Psalms 17, 36, 57, 61, and 91 portray people seeking refuge under the LORD's wings; Israel's history also repeatedly features God sending rejected prophets.
The temporal force of 'how often' is striking because Jesus speaks as the would-be gatherer of Jerusalem across its pattern of resistance.
The saying strongly suggests Jesus occupying the divine gathering role. We discuss its pre-existence implication without assigning the stronger 'Claims Eternal Existence' prerogative, since Jesus does not explicitly state pre-human existence here.
Jerusalem is characterized as unwilling to be gathered.