This looks comparable to other monthly wine subscriptions. For example, Bright Cellars' subscription was $80+S+H+tax for 4 bottles a month, with regular upsell emails for a 6-pack or 12-pack or a box of cheese.

It looks like American Airlines has had a partnership with Vinesse dating back to at least 2017: https://thepointsguy.com/2017/11/review-vinesse-wine-club-wo....

It looks like what's new is that they've slapped the Flagship brand on it, and given it a nice story to go with it.