Cuban Sandwich Quesadillas: The Ultimate Game Day Fusion for Flavorful Tailgating
Get ready to elevate your game day experience with a sensational dish that marries two beloved culinary classics: the savory, tangy notes of a traditional Cuban sandwich with the cheesy, crispy perfection of a quesadilla. This innovative Cuban Sandwich Quesadilla offers the best of both worlds, transforming a well-loved sandwich into an irresistible, easy-to-eat appetizer or main course that’s perfect for any football party with friends, family, or fellow fans. Prepare for a flavor explosion that will have everyone asking for more!
With football season just around the corner, anticipation builds not only for thrilling plays and nail-biting finishes but also for the incredible food that accompanies every tailgate and home viewing party. This year, I’ve teamed up with 63 other passionate foodies, bringing you a grand total of 64 mouth-watering, tailgating-worthy recipes! It’s an epic culinary lineup designed to make your football season gatherings unforgettable, and my contribution is a true crowd-pleaser.
Fact: I absolutely adore football season, even if I don’t always grasp every intricate detail of the sport itself. What truly captivates me are the traditions surrounding it: the frequent get-togethers with friends, the welcome (if slight) cooling of the weather here in sunny Florida, and, of course, the glorious FOOD! For today’s special link-up, each major city boasting a football team has two dedicated food bloggers representing their team’s culinary spirit. Being based in Tampa, it’s no secret which vibrant city and team I’m proudly representing!
Our city is home to Raymond James Stadium, an iconic venue where both USF (my husband Jason’s alma mater) and the legendary Tampa Bay Buccaneers play. Strategically located near several of Tampa Bay’s most celebrated Cuban restaurants, the stadium provides the perfect backdrop for my culinary inspiration. Given this rich local heritage, I knew without a doubt that today’s recipe simply had to pay homage to the king of Tampa sandwiches: the iconic Cuban Sandwich!
It’s hard to imagine, but I had never experienced the excitement of a live football game until I met Jason. In the early days of our relationship, he lived conveniently within walking distance of Raymond James Stadium, which was truly amazing! We’d pack a cooler full of drinks and snacks, then embark on a leisurely stroll to meet up with friends, soaking in the pre-game atmosphere. After the game, our tradition often involved stopping at a beloved local Cuban restaurant on the way home to grab a classic Cuban sandwich to split. These moments, filled with camaraderie and delicious food, forged a deep appreciation for the culinary traditions of Tampa.
The Inspiration: From Classic Sandwich to Crispy Quesadilla
While I cherish those memories of enjoying authentic Cuban sandwiches, recreating the exact magic of a professional Cuban sandwich at home, with its perfectly pressed bread and precise ratios, can be a challenge. But why limit ourselves to tradition when we can innovate? Instead of a direct replication, I envisioned a new format that would capture all the iconic flavors while adding an exciting, party-friendly twist: the Cuban Sandwich Quesadilla.
This fusion dish allows me to blend the best elements of a classic Cuban sandwich – the savory mojo pork, thinly sliced ham, tangy pickles, and melty Swiss cheese – with the comforting, crispy embrace of a quesadilla. And to truly kick it up a notch, I paired it with my sensational Mustard Aioli. This homemade aioli isn’t just a condiment; it’s a game-changer, adding a creamy, zesty depth that perfectly complements the rich and savory fillings. It’s truly the perfect football food – easy to hold, satisfyingly crunchy, and bursting with flavor!
Mastering the Mojo Pork: Slow Cooker vs. Oven Methods
The heart and soul of any great Cuban sandwich, and by extension, this quesadilla, is the flavorful mojo pork. The beauty of this recipe is that once you’ve prepared the succulent mojo pork, assembling the quesadillas themselves is incredibly simple. I’ve made this fantastic pork before using two different methods, both yielding delicious results:
- Oven Method: Previously, I prepared the pork in the oven, which is excellent for achieving those tasty charred, crispy edges that add an extra layer of texture and caramelized flavor. This method requires a bit more active attention but rewards you with deeply browned bits that are absolutely scrumptious.
- Slow Cooker Method: For today’s recipe, I opted for the slow cooker. This hands-off approach makes the process incredibly convenient. You simply set it and pretty much forget about it for a few hours, allowing the pork to slowly braise in the aromatic mojo marinade until it’s fork-tender and incredibly juicy. The slow cooker produces a moist, succulent pork that shreds effortlessly, making it ideal for filling quesadillas. It was just as good, and the convenience was a definite bonus!
