Grilled Pineapple Jerk Chicken Sandwich

I rarely take time away from work but when I do, I still find myself “working”. I love cooking for people, I always have. And that really is what drove me to be an entrepreneur - I wanted to be my own boss and cooking for people was the only thing I can do with confidence. 11 years later of refining my craft I’m always in my element when making sandwiches and cooking off the grill. This little timeout I’ve taken in Florida continues my daily sandwich making. For years people have been commenting on my photos always asking for the recipes for what I create. As I’m using this time in my career to shift gears and slow down a bit (in theory), there’s no better time to share all my creations for you to make at home off your BBQ. This week’s recipe is a Grilled Pineapple Jerk Chicken Sandwich that could easily beat Bobby Flay every day of the week ending in “Y”. Years ago, I was chatting with a very good friend who was born in Jamaica, and we were talking about Jerk chicken in detail. One thing he was adamant on was that slow burning wood was a necessary element to making proper jerk chicken - that an oven or a gas grill although close, couldn’t quite get it exactly where it needed to be. I’m so lucky because back in Toronto there is no shortage of incredible Jerk chicken spots on Eglinton West, best known for having huge drum bbqs out front of the shops grilling and smoking chicken.

The way you set up your bbq/smoker really contributes to the flavour of the chicken, and when it comes to this sandwich specifically, the perfect piece of slow, fire cooked chicken is the most important element of the jerk chicken sandwich. What’s super important about this process is building a solid fire with charcoal and wood to bring out that amazing natural flavour that pairs perfectly with the jerk spices. There are different ways to fire up your charcoal but my preference is to use a chimney and a fire starter cube. It takes about 20-30 minutes to heat up the charcoal this way, so make sure to get that going before you intend to start cooking. I like to add wood chips or chunks on top of the coal to get a nice smoky flavour. My go-to is usually any fruit-based wood so for this recipe I used cherry wood. We’ll also be cooking our jerk chicken on indirect heat so those chicken thighs will remain tender when fully cooked and almost fall apart when it’s done. The final step in making your jerk chicken is getting it on the hot side of the grill to get some grill marks and caramelization of the sugars in your jerk sauce.

Jerk chicken is traditionally a low and slow recipe, you can use whole chicken, or chicken wings, but for this recipe I’m using skin-on, boneless chicken thighs because they are going to be used in my very epic Jerk Chicken Sandwich. I’m going to make the Jerk sauce from scratch using fresh ginger, garlic, green onions and scotch bonnet peppers to add that heat that is typical of jerk sauce. I like spice so I’m going to use three scotch bonnet peppers in my sauce, but feel free to adjust that number based on your spice tolerance. If you want to use one, use one, I won’t judge. I then used a combination of dried spices that are typical to jerk sauce like cinnamon and allspice, soy sauce for a nice umami flavour and some honey and brown sugar to sweeten it up. I’ve also incorporated two ingredients to my jerk sauce that make it less traditional but both really do add to the flavour quite nicely. I use ginger beer as my liquid instead of just water; the tartness matches perfectly with the fresh ginger flavour that already exists. The other being the grilled pineapple - it’s sweetness, juiciness, caramelized intensity and acidity are an absolute no-brainer addition to this already stellar recipe.

Like any great sandwich, this one has just a few ingredients but each one is thoughtfully done and when put together makes for one very epic sandwich. The spice and smoky flavour from the jerk chicken, paired with a creamy, crunchy and cool cabbage coleslaw, lettuce for garnish and a soft and buttery brioche bun create the perfect bite. Keep reading to find out how you can make your own Grilled Pineapple Jerk Chicken Sandwich or click here to jump to the full recipe.

The first step is to get your charcoal going. Give yourself about 20-30 minutes for the charcoals to get hot, once they are white, you know they're ready to go. Like I mentioned, I like to use a chimney and a fire starter cube, but if you have a different method, all good. Once the hot coals are placed in the bbq, I layer some cherry wood on top to get that great smoky flavour going.

We're going to make our jerk sauce from scratch, so I like to gather all my fresh ingredients, like garlic, ginger, green onions, fresh thyme and scotch bonnet peppers. You're going to add all of these ingredients to a container and then squeeze in the fresh lemon juice, add in soy sauce and ginger beer and then blend until smooth.

Next up are adding in your dry spices like cinnamon, onion powder, dried thyme and allspice - what gives jerk sauce its characteristic colouring. Then we'll add some honey and brown sugar and blend again.

What makes this jerk sauce extra special and little different is the addition of grilled pineapple. Cut your pineapple into rounds, I used two large ones, and put them on the hot bbq for a couple of minutes on each side, until they are nicely caramelized but not over-cooked. Once done, remove from the grill, cut off the skin and remove the core, cut into chunks and add to your jerk sauce and blend until smooth.

Once the jerk sauce is finished, you want to marinate the chicken. First start by salting each side of your skin-on, bone-in chicken thighs and then cover with your jerk sauce. Keep some of the sauce to baste your chicken while it cooks, and to add to your coleslaw. Ideally you can leave your chicken to marinate over night, covered, or at least a couple of hours if you don't have that kind of time. Once your chicken is done marinating, you're going to place them on the bbq on indirect heat, away from the charcoal, and let it cook for 30-45 minutes. Don't forget to baste the chicken with the extra jerk sauce while it cooks. After the chicken is done, move onto the hot side of the grill and let it caramelize for a couple of minutes on each side over the heat, basting again with sauce as you go.

