When Rubin brothers Alec and Bradley decided to follow in their father’s footsteps and start making cigars of their own, we were admittedly a little skeptical. But here we are with the Alec & Bradley Gatekeeper Robusto making an auspicious appearance on our list at No. 7—not too bad for a couple of blending rookies. Then again, they did get a little help from industry veteran Ernesto Perez-Carrillo who makes the cigar in the Dominican Republic. Ultimately, the Gatekeeper is a collaboration between Perez-Carrillo and the young Rubins. The project gave Alec and Bradley the opportunity to not only learn from Perez-Carrillo, but to gain some experience with Dominican tobacco. “We are a part of the next generation of the premium cigar business,” says Bradley, “and Ernesto is a legend.” The Gatekeeper finds synergy and balance with its backbone of pepper (both red and black), nougat and caramel that’s spicy in the right places, sweet in the right places and pops with savory snaps of leather. The band depicts the mythical head of Medusa, which is part of the famous bronze statue Perseus With the Head of Medusa by Benvenuto Cellini. We’re not exactly sure how that ties into the cigar or the story behind it, but we know that this collaboration points to an encouraging future in the business for the brothers Rubin.