I doubt it. Laffey has low name recognition and neither Democrat got 50% against him (one I recall was 44-29 with tons of undecideds). He's not actually conservative.
I don't know what platform exactly Webb is going to run on, but I'd be surprised if he got 40%.
Keep in mind that the Democrats also have low name recognition, so that argument means little. Also keep in mind that a primary battle between Chafee vs Laffery could pretty much turn into something along the lines of the independent republican who doesn't like Bush vs the [party line Bush Republican. their have been little shots hrere & there that Laffey has taken against Chafee regarding Chafee not being in tune with the Republican Party, and things along those lines. That is something which is only going to pick up and get more heated, which is something that is going to drive Rhode Island voters away from Laffey in droves (other than the hard party line Republicans which make a sup a small population of the state. In order for Chafee to defeat Chafee in the primary that is what he has to do. Position himself to the right of Chafee (which he is obviously) & try to point Chafee as being out of touch with the Republican Party. Problem with this is, it will help him in the Primaries, but bashing someone for not being a ture Republican and positioniing yourself as being more of a Republican than your opponent will destroy him in a state that is not only overwelmingly Democratic (5-2 margin or something along those lines) but has deep deated hatred of the sitting Republican Prsiden. Bush's #'s in Rhode Island are in the upper 20's with disapproval OVER 70%. positioning youself as being more of a Republican won't help in a General when the leader of the National republican Party is HATED by the state as a whole