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Why doesn't my font work?

I'm using BookWright and I'm having font issues. I wanted to use a condensed version of a font I already own, but BookWright doesn't recognize the variations (regular/condensed/oblique/bold). So I spent $90 on an OpenType version of the font I want to use, and while BookWright recognizes it, it looks terrible (see attached). Why? 

Screen Shot 2015-11-21 at 10.34.44 PM.png

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