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Infuse the alcohol: Using the large holes of a box grater, grate 1 ½ lbs ounces ripe juicy tomatoes into a large bowl, discarding the leftover bits of flesh. Strain the pulp through a fine mesh sieve or strainer, to separate the pulp from the juice (save both!). Add the grated tomato pulp to a resealable jar, along with 8 ounces each gin and vodka (or if you are using only one liquor, a total of 16 ounces). Shake vigorously. Let infuse at least 3 hours and up to a week in the fridge. You can strain the pulp out at this point or keep it infusing for longer. If you want a totally pulp free martini, you’ll have to strain the pulp out before you start building the cocktail.
Make the tomato brine: In another container, or large measuring cup, stir together 1 cup of the strained tomato juice, ⅓ cup olive brine, ⅓ cup bread and butter pickle brine and ⅓ cup hot cherry pepper brine. Season the tomato brine mixture with a few big pinches of salt. Taste. If you want it spicier, more olivey or sweeter, adjust accordingly with the brines.
Stir ‘em up: Fill a cocktail shaker with ice. To make one martini: Add 2 ounces tomato infused alcohol, ¼ ounce dry vermouth, and 1 ½ ounces tomato brine to the shaker and stir very vigorously until very cold, at least 1 minute. Strain into a chilled martini glass and garnish with a cherry tomato.