Tolaini was founded in 1998 by Italian-Canadian entrepreneur Pierluigi Tolaini at Castelnuovo Berardenga, in the south-eastern corner of Chianti Classico. Legit is a single-varietal Cabernet Sauvignon drawn from selected estate parcels around the Montebello holding, where galestro and clay-limestone soils sit at moderate altitude. Under Lia Tolaini's leadership the estate has moved to a young team and increasingly organic, low-input farming. The wine takes its name and label from a tribute to jazz pianist Thelonious Monk. The 2018 growing season in Tuscany was cooler and wetter than the hot 2017, giving longer, more even ripening and a fresher, more classically structured style of red.

Hand-harvested Cabernet Sauvignon was destemmed and fermented in stainless steel under temperature control, with regular pump-overs to build colour and tannin. Following malolactic fermentation, the wine was matured for around twenty-four months in French oak barriques, a significant proportion of them new, before bottling. The extended elevage develops the cassis, graphite and cedar character and the firm, age-worthy tannic frame that defines Legit.