Cyclohexanol has a pKa = 16, while benzyl alcohol has a pKa = 15.4
The given explanation is that the "polarity of the benzyl group stabilizes the negative charge on oxygen".
My understanding is that when resonance is not a concern, benzyl groups are primarily electron donating by the inductive effect... which would destabilize charge on oxygen.
I know the inside of the aromatic ring is more negative, and the outside is more positive. Is it this positive charge that stabilizes the negative charge on oxygen?