in your fox hole, studying for the LSATs with a flashlight?"  Friend's response was, "Yes, sir."  CEO says, "And you did well enough on the LSATs to get into Stanford Law?"  Friend says, "Yes, sir."  CEO says, "We're done with the interview."

Now, the only downside to being a former infantryman who went to law school and then goes into tech is that he didn't know the first thing about tech.  Our CEO would email him some massive Excel financial model at 6:30pm, with 50 tabs and 400 lines in each tab, and then the CEO would poke his head out the boardroom door to say, "Yo, can you get me an answer by tomorrow morning?”  

Dude would look like a deer caught in headlights…  CEO was a bit of a prankster, like that.

That's where I came in.  I would see him working valiantly to figure things out, but a lot of the time, a little bit of experience goes a long way.  So, even though I coulda gone home to dinner, instead I'd say, "Yo, man, let me see what he just sent over to you."  And then, I'd tell him, "Oh, CEO wants you to figure out a new pricing structure for our software.  See, we sell perpetual licenses, and he wants to create an option to sell annual subscriptions.  Man, all you gotta do is create an NPV for each, and just make the NPV's equal, and...”

There would always be all the follow up questions, like, "Yeah, but what discount rate do we use?"  Or "But, NPV models have terminal values, so how do I model that?"  And the answers are always just sort of hand-wavey:  "Ah, man, just assume a 10% discount rate.  Why?  ‘Cause 15% feels too high and 5% feels too low."  Or "Dude, we don't need a terminal value.  Let's just assume 5 years.  Cause, none of us will be here 5 years from now."  You know, this sort of thing...

The morning would come, dude would have the model ready for the CEO, and the CEO would be beyond impressed.  CEO would say to me, "How does he do it?  I thought for sure there was no way he'd be able to come up with this!  I mean, he's a lawyer!"  And I would say, "I don't know man!”  CEO thought he walked on water!

It's been many years since that job, and in the intervening years, he's made a lot of money and done really well.  So, we were 3 smoked bourbon bijous into the night, one evening, and he decided to make a bet with me.  And, being the risk-seeking sort, he said that if he wins, he gets my Hyundai Tucson - I was complaining about how much I hated it, and he offered to take it off my hands as a service.  Meanwhile, if I win, he buys me any watch I want.

I think I'm going to win the bet.  In fact, when he proposed the bet, I knew I was going to win.  He's risk-seeking.  I'm not.  The exact details of the bet aren't important.  All that's important is that I'm going to win.  Why?  Because I'm a coward, and I would only ever enter into that kind of bet if I knew there was no way I was gonna lose!

I think the lesson here is that it's good to be cowardly when it comes to bets over expensive watches and such!

So, friends, which watch do I have him buy for me?  

There's the Vacheron Fiftysix Complete Calendar, which is an absolutely gorgeous amalgamation of traditional complication / sporty modern watch...

Honestly, of the “Holy Trinity” the VC Fiftysix line is the only line that appeals to me.  For me, everything else Patek, AP, and VC produce are just…

I could make him get me the two-tone Daytona, if only because non-watch people would know what this is, know that it’s expensive, and then I could tell them that I won it in a bet with my buddy, to really rub salt in the wound!  And, also, so I can be twinsies with @Edge168n...

The green dial gold Moonwatch?  Because, you know, Ryan Reynolds rocked it, so why can’t I?  Amazingly, these are going for nearly 30% off MSRP new on Chrono24!

Or, for roughly the same price as the gold Moonwatch, I could get the following five (FIVE!!!) GS!

Or…  maybe I just make him give me the cash equivalent, and put that cash toward this…

Now, that’s some crazy, outside the box thinking, ain’t it?

Which is it to be???