One of my most memorable gaming experiences was the final choice in the Imperial Agent quest for Star Wars: The Old Republic. Not long being free of my “attachment” to World of Warcraft, I had decided not to play SWTOR. I didn’t want to get sucked into another MMO. But my husband bought it, and my resolve lasted for the thirty minutes I watched him play.
Even though I caved and bought the game and a six-month subscription, I never really got into the MMO part. While my friends were swinging their lightsabers around and apparently saving the galaxy I decided to explore the dark side. I chose the Imperial Agent story because it sounded interesting. Also, the voice actor for the IA sounded pretty sexy. I loved the story for all its twists and turns, but more so, I enjoyed the discovery that a universe famous for being black and white was really all shades of gray.
For those of you unfamiliar with the game, briefly, most of the major quests (and decisions) were a choice between dark and light. Your faction didn’t really matter, and this was one of the most fascination revelations. The Empire was full of people doing, um, people things. Living their lives. Doing good things. And the Republic was full of people doing not so nice things. Yes, the Empire was overrun with sith and the government wasn’t necessarily the, ah, best model. But to my delight, I found that my IA wasn’t necessarily a slave to that government. In fact, the way I played him, he developed into a man who was fiercely loyal his people, but able to question many of the things he had to do. He developed a streak of self-preservation, and if he could complete a quest without killing people, that’s what he did.
The result of this was interestingly realistic. I was able to play a character who felt genuine, but my inventory suffered because my IA had fallen neither to the side of dark or light. Because he walked a tightrope between these two extremes, I never got any of the cool gear allotted to these extremes. Though a little frustrating, this didn’t really bother me until I got to that last quest. True to form, BioWare had managed to surprise me. Things had been revealed. And I was sure that what I wanted—what my Imperial Agent and I would want—to do to square the game away would not be an option. There would be a dark choice and a light choice and either would be a compromise. It would be down to the one we could live with—maybe. If we were lucky.
There was a third choice and it was so perfectly tailored to what I wanted to happen, I sat there stunned. They’d been expecting the player like me. They’d been expecting the Imperial Agent who loved his job, loved his people, but who sometimes had to serve himself. It was an incredible moment, one I remember fondly, and one I remembered well last night when we got to the end of the last episode of Black Sails.

Black Sails held much of the same allure as choosing that Imperial Agent quest in SWTOR. A screen full of bad boys with sexy voices. I mean, who doesn’t love a pirate? And Charles Vane spent nearly all of the first two seasons shirtless.
I expected the show to be sympathetic toward pirates, and it was, but not universally. Pirates aren’t just a figment of our imagination—even if the story told by this series was a blend of myth, reality and clever plotting. This was not a long time ago in a galaxy far, far away. This was our history and pirate legends have never been black and white.
I think the biggest revelation for me was how so many of the characters fell into piracy. Only a handful conscious chose it. The rest were part of a crew or slid down the slope from privateer into piracy without ever really considering the difference. Many were outlaws, but a good number were… let’s call them conscientious objectors. And some of them were so f*cked over by the regime they’d given everything for, becoming a pirate was the only way to fight back.
Enter Captain Flint. Man, I loved this character. Every time I thought I knew who he was, they added another layer. It’s very, very difficult to write an utterly ruthless character that also possesses a core of decency—and make it work. They managed with James Flint. I’m not going to repeat his story here because I’d like to keep this post mostly spoiler free. That being said, it’s going to be difficult to talk about the final season and final episode without letting certain details slip.
I did not like Charles Vane (despite his wardrobe, or lack thereof), but over the course of two seasons, as I watched his and Flint’s stories move away from each other, curve back, cross, and move away in the opposite direction, only to repeat the process, curing back once more in an almighty clash, I came to respect him. As Blackbeard’s protégé, Vane was one of those men who rarely had a choice regarding the direction of his life. So when he did—have a choice, that is—he made it count. Wow, did he make it count.

I didn’t much care for Jack Rackham that first season, either. Anny Bonny scared the spit out of me. Billy Bones, I adored. He was the sort of character who always appealed to me: earnest and good and maybe a bit naïve. By the end of the series, the pendulum had swung on these three as well. Dark to light, light to dark, carving great grooves in the gray areas in between.
Long John Silver. I wanted to kill him throughout the first season. He was the most self-absorbed, self-centered, self… just full of self. His journey alone might have made the series worth watching, though. As a precursor to Treasure Island, Black Sails developed his story magnificently. But his developing friendship with Flint? The stuff of epic poetry. Seriously.

The bad guys in this series were, well, pretty much anyone who wasn’t a pirate or attached to Nassau in some manner. Here, again the writers continued to layer in the surprises. You’d have to be fairly naïve (like Billy used to be, d’aww) to believe that the British and Spanish fleets were full of good men who only sought to quell the pirate threat in the interest of guaranteeing safe shipping and thriving commerce between the colonies. I mean… really. Woodes Rogers was about a staircase beyond that. Dedicated and loyal, but not a very nice man. Like, not at all. Spoiler: he was probably the most brutal character in the entire story. I had to close my eyes more than once when he was on screen.
It was his character versus Flint and Silver that had me thinking back to my experience with SWTOR. I mean… if I pasted together a quick comparison, England was the Empire and the pirates were the rebels. Blood was shed on both sides. A lot of it. By the last season, we pretty much sat in stunned horror as the last desperate ploy on every side played out. You know those shows you want to binge? You finish one episode and roll right into the next? Not season four. One episode was enough. We needed time to check our blood pressure afterward.
Which brings me to the final episode—watched last night—and the point of this blog post. As we pushed play (with a trembling finger) and perched forward on the edges of our seats, I almost decided I didn’t want to go through with it. That I didn’t want to know what happened. I didn’t want to see characters I had come to care deeply for… die. I didn’t want the hearts of those awaiting the outcome of this final conflict to be broken. Hell, I didn’t want my heart to be broken. I’m not sure I’ve ever been so invested in a series finale. Like, ever.
And then it happened. That third choice popped up—the one put in there for people like me. For the folks who’d been cruising down the tightrope between dark and light, trying to do their best, failing a lot, but somehow keeping on doing, because there had to be a purpose to all of this. There had to be a reason and even if the reward came with a compromise, at the end of the day we could call it done.
The third choice, the unexpected epilogue for one character… I can’t tell you what it was. I can tell you it was amazing and beautiful and probably had me using twice as many tissues as any other conclusion might have. I couldn’t believe the writers had gone there. That they’d done it. But as I tottered up to bed, head aching from my tears, I thanked them for it. This isn’t to say the series had a totally happy ending. Let’s get real. This was about pirates and war. There were compromises. But I could live with them because of that one choice. That one amazing choice.
We’re surrounded by stories. I read a lot of books, I watch a lot of movies and TV. But it’s rare for me to leave a story feeling this emotionally spent. And over pirates. Those devilish and dastardly pirates. I spent four seasons heavily invested in the dark side and it’s going to be hard to come back from that.
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