While in Rome, Michelangelo kept up an active correspondence with Messer Lodovico, who, it appears, found himself in great financial straits at this time. Being a most dutiful and affectionate son, the young sculptor sent every available scudo of his money to succour his father and his three younger brothers, namely Buonarroto, born in 1477, whom he placed in the Arte della Seta; Giovan Simone, born in 1479, who led a vagabond life and was a source of continual trouble, and Sigismondo, born in 1481, who became a soldier. The letters which Michelangelo, in the midst of his artistic labours, found time to write home, full of tender solicitude and good advice and invariably containing a remittance, give us a touching insight into the beautiful and disinterested character which lay hidden underneath his stern and decidedly unattractive exterior.

He lived not only very economically, but penuriously, in order the better to help his family, and it appears that his health suffered not a little from these privations. His father heard of it, and wrote a letter, dated December 19th, 1500, in which these passages occur: "Economy is good, but above all do not be penurious; live moderately and do not stint yourself, and avoid hardships, because in your art, if you fall ill (which God forbid), you are a lost man. Above all things, never wash; have yourself rubbed down, but never wash!"

When Michelangelo returned to Florence in the spring of 1501, the fame of the great works which he had accomplished in Rome had already preceded him, and he was generally admitted to be the first sculptor of the day. Commissions came pouring in upon him, including one from Cardinal Francesco Piccolomini, who afterwards became Pope Pius III., for fifteen statues of saints to adorn the Piccolomini Chapel in the Duomo of Siena.

But he completely neglected this work in order to devote himself with characteristic ardour to a more congenial task, that of carving a colossal statue of David out of a huge block of marble which had been previously spoiled by an inferior artist and abandoned as useless in the Opera del Duomo. Surmounting the enormous technical difficulties which he had to contend with, Michelangelo succeeded, after nearly two years of hard work, in evolving from the crippled block of marble one of the greatest masterpieces of modern art.

On the 14th of May, 1504, Il Gigante, as it was called by the Florentines, left Michelangelo's workshop and was dragged with much difficulty to the Piazza della Signoria, where it stood until the year 1873, when it was removed to the hall of the Accademia delle Belle Arti. It has fortunately suffered very little from its exposure in the mild Florentine air, but the left arm was shattered by a stone during the tumults of 1527. The broken pieces were carefully collected, however, by Vasari and a young sculptor, Cecchino De' Rossi, who restored the arm in 1543. Another giant David in bronze was commissioned to Michelangelo in 1502 by the Republic, who wished to make a present of it to a French statesman, Florimond Robertet, but although this work is known to have remained for more than a hundred years in the château of Bury, near Blois, it has since disappeared.

While wrestling with the difficulties of his David, Michelangelo found time to accomplish many other important works, including two marble tondi in bas-relief, the first of which is now in the National Museum at Florence and the other in the Royal Academy, London. Both represent the Madonna and Child with the Infant St. John, and although lacking in finish they deserve to rank among the finest of Michelangelo's works. The composition is beautiful and simple, the modelling bold and the expression of the Madonna singularly noble and striking.

In April, 1503, Michelangelo was commissioned by the Operai of the Duomo to carve out of Carrara marble twelve colossal statues of the Apostles, one to be finished each year, and a workshop was specially built for the sculptor in the Borgo Pinti, but the contract could not be carried out, the unfinished St. Matthew, now in the courtyard of the Accademia, in Florence, being the only work which resulted from this commission: "And in order not altogether to give up painting," says Condivi, "he executed a round panel of Our Lady for Messer Agnolo Doni, a Florentine citizen, for which he received seventy ducats." This tondo, representing The Holy Family, with nude figures in the background, is now in the Uffizi Gallery, and apart from its originality and artistic merit, it is especially interesting as being the only easel picture which may be attributed with absolute certainty to Michelangelo.

In August, 1504, Michelangelo was commissioned by his friend and protector, Piero Soderini, Gonfaloniere of the Republic, to decorate a wall in the Sala del Gran Consiglio in the Palazzo Vecchio, a most flattering compliment to the young artist, as Leonardo da Vinci, then at the height of his fame, was already engaged in preparing cartoons for the opposite wall. Leonardo's designs represented the famous Fight for the Standard, an episode of the battle of Anghiari, fought in 1440, when the Florentines defeated Niccolò Piccinino. Michelangelo selected for his subject an episode in the war with Pisa, which gave him an opportunity to display his wonderful draughtsmanship and his profound knowledge of the human frame.

Benvenuto Cellini, who copied the cartoon in 1513, just before its mysterious disappearance, describes it as follows: "Michelangelo portrayed a number of foot soldiers who, the season being summer, had gone to bathe in the Arno. He drew them at the moment the alarm is sounded, and the men, all naked, rush to arms. So splendid is their action that nothing survives of ancient or of modern art which touches the same lofty point of excellence; and, as I have already said, the design of the great Leonardo was itself most admirably beautiful. These two cartoons stood, one in the Palace of the Medici, the other in the hall of the Pope. So long as they remained intact they were the school of the world. Though the divine Michelangelo in later life finished that great chapel of Pope Julius, he never rose halfway to the same pitch of power; his genius never afterwards attained to the force of those first studies."

Leonardo, after having begun painting a group of horsemen on the wall, abandoned the task with characteristic fickleness, and Michelangelo having been summoned to Rome in the beginning of 1505 by Pope Julius II., left his work unfinished. It is said that a worthless rival named Baccio Bandinelli, envious of Michelangelo's greatness, destroyed the famous cartoon of Pisa. A sketch of the whole composition may be seen in the Albertina Gallery at Vienna, but perhaps the most complete copy of the cartoon is the monochrome painting belonging to the Earl of Leicester, at Holkham Hall.