There are so many “destination” Madonna birthdays at this point, it’s difficult to keep track. There was Puglia when she turned fifty-nine, Marrakech when she turned sixty, Jamaica when she turned sixty-two. And who can really remember when it all even started to become such an event tailored for Instagram consumption? In the 80s and 90s, it seemed less about “going somewhere” for M than it was about dancing the night away. In any case, there was something about the “destination party” in Cuba the year she turned fifty-eight that felt particularly special. Maybe because it was at a moment in 2016 when the pendulum hadn’t quite swung all the way over to the side of “total shit.” After all, M’s birthday comes in August, just before a certain bleak election result would arrive in November of that year, changing the course of history irrevocably. But, three months prior, it was all sunshine, roses and “Hillary’s gonna win.” No one seemed to have a fucking clue what was coming, least of all “pinko liberal” Madonna. 

No, instead she was focused on being among the first of the celebrity cabal to take advantage of Obama loosening restrictions and allowing commercial flights between the U.S. and Cuba to occur for the first time in over fifty years. One imagines Kennedy would have been quite jealous of the achievement. And that he likely would not have made the cut for the guest list at M’s celebration that year.

From the moment, she deboarded her private jet, the red carpet was rolled out via the “True Blue”-esque vintage cars that were provided as a fleet to shepherd the reina and her crew into town. For the night of her fifty-eighth birthday in question, Madonna was filmed dancing on a table (she was doing that long before J. Lo—in addition to going to Italy in general, where Lopez seemed to now think she had jurisdictional supremacy). Being rich would make anyone engage in such behavior, after all. And, speaking of, let us not forget the lodging accommodations Madonna chose for her grand affair: the Saratoga Hotel. 

It was at this hotel, built in the 1930s and situated right across from El Capitolio, that M became involved in international subterfuge that was never reported to media outlets. For she was the perfect ruse to send to Cuba for Obama’s true purposes. No one would ever suspect Ms. Ciccone of anything—least of all a political scheme—as she had long ago normalized the act of traveling to exotic locales for her birth anniversary. This year, however, Obama was the one to bend her ear about going to Havana. And whatever Obama asked, Madonna would do, wishing, on some level, she could be Madonna Obama. If she absolutely had to get married again, that is. What he requested, this time (for there were other times as well), was that Madonna plant some bugs around strategic rooms in specific buildings she would be allowed access into in her role as Revered Celebrity. She was so high-profile as to be above suspicion, Obama reasoned. There were few people Madonna was willing to disappoint, and the first Black president was one of them. So she obliged. She didn’t even try to enlist the help of one of her many minions to do the deed. Madonna wanted to be able to tell Obama with a straight face that she completed the task all on her own. 

It began when she was invited for drinks with the president at El Capitolio. Something about the entire rendezvous harkened back, for M, to meeting with Carlos Menem in Argentina when she was filming Evita. Maybe she was just conflating Latin culture or maybe it was one too many mojitos sucked down right before arriving that made her experience this kind of déjà vu. The difference here, of course, was that, unlike in Argentina, she had to subtly start placing her bugs as opposed to pleading for use of the Casa Rosada. And wiretapping ain’t for the faint of heart or those who sweat easily (just ask Freddie Corso in Blow Out). Fortunately, being a guileful and flirtatious woman, this wasn’t as challenging as it would have been for others. In fact, there had been many moments in Madonna’s storied career when she had wanted to write a screenplay for Mata Hari’s biopic, sensing a kinship between her and this sex symbol. Alas, it was not to be, as she now had her own biopic to worry about. 

After spending what felt like hours with Raúl in his “special area” but what actually only amounted to thirty minutes, Madonna’s work was done. And it was work that didn’t come in handy in the long run (after all, look at the protest-laden shambles Cuba finds itself in today) for Obama’s political aims, but, at the very least, it made Madonna realize the extent of her capabilities. She now knew what Marilyn must have experienced with all that secret intel she had gathered from the White House. 

Upon finishing her spy work, Madonna got in one of the vintage blue Chevys with Debi and they proceeded to go on the prowl for young Latin boys just as they did on the Lower East Side during their early days. Madonna even thought of Carlos, the father of her favorite child, in that instant and she knew that her zest for all things Latin had only brought good into her life. How could anyone not be drawn to this culture? Socialist and dictatorial or not, it was so vibrant and alive. So dangerous and mysterious. All the qualities that Madonna herself wanted to exude. 

What ultimately felt so “special” about the Cuba birthday, she reckoned, was that it was the most invigorated M had ever been. Namely in her new role as “spy.” She wasn’t a Bond girl, but an Obama girl. On the plane ride back, the lines from that classic 80s track (a rare one that wasn’t her own) kept creeping into her mind: “all the boys think she’s a spy.” She liked the ring of that. The new enigmatic air it gave her that people couldn’t quite place. And she was certain it would, indeed, attract a lot of boys. Maybe even, someday, Barack. Until then, she would have to settle for “discreetly” channeling the incident into her eventual next record, Madame X, the promo for which overtly declares, “Madame X is a secret agent, traveling around the world.” And all under the guise of it being “for her birthday.”