In the penultimate episode of The Handmaid’s Tale, Commander Joseph Lawrence made the ultimate sacrifice. However, Commander Nick Blaine was sure that he was on the “winning side.” The wording is something to pay attention to in this series.
Caution: This post contains SPOILERS for The Handmaid’s Tale season 6, episode 9
While there is a lot of focus on The Handmaid’s Tale season 6 finale, I want to go back an episode. After all, Nick’s death wasn’t focused on all that much in the series finale, and rightfully so. The focus had to be on June and Luke, figuring out what they do next and how the fight to take down Gilead for good continued.
Yet, Nick’s choice of words to Lawrence on the plane stand out in The Handmaid's Tale season 6, episode 9. As Nick joined the commanders to DC, he made a point about them being on the “winning side.” It wasn’t the “right side,” though, as many people would have said, making it clear that Nick really thought of Gilead.

Nick was always looking out for himself in The Handmaid’s Tale
Throughout the six seasons of the series, Nick was never really in the fight to bring down Gilead. In fact, he joined Gilead as an Eye, working as a driver for Commander Waterford, but spying on him at the same time. As time went on, he worked his way up the ranks, eventually becoming a Commander as well.
One thing always stood out, though. He would only help May Day and the fight against Gilead when the request came from June. Nick’s love for June made him want to fight for the “right” side, but in the end, he was always going to choose himself. As June went to Alaska, Nick decided against working with Tuello to bring Gilead down from the inside.
His decisions to go dark on Tuello made his intentions clear. He wanted to survive, and that meant choosing what he believed would be the “winning” side.

Nick knew that Gilead was the wrong side in The Handmaid’s Tale season 6
Despite all of this, deep down, Nick clearly knew that Gilead was wrong. He was one of those easily manipulated into the system, though. He came from nothing, and Gilead gave him the chance to rise up the ranks and create a life for himself. That chance just came with the choice of siding with people who would prevent women from reading and force women to breed.
Nick made it clear that he knew Gilead was wrong by not encouraging June to stay. He wanted to get June out, and he didn’t want her to bring their daughter back to Gilead. This wasn’t just out of love, but because he knew the life for Nichole/Holly wouldn’t be a good one.

If he really thought that Gilead was the right side, that’s the way he would have phrased things to Lawrence. Instead, he chose “winning,” and Gilead probably would have won against May Day had it not been for Lawrence deciding that he would rather sacrifice himself than allow the atrocities of Gilead to continue. What’s funny in Nick’s wording is that Lawrence did choose the “winning side,” but not the one Nick believed it would be.
No, I don’t believe Nick did make the choice to switch sides at the last minute. I believe by getting on that plane, he knew that he was dooming his soul to the Gilead cause. It wasn’t the right choice for all, but it was the choice he had to make for himself and his son. Nick was always a selfish character, and even his love for June couldn’t make him change that flaw in him in The Handmaid’s Tale.
The Handmaid’s Tale is available to stream on Hulu in full.