Get the Recipe
When life gives you lemons, you make lemonade. When Past You gives Present You leftover Cuban roast pork, first you drink a toast to Past You for the generosity and forethought (a mojito is both thematically and gustatorily appropriate), then you pay it forward by making a Cubano sandwich for Future You.
Don't worry: Once you have that pork (thanks, Past Me, for doing all the hard work!), the rest of the sandwich is exceedingly simple to make. It's not much more than a gussied-up ham and cheese toastie, though saying that discredits it. It's more than just another ham and cheese. It is the unchallenged champion of ham and cheese sandwiches. El rey de jamón y queso. El tigre numero uno. A ham and cheese sandwich so far elevated by pickles, roast pork, and mustard that it almost transcends the genre.
Some folks claim that the sandwich originated in Cuba and eventually made its way to the States, but from my reading, it seems far more likely that the Cuban mixto sandwich emerged in the mid-19th century to feed cigar- and sugar-factory workers in Key West, Ybor City, and Tampa. As Tom Scherberger reports for Florida's tourism board, records of Cuban sandwiches go back to well before Miami even registered on the map as a real city, though it's less clear when toasting the sandwiches in a press—to my mind, an essential part of what makes a Cubano a Cubano—became the norm. Perhaps Miami may have some claim to that particular innovation?
As with the cassoulet of southern France, a dish with equally contentious origin-story rivalries, I find it best to just observe these feuds from afar, enjoying the delicious fallout of the debates rather than taking sides.
The easy part is collecting the extra ingredients. I use honey ham sliced from the deli (any sort of sweet ham will do—you want that sweetness to contrast with the savory roasted pork), along with deli Swiss cheese slices and dill pickles, which I slice by hand very thinly lengthwise. This is a case in which hand-slicing will give you superior results to the typically-too-thick-for-a-Cubano slices that you get in jars. You want that pickle to really meld with the other ingredients.
For the bread, ideally you want to get a real Cuban loaf. The bread is typically a white, European-style long loaf made with a good amount of lard added to the dough, which gives it a subtle flavor and a distinct softness, allowing it to crisp up nicely without getting so hard that it rips up your gums as you bite into it. Your best bet is to look for a local Latin bakery. Even if they don't specifically make Cuban bread, I've found that most Mexican, Puerto Rican, and Dominican bakeries will have something similar. If all you've got is a standard North American supermarket, so-called soft "French" or "Italian" bread or a not-too-crusty ciabatta is the way to go. Skip fancy artisan baguettes and the like—they'll be too tough.
To construct my sandwich, I start by spreading a moistening layer of mustard over each bread half. Next, I layer the halves with cheese. It's important to have cheese on both sides—it is the mortar that holds the sandwich together.
Here's where the real Tampa-versus-Miami debate occurs. See, aside from Cuban immigrants, Tampa was also home to many Italian immigrants, and as the two cultures met, so did their foods. Eventually, Genoa-style salami became a staple ingredient in Tampa-style Cubanos. Folks on Twitter were quite rambunctious when I asked about the legitimacy of salami on a Cuban sandwich, with 34% declaring "no way!" (my guess: all Miami residents and visitors) and 54% saying that it "sounds weird but I dig it." Presumably the 12% of people who voted "of course" are from Tampa.
Ah, the tyranny of the masses in action.
I won't force your hand either way, but personally, having tried both side by side, I gotta go with Tampa on this one. Cubanos made with salami are downright delicious, with the salami adding a little funk to the sweet-savory pork situation. Either way, when you're done layering give he sandwiches a gentle press with your hand to make sure that nothing is gonna slip or slide when you get to the real pressing.
To press the sandwich, there are a couple of options. If you have a panini press with either flat or ridged plates, by all means break it out and use it, after greasing it with butter, of course. (And don't take any guff from someone who tells you that a Cuban sandwich must be pressed on a flat plancha, not a ridged panini press. The ridges make it extra crispy and delicious, despite its inauthenticity.)
I've used this inexpensive Hamilton Beach sandwich maker for nearly a decade now, with good results. At the Serious Eats office, we have a Cuisinart Griddler, which, while pricier, offers both flat and ridged plates to work with. Both are convenient if you make a lot of hot sandwiches, but for most folks, they'll wind up taking up shelf space most of the time.
If you don't have a press, just form a makeshift one with a couple of hot surfaces. I'm using my Mini Baking Steel Griddle here, along with a cast iron pan to weigh the sandwich down (you'll have to flip the sandwich halfway through cooking). But two cast iron pans works fine, as does a stainless steel pan, a Teflon pan—heck, even a waffle iron or a clothes iron can double as a sandwich-toasting implement.*
* Pro tip: Going on a staycation? Construct Cubanos, butter lightly on the exterior, then wrap them in aluminum foil. When you get to your hotel, iron those sandwiches for about seven minutes on each side, unwrap, and enjoy your hot, crispy sandwich. This is the reason I used to keep an iron in my desk drawer during the short period of my life in which I had an office job.
Pushing quite hard is key here. The bread should compress down to about a third of its original volume, and all of the internal ingredients should meld. Just don't push so hard that mustard and juices squeeze out and make the bread soggy.
I hope you bought an extra-long loaf, because these sandwiches ain't gonna stop until the pork runs out.**
** "Ain't Gonna Stop Till the Pork Runs Out" is, coincidentally, the title of the fourth track of the album of kids' songs I'm working on. We started with the title and are building the song around it.