The Supersix would definitely fall into the "race" category...it's much more aggressive in geometry compared to the Synapse. You may also want to consider a Cervelo S1 or S2. They are "aero" road bikes and more geared towards triathlon and racing. Infact, the S-series come with a dual-position seat post that can be interchanged to a roadbike position or a tri position. Just something else to consider. The Madone comes in 3 fits - H1, H2, & H3. All of the stock WSD Madones come in the H3 fit, which is their most upright and relaxed fit. Most of the stock unisex Madones, are in the H2 fit...which is in the middle...not too racy, not too upright. I believe the H1 fit, which is their most racy and aggressive fit, is only available as a Project One build. So, unless you're planning on doing a Project One Madone, in which you can specify which fit you want...you will end up with either the H2 or H3 depending on if you go with WSD version or not. They explain the 3 different fits on the Trek website...worth a look if you want more info.