Dear Mr. Cashman, a miniature trade deadline is about to crash; are you ready?

Dear Sir,  

For the sake of a parlor game, let me tell you what you already know.

You have until Friday to finalize the Yankees' 40-man roster before the December Rule 5 draft. Supposedly, you have too many unbelievable, can't-miss, super-prospects to protect, so you're in the market for converting a few of them into an established star. You know... the usual move this time of year, a holiday tradition!

According to the Internet, you are talking with Oakland about obtaining 1B Matt Olson for a bundle of prospects and Lovable Luke "the Lug" Voit. 

Well, I won't tell you what to do. Why bother? You never listen. You look at me with those puppy eyes, and you nod, and I want to believe that you are absorbing my wisdom. But I know better. You're humming a tune in your head. You've been angry at me since Jesus Montero - yes, I was wrong about the human Ice Cream Sandwich, but Pine Tar Pineda wasn't exactly Cy Young, was he? And Sonny Gray? I mean, come on... so, yeah, I won't tell you what to do. But I can say this:

Once you cut your first deal - whatever it is - you better have the follow-up moves locked and loaded, because all Hell is going to break loose. 

Let's say you obtain Olson, a fine player who should solve our 1B woes. Immediately, that undermines any bidding war over Freddie Freeman (who, let's face it, will probably will stay in Atlanta anyway) and Anthony Rizzo (who - hmm - we know is coveted by Boston.) With the Yankees out of the 1B market, the Redsocks might move quickly on Rizzo, or re-sign Kyle Schwarber, or both. Either way, they get their 1B without a checkbook duel with the Yankees. It might happen within hours. 

By then, you need to be well into your next move: Finding a shortstop. To get Olson, it's almost a certainty that either Anthony Volpe or Oswaldo Peraza - our best two prospects, both shortstops - will go to Oakland. That leaves the Yankees with a potential long term hole at SS. Instead of two prospects competing against each other, we'll have one, and the odds of a farm system solution wither dramatically. The notion of a stopgap, one-year SS - you know, Didi or Elvis - becomes much less viable.

Thus, if you swing that deal for Olson, signing a big name SS becomes The Immediate Priority. You better know who you want - Correa, Seager, Story, the cast of Glee, whomever - because the stampede will have begun. And once you make that offer, and once you get your shortstop, every other team in baseball will know that Elvis has left the building. North to Alaska, go north, the rush is on! The SS market will explode. 

By then, you need to be into your next move - the hole in CF. (Note: Aaron Hicks is now officially an afterthought. Your 40-man roster will have two or three openings. You can fill them with prospects or go after a CF, or pitching, pitching, pitching. 

Whatever you do, sir, keep your powder dry. A miniature trade deadline is about to crash. I assume you are ready? Right? Hello...?