Whisk together 1 tablespoon olive oil, brown mustard, garlic, 1 teaspoon salt, cracked pepper, and port wine in a bowl; pour marinade into a resealable plastic bag.
Add the beef, coat with the marinade, squeeze out excess air, and seal the bag. Marinate in the refrigerator for at least 1 hour
Bring Cabernet wine and dried cherries to a boil in a saucepan, reduce heat to medium, and cook, stirring occasionally, until wine has reduced to about 1/3 of its original volume, about 20 minutes.
Dissolve 1 teaspoon sugar and 1/4 teaspoon salt into the wine mixture and pour in extra-virgin olive oil. Remove from heat and let dressing cool.
Preheat oven to 350 degrees F (175 degrees C). Grease a sheet pan.
Toss pecan pieces in a bowl with water, 1 tablespoon sugar, and 1/4 teaspoon salt in a bowl until thoroughly coated. Spread coated pecans into the prepared sheet pan.
Bake pecans in the preheated oven until the coating adheres to the nuts and pecans are fragrant and brown, 15 to 20 minutes.
Remove from pan and immediately transfer to a large heatproof plate to finish cooling. Be careful, candied pecans are extremely hot. Set pecans aside to cool.
Preheat an outdoor grill for very high heat and lightly oil the grate.
Remove steak pieces from marinade, shake off excess marinade, and grill until steaks are seared and done to your desired degree of rareness, 1 1/2 to 3 minutes per side.
insert an instant-read meat thermometer inserted into the thickest part of a steak should read 145 degrees F (65 degrees C) for medium-well. Discard used marinade. Let steaks stand for 5 minutes after grilling before cutting into thin slices.