Chelation-controlled aldol: why is the α substituent pseudo-axial?
Having the methyl group psuedo-axial means that when the nucleophile approaches, the transitiation state is chair-like. The energy penalty for having the methyl group initially in the less favourable position is compensated for the low energy TS. 

The ring-flipped version, in which the methyl group is psuedo-equatorial, would open via a high energy twisted TS (the opposite of the argument presented above, i.e. the low energy conformation of the starting material doesn't compensate for the high energy of the twisted TS).



Looking at the Evans' paper specifically, the TS he draws has an addition isopropyl group on the beta-carbon, which is equatorial (this would further stabilise the starting material, since the isopropyl would be far higher in energy if axial compared to the methyl).