Ironwood was originally Winter's superior in the Atlesian Military. Originally, she held a great deal of respect for Ironwood and would always follow his orders without question. Ironwood also reciprocated this sentiment, as when he argued with Jacques Schnee he told him that Winter was one of his best soldiers. We first see the two together in volume 3 when he scolds Winter for getting into a fight with Qrow Branwen. He then later dismisses her from the room to talk with Qrow, Glynda and Ozpin alone.
In the beginning of volume 8, it was revealed that Ironwood had chosen Winter to be the next Winter Maiden. He also told her the truth about Salem and the Relics. In chapter 8, Ironwood and Winter were shown joking about smiling for the cameras. To which Winter tells him that he would have to pay her. She then later defends him against the verbal attacks against Jacques Schnee.
In volume 7 chapter 11, after Ruby's warns about Ironwood's plan, Winter seems shocked and disturbed about what she hears, but with that being said, she was still willing to follow through with Ironwood's plans to kill Fria and harness the Winter Maiden powers. This shocks and angers Penny, with her asking if this bothers Winter at all. This perplexes Winter, but she defends Ironwoods actions saying that he is making hard choices so that they don't have to. For the many not the few.
In "The Enemy of Trust", after going to the vault and hearing someone going down the elevator, Ironwood with his back turned thinking it was Winter apologized to her and told her he knew that could not have been easy. Shortly then after Penny became the winter maiden, Winter still refused to betray Ironwood. However Winter still "suggested" that Weiss and her friends leave, telling them she was giving them a head start. In volume 8 chapter 1, Ironwood visits Winter and tells her that she was glad that she was alright. He then confesses to her that he wouldn't know what he would do without her support. Winter at first seemed happy and relieved, but then became shocked when he killed Councilman Sleet right in front of her when he protested against Ironwood's decision to declare martial law.
In chapter 10, when Winter's team comes back, he heaps praise upon her thinking they had blown up the whale. When Winter tells him that it wasn't them and that they still had the bomb, he then puts a reassuring hand on her shoulder and tells her of his plan to hold Mantle hostage. This visibly disturbs Winter. Her relationship with him then becomes strained when Harriet tells him that Winter let Yang's Group go to rescue Oscar instead of keeping them arrested. This visibly angers Ironwood to the point where he smashes his table out of rage. Winter then decides to betray Ironwood when he almost kills Marrow for speaking out against him.
In chapter 12, she defeats him along with Oscar and Team JNPR and then imprisons him in a cell next to her father. In chapter 13, Winter is confronted by Ironwood at the Vault with a weapon harnessing Penny's maiden powers, where he demands she step aside. Winter refuses and tells him that she has always defended Atlas against all of it's enemies. She then draws her swords against him. Ironwood then sheds a single tear out of his one real eye and prepares to fight against her by running towards her.
In the final episode, Winter rejects Ironwood's attempts at trying to resolve the fight peacefully. She also displays her anger fully when fighting him. Once Winter acquires the Winter Maiden powers, she is then easily able to defeat Ironwood by deflecting one of his attacks against him. She then leaves him for dead.
Winter Soldier is a rare pair within the RWBY fandom. Some people think of them having more of an father-daughter relationship since Winter has a strained relationship with her own father. Some fans have also jokingly said that Winter might like older men. The two have been compared to Hawkeye and Mustang from the Full Metal Alchemist series. It has a small fanbase on Tumblr.
- "Winter Soldier" comes from Winter's name and the fact that Ironwood is a soldier.