Lorenzo's grandfather, Cosimo de' Medici, was the first member of the Medici family to lead the Republic of Florence and run the Medici Bank simultaneously. As one of the wealthiest men in Europe, Cosimo spent a very large portion of his fortune on government and philanthropy, for example as a patron of the arts and financier of public works. Lorenzo's father, Piero di Cosimo de' Medici, was equally at the centre of Florentine civic life, chiefly as an art patron and collector, while Lorenzo's uncle, Giovanni di Cosimo de' Medici, took care of the family's business interests. Lorenzo's mother, Lucrezia Tornabuoni, was a writer of sonnets and a friend to poets and philosophers of the Medici Academy. She became her son's advisor after the deaths of his father and uncle.
Lorenzo, considered the most promising of the five children of Piero and Lucrezia, was tutored by a diplomat and bishop, Gentile de' Becchi, and the humanist philosopher Marsilio Ficino, and he was trained in Greek by John Argyropoulos. With his brother Giuliano, he participated in jousting, hawking, hunting, and horse breeding for the Palio, a horse race in Siena. In 1469, aged 19, he won first prize in a jousting tournament sponsored by the Medici. The joust was the subject of a poem written by Luigi Pulci. Niccolò Machiavelli also wrote of the occasion, perhaps sarcastically, that he won "not by way of favour, but by his own valour and skill in arms". He carried a banner painted by Verrocchio, and his horse was named Morello di Vento.
Piero sent Lorenzo on many important diplomatic missions when he was still a youth, including trips to Rome to meet the pope and other important religious and political figures.
Lorenzo was described as rather plain of appearance and of average height, having a broad frame and short legs, dark hair and eyes, a squashed nose, short-sighted eyes and a harsh voice. Giuliano, on the other hand, was regarded as handsome and a "golden boy", and was used as a model by Botticelli in his painting of Mars and Venus. Even Lorenzo's close friend Niccolo Valori described him as homely, saying, "nature had been a stepmother to him in regards to his personal appearance, although she had acted as a loving mother in all things concocted with the mind. His complexion was dark, and although his face was not handsome it was so full of dignity as to compel respect."
The Adoration of the Magi
includes several generations of the Medici family and their retainers. Sixteen-year-old Lorenzo is to the left, with his horse, prior to his departure on a diplomatic mission to Milan