While the chicken is cooking, it's time to make a nice cool and crunchy coleslaw. It's super simple, just some chopped green cabbage, shredded onions, salt, mayo and a bit of that reserved jerk sauce.

To build your sandwich, place your brioche bun on the bbq to get slightly toasted, put down two pieces of lettuce on your bottom bun, top with the jerk chicken and coleslaw, close the bun and dig in. I made a monster of a sandwich with three chicken thighs, but feel free to either make four smaller sandwiches with one thigh each, or two bigger sandwiches with two thighs piled on. Or, you can go nuts and do three pieces of chicken like I did.

And now for the full recipe...

Grilled Pineapple Jerk Chicken Sandwich

Makes 2-4 sandwiches (serves 2 to 4 people)

Prep Time: 30 minutes

Marinating Time: 12-24 hours (optional)

Cook Time: 30-45 minutes

Total Time: 1-1.5 hours + 1 Day

Ingredients

4 Skin-on boneless chicken thighs

Salt

For the jerk sauce:

3 scotch bonnet peppers

¼ cup fresh ginger

8 cloves of garlic

2 stalks green onions

1-2 sprigs fresh thyme

1 lemon

2 tbsps soy sauce

½ cup ginger beer or water

1 tsp cinnamon

½ cup of allspice

1 tbsp onion powder

1 tbsp dried thyme

2 tbsp honey

1/4 cup brown sugar

1 pineapple

Coleslaw:

½ green cabbage

1 cup shredded carrots

3 tbsps mayo

1 tbsp jerk sauce (optional)

Salt

To build:

2-4 Brioche buns

8 Boston lettuce leaves

Equipment:

Immersion hand blender

How to Make it:

Before getting started, you have to build your fire. The first step is to use a chimney to get your charcoal hot. I like to buy fire starter cubes, set them on the grill, light them, fill up my chimney with charcoal and then set it over the starter. Once the charcoal has turned white, you know it is raging hot. Pick up the grill and pour your hot charcoal into the bbq, and then add your wood right on top of the coals. It will create a lot of smoke and that’s how you’ll know it’s hot and ready.

In a tall container (I used the one that comes with my hand-blender) add in the scotch bonnet peppers first; you can use as many as you like, depending on your spice tolerance, I used all three. Then add all the garlic, roughly chop the green onions, removing the green tops and add them into your container. Remove the thymes leaves off the stem and add to your container. Add juice from one lemon. Peel your ginger and roughly chop and then add to your container. Add in the soy sauce, the ginger beer or water, and blend with an immersion hand blender until combined.

Now it’s time to add the dry spices and sugars to the wet ingredients. Add in the cinnamon, allspice, onion powder, dried thyme, honey and brown sugar. Blend until smooth.

While you wait for your bbq to come up to temperature, you’re going to prepare the pineapple. This isn’t a traditional step, but it adds a great sweetness to the sauce. Slice your pineapple into large rounds, with the skin on, and then place directly over the charcoal on the grill. Cook for a few minutes on each side, so it is nicely caramelized and not overly cooked. Take off the grill and remove the core and skin, cut into cubes and then blend into your marinade. You can do this in steps, adding the pineapple and then blending and adding in more, or make sure to blend at different levels to smooth out any chunks.

To prepare the chicken, place your skin-on, boneless thighs on a plate, and generously salt on each side. Pour the jerk marinade over the chicken and completely cover all sides. Make sure to reserve some extra sauce for basting your chicken while it cooks and to add a little into your coleslaw. Ideally, you are marinading the chicken in a covered bowl in the fridge overnight to give it the proper chance to marinate. If you don’t have the time, even a couple of hours - heck thirty minutes - to marinate, would be helpful.

Once your bbq hits about 350F, it is ready to go for your chicken. Put your chicken on the grill, over indirect heat, on the other side of the grill away from the charcoal and wood. Spoon or brush some additional jerk marinade on the top of the chicken and let it cook for about 30-45 minutes. Once the chicken is done cooking on the indirect heat, you are going to move it over to direct heat to get some nice grill marks and help to caramelize the sugars in the marinade. Be careful while moving the chicken over since it will be very tender from cooking over the indirect heat and may easily fall apart. Baste with a little more jerk sauce, and then once nicely charred on each side, remove from the bbq.

While the chicken is finishing, you’re going to make a coleslaw for your sandwich. Take half your cabbage, and cut it in half again. Working with just a quarter of the cabbage at a time, finely chop it into thin strips. Put the cabbage in a bowl and add in the shredded carrots, lightly salt and toss together. Add in your mayo and drizzle in a bit of the pineapple jerk sauce (optional) and mix all together.

To build your sandwich, start by placing your bun on indirect heat on the bbq to get a bit toasted. Once off the grill, place a couple of pieces of lettuce on the bottom of the bun, add 1-2 pieces of chicken, top with the coleslaw and top bun. Dig in!

Make sure to subscribe to my newsletter so you never miss out on a new recipe, follow me on all my social channels @chefmattbasile and check out my YouTube Channel for the full step-by-step recipe video.