Methods and apparatuses and systems for inserting advertisement segments into trick content. Advertisement segments present in the original video content are extracted from the video content and merged with other navigation segements to generate associated trick content. The advertisement segment may be inserted into the trick files may be displayed at their normal playback speed, a different apparent playback speed, or displayed in a different direction. Additionally, alternative content of the advertisement segment may be inserted into the advertisement segment to provide specialized versions of the advertisement content to be displayed in trick content mode, or the content may be completely different fro the original advertisement content, such as session specific advertisement content or even user specific advertisement content based on user preferences.