Prosciutto Wrapped, Mediterranean Stuffed Chicken Breasts with Butternut Squash Puree


We had chicken breasts in the fridge.  And that was about it.  Typically I would turn to my pantry, pull out some spices and make a rub for fajitas.  But, without onions, bell peppers or tortillas on hand this wasn’t going to work.  So my fridge and I had a nice long stare down.
Me: I know – I have bread crumbs… lets get frying!
Fridge: Haha – I don’t have eggs, good luck with that!
Me: Well then I’ll grill the breasts and do something with pasta.
Fridge: If you make pasta for your husband one more time he will run away.  Seriously.
Me: You’re right… come on, give me something.  Please???
And then I spotted the prosciutto.  Aha!  I’ll wrap the chicken – delicious!  Now I was excited.  This is typically how it goes for me.  If the lightbulb turns on, I know I can make something worthwhile.  We had some mozzarella that needed to be used.  Add a few of my pantry standards and a mediterranean inspired stuffing was born!
My butternut squash was also looking awfully lonely on the counter, so he was brought into the mix and really provided a great partner for the salty, rich chicken giving a creamy, mildly sweet consistency to the plate.  So now when I have chicken breasts and am in doubt I will stuff them!  Take that fridge :)


Roasted red peppers, artichoke hearts and kalamata olives.  ALWAYS good together.  I added crushed red pepper for some heat, panko to help absorb the excess liquid and lemon to brighten things up.  And of course, garlic is always invited to the party in my kitchen.
Garlic – a pantry standard.  I can never have too much!



Kalamata Olives, how do I love thee… let me count the ways…

A pinch of red pepper flakes…

Basil, my bff…

Two palm-fulls of panko…

Add the juice from half of a lemon and mix.


Taste, taste, taste along the way.  This particular mix will not need salt or pepper.  There is plenty of saltiness coming from the olives and the prosciutto will round out the salt quotient of the dish.

On to the chicken!  I cut the breasts in half and trimmed off the excess and then took my paring knife and made a two inch cut into the fattest part of the meat.  Go about one inch in but be careful not to cut through to the other side.


I think mozzarella is perfect for this type of stuffing.  It will melt nicely without becoming a cheesy mess in the pan.  I used two 1/4 inch slices per chicken breast.


Use your hands to add the stuffing.  It’s really the easiest way and you can make sure it gets in every corner of the pocket.

Lay three pieces of prosciutto out on a cutting board.  It’s thin and can be hard to work with so be patient.  Place the chicken toward one end, with the stuffing facing out.  Pull the excess prosciutto up over the stuffed side of the chicken breast and roll.


Pull the bottom ends up and make sure the stuffing is completely covered.

Place a pan on the stove and turn the heat to med-high.  Let the pan heat for a minute or so and then add olive oil.  Allow the oil to heat for a minute or two, until you see rings begin to form but not until smoking.  Add the chicken breasts carefully and cook on each side for approximately 6 minutes, depending on the thickness, turning once.  When in doubt, use a thermometer.  You’re looking for 160 degrees in the thickest part of the meat.
I typically adjust the heat as I go, but it is important to start off hot so you can create a nice sear.  If you put the chicken in the pan before the oil is hot enough then you won’t get a crust.  I really use my ears for this – you want to hear a lot of sizzle when it hits the oil.  This will cook for approximately 12 minutes total, so watch it carefully and turn the heat down if needed, especially if the pan looks like it is getting dry.

Now for the butternut squash, which is by far my favorite fall/winter veggie.  It is sooo yummy roasted, pureed, sauteed… you really can’t go wrong.  It takes a little work to get into it though, and a steady, firm hand.  I usually start but cutting it in half and then removing the the ends.


Take your knife and cut the skin off, just running down the sides.  The bottom half is a little trickier since it is curved.  Just move your knife along the body of the squash and then go back to trim off any excess that you missed.

Cut the bottom in half and scrape out the seeds and fibers.  I am not a fan of this part… it makes me think of carving out pumpkins, which I have never enjoyed, even as a child.


Cut the squash into one inch cubes and place in a pan, adding salt and water to cover the squash half way.  Put the lid on and simmer for 10 -12 minutes.  They are ready when they are tender and smell oh-so-yummy!  When making this with the chicken, begin the simmering right after you put the chicken in the pan.  The timing should work out well.


Into the food processor they go.  A blender will work well or, if you don’t have either, a potato masher will do.  But first – add a pinch of nutmeg, kosher salt, freshly ground black pepper and a tablespoon of butter – plus a little more if you’re like me :)

Final touch – a tablespoon of good honey.  Then give it a whirl!


The finished product – so delicious!  I am adding this to my dinner party menu list.  You can prep and stuff the chicken ahead of time as well as cut the squash into cubes.  All you will need to do to get dinner on the table is put the chicken on the stove and steam the squash!


Now the only question is, what will I stuff the chicken with next time… we’ll just have to see what my fridge has to say!
Continue reading for the ingredient list and step-by-step directions!

Prosciutto Wrapped, Mediterranean Stuffed Chicken Breasts with Butternut Squash Puree

Serves Two

For the Chicken:

  • one roasted red pepper
  • four small pieces artichoke hearts, drained
  • two cloves garlic, minced
  • one quarter cup kalamata olives, pitted, and minced
  • five basil leaves, chopped fine
  • one half cup of panko breadcrumbs
  • juice from one half of a lemon
  • four one-quarter inch slices of fresh mozzarella
  • two boneless, skinless chicken breasts
  • six slices of prosciutto
  • one tbs olive oil
For the Squash Puree:
  • one medium butternut squash – 1.5-2 pounds
  • pinch nutmeg
  • one quarter tsp kosher salt
  • one eighth tsp fresh group black pepper
  • one plus one half tbs unsalted butter
  • one tbs good honey
Starting with the chicken, combine the first seven ingredients in a bowl and set aside.
Using a paring knife, make a two inch cut into the fattest part of the meat.  Go about one inch in but be careful not to cut through to the other side.  Place two slices of the mozzarella into each breast.  Using your hands, add the pepper & artichoke stuffing.  Lay three pieces of prosciutto out on a cutting board, vertically, side by side.  Place the chicken toward the top end of the slices with the stuffing facing toward the rest of the prosciutto.  Pull the top end of the prosciutto slices up over the chicken and roll the chicken toward yourself, sealing with the bottom of each slice of prosciutto.
Place a pan on the stove and turn the heat to med-high.  Allow the pan to heat for one minute and then add one tbs olive oil.  After the oil has heated up for one minute and is forming rings but not smoking, add the chicken breasts.  Cook on each side for approximately six minutes, turning once.  Cooking time may vary based on the thickness of the meat.  You want to make sure the temperature reaches 160 degrees.
For the butternut squash, begin by cutting the squash in half and then removing the top and bottom of each side so it sits on a flat surface.  Using your knife, remove the skin, running the blade along the body of the squash.  Scrape out the seeds from the bottom half with a spoon.  Cut into one inch cubes.
Put the squash in a pan and cover half-way with water.  Add salt, bring to a boil and then cover, reducing the heat to a simmer.  This will take 10-12 minutes.  Test the squash with a fork and make sure it is tender.
Place the cooked squash in a food processor or blender (be careful when pureeing food that is hot – allow to cool slightly) and add the final five ingredients.  Puree until smooth and serve immediately.

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