Whether you prefer the crispy bits from the oven or the set-it-and-forget-it ease of a slow cooker, the key is the vibrant mojo marinade. This blend of citrus juices (orange, lime, lemon), olive oil, garlic, onion, oregano, and cumin infuses the pork with an unparalleled zesty and savory flavor that is utterly essential to the Cuban experience. Choose whichever cooking method suits your schedule and preference; the delicious outcome is guaranteed.
Every bite of this quesadilla is a delightful symphony of textures and flavors. It’s incredibly crunchy on the outside, with perfectly melted cheese and tender, flavorful fillings on the inside. It truly tastes like my favorite Tampa sammie, but in an exciting, innovative quesadilla format. The addition of the Mustard Aioli isn’t just an option; it’s a necessity. This creamy, tangy condiment elevates the entire dish, providing a rich, zesty counterpoint to the savory pork and ham. Seriously, this mustard aioli is life, you guys!
These Cuban Sandwich Quesadillas are not just for game day. They make an amazing quick weeknight dinner, a fun lunch, or a spectacular appetizer for any gathering. The combination of succulent mojo pork, savory ham, gooey Swiss cheese, and zesty pickles, all encased in a perfectly crispy tortilla and dipped in that incredible mustard aioli, creates a culinary experience that’s truly unforgettable. It’s a bold, flavorful twist on a classic that you’ll want to make again and again.
Cuban Sandwich Quesadillas
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Ingredients
Cuban Pork
- ½ cup olive oil
- ½ cup orange juice – fresh-squeezed or I like this brand
- ¼ cup fresh-squeezed lime juice
- ¼ cup fresh-squeezed lemon juice
- ½ cup chopped onion
- 10 garlic cloves
- 2 tablespoons dried oregano
- 2 teaspoons ground cumin
- 1 teaspoon Kosher salt
- 1 teaspoon pepper
- 3 pound pork butt
Mustard Aioli
- 2 tablespoons Dijon mustard
- 1 egg yolk
- 1 tablespoon fresh lemon juice
- ½ cup olive oil
- 3 tablespoons stone ground mustard
Quesadilla
- 4 tortillas
- 4 slices Swiss cheese
- 4 slices baked deli ham
- 4 tablespoons mustard aioli – recipe above
- pickle slices
Instructions
Cuban Pork
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Place all ingredients for the Cuban Pork marinade (olive oil, orange juice, lime juice, lemon juice, chopped onion, garlic cloves, dried oregano, ground cumin, Kosher salt, and pepper) into a blender. Blend on high until smooth to create the aromatic marinade.
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Pour the prepared marinade into a large plastic zip-top bag or a shallow container.
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Using a sharp pairing knife, pierce the pork butt deeply on all sides. This helps the marinade penetrate the meat thoroughly. Add the pork to the container with the marinade and seal it tightly.
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Marinate the pork in the refrigerator for at least 4 hours, or for optimal flavor, overnight (up to 24 hours).
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Transfer the marinated pork (along with the marinade) to a slow cooker. Cook on low heat for 6-8 hours. Begin checking for tenderness around the 6-hour mark; the pork should be easily shreddable with a fork.
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Once cooked, remove the pork from the slow cooker and use two forks to shred it into tender, succulent pieces. Discard any excess fat.
Mustard Aioli
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In a mixing bowl, combine the Dijon mustard, egg yolk, and fresh lemon juice. Whisk vigorously until the mixture is smooth and well combined.
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While continuously whisking, slowly drizzle the olive oil into the mustard mixture in a thin, steady stream. Continue whisking small amounts of oil in at a time until it is completely emulsified and incorporated. Keep whisking vigorously until the aioli becomes thick, creamy, and pale yellow. Stir in the stone ground mustard for added texture and flavor.
Quesadilla Assembly
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Heat a nonstick skillet over medium heat. Lay one tortilla flat in the skillet. On one half of the tortilla, spread approximately 1 tablespoon of the prepared mustard aioli. Layer with a slice of baked deli ham, a slice of Swiss cheese, and 1-2 tablespoons of the shredded Cuban pork. Add a few pickle slices over the pork.
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Cook for 4-5 minutes, or until the bottom of the tortilla is golden brown and crispy, and the Swiss cheese has fully melted and become gooey.
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Carefully fold the empty half of the tortilla over the toppings side, creating a half-moon shape. Gently flatten the quesadilla with a spatula to ensure even heating and crisping.
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Flip the quesadilla and cook for another 2-3 minutes on the second side, until it’s also golden brown and crispy, and the fillings are piping hot.
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Remove the finished quesadilla from the heat and transfer it to a cutting board. Allow it to cool for a minute before cutting it into wedges or strips for easy serving.
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Serve immediately, dipping into extra mustard aioli for an added burst of flavor, if desired. Enjoy your homemade Cuban Sandwich Quesadillas!