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Rambling roses like your ‘American Pillar’ produce their flowers on laterals, the side stems that branch from the main canes.
As long as these main canes are growing straight up, they won’t produce many laterals, but you can encourage more side stems low down by training canes spirally around the upright supports.
Another possibility, if you have the space, is to fan the canes out at an angle; once they have produced enough side stems, you can move them back to a more vertical position.
The existing canes are probably too inflexible to retrain, but you can encourage new ones by cutting out a couple of the oldest canes right down at the base and amending the soil in early spring with a handful of ammonium sulphate (Epsom salts) dissolved in water. Follow up a couple of weeks later with some fish fertilizer or rose food.