Well, if you say that only converts who believe as Gerry believes are real converts, then by definition Gerry must be the most successful convert maker.
Since Gerry is in no obstinate denial of any doctrine or defined dogma of the Church, anyone who believes as Gerry believes is simply believing the Catholic faith.
But if you allow a wider definition of what constitutes a Catholic (perhaps the test might be: Would Benedict XVI consider this person to be a convert to the faith?), then Gerry can't be considered anywhere near the top of the list. The numbers just aren't there.
If by wider definition you mean one that allows error. Such as someone believing in Salvation outside the Catholic Church as Fr. Groeschel blatantly does, ( "I never bought into that" were his exact words.) then they and he are in denial of the Catholic faith (with Groeschel being the more culpable). Why not widen the definition of Catholics to include Protestants?
As far as Pope Benedict's opinion being the standard for considering someone truly in the fold, that would not be objective criteria. The standard would change according to the whims and orthodoxy of the Pope and liberal dissenters and heretics would not be able to be opposed on doctrinal facts.(think Pope Stephen on Pope Formosus).
Communion with the Pope and the Church is a one-way street. You are not in Communion with the Church because you protest that you are Catholic. You are in Communion by being in Communion with legitimate Pastors accepted by the Pope. "Communion ... is not understood as some kind of vague disposition, but as an organic reality which requires a juridical form and is animated by charity." (Vatican II, Lumen Gentium, Nota Previa)
To reject the ordination of all priests and bishops since 1968, and thus not hold communion with them, is to be at least in defacto schism, especially when one of them has been elected Pope.
Why do you need to distort the words of the Fathers on this doctrine? St. Cyprian and Origen and Lactantius and St. Augustine are clear enough that it refers to those who have left the bonds of the Church, not those who never heard the Gospel.