First I will not be able to give you a fully satisfactory answer, since the issue is not resolved. The mass-gap problem is a well-defined mathematical problem whose solution is worth $1M (Clay millennium problem).
Physically we have some hindsights. First, the vacuum inside hadrons is not the same as the vacuum outside. From this point you can understand why all this is related to confinement. Now in the vacuum inside hadron, you can picture valence quark propagating as constantly exchanging gluons between the other valence quarks. A gluon is pretty similar to, and willing to fluctuate into, a pair quark-antiquark. All those gluons and quark-antiquark pairs are virtual. So you may picture a naked valence quark with mass of a few MeV in the vacuum inside hadrons really as dressing into a constituent quark with mass around 300 MeV. This crazy claim is supported by more rigorous Dyson-Schwinger method to calculate the quark propagator (among other model calculations). I don't remember what chiral symmetry breaking has to say about "constituent mass" however.