Stuffed Flank Steak (or Poor Man's Beef Wellington)

I know.  It's been a while.  In fact, since we've last seen each other, even the last digit on my post timestamps have decided it was time for a change.  And what do I have to show for it?  What do I have, at least, to apologize for the entire one and a half months of cooking in secret?

I did start writing a post on New Year's Eve with the ambitious and haughty goal of making it before 2013, a poor decision seeing as it was already 11:30 and I had just worked for eight hours and driven for two.  It had something to do with sorrys and thank yous and the curse of "well-roundedness."  There were even a couple of quotes from Great Gatsby in there (don't ask).  But mostly it was written by a very tired (albeit well-intentioned), frantic, uninspired person.  And it showed.
When really, it comes down to this:

I had just taken a seat at my favorite spot at the restaurant - the community table - and was ready to indulge in my asian chicken salad and 30 minutes of pre-dinner-rush bliss.  A tall, slender man with speckled gray hair was finishing his meal diagonally across from me.  I gave him a polite smile before taking my first bite when my boss, Chef, came over to say hello to this person, apparently an old customer, or friend, or both.  Eavesdropping as I always do, with unintentional attentiveness (because this is totally normal), I followed the twists and turns of their conversation as it went from champagnes (the "real stuff") to struggling restaurant businesses to the perfect seafood stock.  As I gleaned little nuggets of information along the way, carefully taking mental notes (Le Grande Dame for when I'm ballin', don't mix fish with crustacean, you don't need the heads for flavor, don't boil it for longer than 1.5 hours) the topic came to a stop at squash soup.  I have to admit that by this point my attentive ear was very much intentional. Apparently this guy had just been trying to make a kabocha squash soup at home, but while it had the smell and consistency that he was looking for, it was lacking in flavor.  He tried some crisped pancetta over the top (Chef: "Makes sense") and kept adding butter and cream to give it that umph he was after, but to no avail.  Thats when Chef said,

"The secret to squash soup is ____."

That guy: !!!
Me: !!!

"Yup.  You wouldn't think it, but just a little in there adds a layer of flavor; you can't quite put your finger on it but it's what makes it really good.  It makes sense - they're actually old friends, ____ and squash."

I wouldn't be exaggerating to tell you that, at that moment, I felt as if I'd struck gold.  And you might think me a little lame, or crazy, or both, for getting so worked up about the secret to a good squash soup, but you know what? That's perfectly fine.  Because here's my point: food still excites me.  I have other hobbies, like knitting, or music, or design, or photography (go ahead, roll your eyes), and a number of other things in which I've dabbled but never surpassed mediocrity.  Sometimes my time and interests and desires are spent over a little of each rather than focusing on just one.  ("Sometimes" here largely means the last one and a half months.)  But that day, that conversation, that word* reminded me that food is still what gets me going way more than anything else, way more than any new knitting pattern or strumming method or Photoshop technique could, at least for now.

So I think I should invest a little more time in it, don't you?

And what better way to start than by sharing this special occasion recipe with you?  Flank steak, rubbed with generous amounts of garlic and oregano, stuffed with layers of prosciutto and a comforting mushroom and chestnut filling worthy of any holiday (or, since I'm a little late for that, any Valentine), is rolled, tied, and seared in a hot pan before finishing off in the oven, resting in its juices, and being sliced into pretty pinwheels beside equally beautiful sides.  This is definitely a great way to give a cheaper cut of steak some serious wow factor.  Because I took some notes from Chef Gordon Ramsay for the filling, I like to think of it as a poor man's Beef Wellington.  That way, you can spend the money you saved on a beef tenderloin (~$20/lb) and puff pastry (~$4/box) on a nice Christmas gift (did I say Christmas? I meant Valentine's).

I served mine for Christmas dinner with some homemade focaccia (bread baking might as well be an enigma to me, but this recipe is nearly foolproof), mashed roasted garlic cauliflower, and the roasted brussels sprouts I am so fond of.  I want to post up the cauliflower along with this, but when I made it in the rush of Christmas afternoon for five very hungry people, I didn't take enough notes (again) on the seasoning measurements to give you an accurate recipe...yet.

* But why all the blanks?  I didn't want to reveal it until I gave it a test-run myself first.  Can't wait to see if it works!

Stuffed Flank Steak (or Poor Man's Beef Wellington)
generously adapted from A Spicy Perspective and Gordon Ramsay's Christmas Beef Wellington
Serves 4-6

For the filling:
2 Tbsp butter
1 Tbsp extra virgin olive oil
8 oz. wild mushrooms (I only had white button, which were still fine), finely chopped to the consistency of coarse breadcrumbs
5 oz. chestnuts, cooked, peeled, and finely chopped to the consistency of coarse breadcrumbs
2 cloves garlic, minced
1 tbsp fresh rosemary, chopped
1/2 cup dry white wine
Salt and pepper, to taste
4 slices prosciutto

For the steak:
1 1/2 lbs. flank steak (I bought about 2 1/2 lbs, which were two pieces of steak, and only used one which was about 1 1/2 lbs and 8"x11" inches in size; this made 7 1" pinwheels)
1 Tbsp garlic powder
2 tsp salt
1 tsp black pepper
1/2 tsp red pepper flakes
1 tsp dried oregano
2 Tbsp butter
Kitchen Twine, for wrapping and tying

Make the filling: Bring 2 Tbsp butter and 1 Tbsp olive oil to medium heat in a large skillet.  Add mushrooms and chestnuts, and sauté until softened, about 10 minutes.  Add the garlic, rosemary and white wine, and cook until the wine has completely absorbed, about another 10 minutes; the mixture should hold its shape when stirred.  Set mushroom filling aside in a bowl to cool.

Prepare the steak: Combine garlic powder, salt, pepper, red pepper flakes, and dried oregano in a bowl and mix well.  Place a piece of plastic wrap onto a flat working surface, and lay the steak over it.  Evenly divide and rub mixture onto both sides of the steak.  You might not use it all, but make sure that both sides are generously covered in the seasoning - no bland steak here!  Place another sheet of plastic wrap over the steak.  Using a meat mallet or a rolling pin or your fist (but preferably not your fist), pound the steak out as close as to a 9"x12" rectangle and 1/2" thickness as possible.  Lay the slices of prosciutto over the steak, leaving a 2-3 inch margin along one long edge.  Then spread the cooled mushroom filling over the prosciutto, leaving the same margin. Starting with the long edge covered in ingredients, carefully and tightly roll the steak.  Tie the rolled steak in four places with kitchen twine.  Rub the outside one more time with more seasoning.  At this point, make sure the steak fits into the skillet you're going to use; if not, trim the ends off a little so that it can.

Cook the steak: Preheat the oven to 350° F. In a large oven-safe skillet (cast-iron would be your best bet here), heat 2 Tbsp butter over medium-high heat.  When the pan is nice and hot, carefully place the steak in it and sear, rolling about every 2 minutes, to brown all sides - about 5 to 8 minutes in total. Transfer the skillet to the oven and bake until cooked through - about 20 to 40 minutes, depending on the size.  [Note: I over-seared mine - the pan was too hot and the outside of my steak was a very dark brown - so I only baked it for 20 minutes, which resulted some medium rare pieces and some medium pieces.  Because flank steak is a leaner cut of meat, it tastes best cooked rare to medium rare.  You can use a meat thermometer to make sure you cook the steak to your taste: 125° F for rare, 130° F for medium rare, and 140° F for medium.]  Carefully transfer to a dish and tent with foil; let the meat rest for at least 10 minutes before slicing into 1-inch pieces.