To make roasted tomatoes: Preheat oven to 425F. Place the cherry tomatoes and garlic in a large baking dish in a single layer. Sprinkle them with Greek oregano, sea salt, freshly cracked black pepper and brown sugar. Mix well. Roast for 40 minutes.
To make the Parmesan potato croquettes: Boil the potatoes in salt water for 10 to 15 minutes, or until fork tender. Strain. Sauté the green onions and garlic in extra virgin olive oil for a few minutes until garlic is golden and onions are translucent. In a big bowl, combine the onion and garlic mixture with the boiled potatoes. Add Parmesan cheese, sea salt, freshly cracked pepper, and mash together. Cover and refrigerate for 30 minutes. Roll the chilled potato mixture into fingers. Dip the fingers in beaten egg then coat them in Italian season bread crumbs. Fry the croquettes in 1/4 inch of 375 degree olive oil for 30 seconds, until all sides are equally crispy and golden.
To make the filet mignon: Season the steaks with a pinch of Montreal steak spice. Heat the canola oil in a frying pan over medium-high heat until almost smoking. Sear the steaks for 2 minutes on each side. Reduce the heat to medium-low and cook the steaks for another 2 minutes per side. Tent the cooked steaks in aluminum foil and let them rest for 10 minutes.
To make the balsamic syrup: Heat a pan on medium-high heat, add equal parts maple syrup and balsamic vinegar, and stir for 3 to 5 minutes until the sauce is bubbling and slightly reduced. Serve immediately, drizzled over the filet mignon.