Niccolò da Tolentino in the context of Andrea del Castagno

Andrea del Castagno (Italian: [anˈdrɛːa del kaˈstaɲɲo]) or Andrea di Bartolo di Bargilla (pronounced [anˈdrɛːa di ˈbartolo di barˈdʒilla]; c. 1419 – 19 August 1457) was an Italian Renaissance painter in Florence, influenced chiefly by Masaccio and Giotto di Bondone. His works include frescoes in Sant'Apollonia in Florence and the painted equestrian monument of Niccolò da Tolentino (1456) in Florence Cathedral. He in turn influenced the Ferrarese school of Cosmè Tura, Francesco del Cossa and Ercole de' Roberti.

The Battle of San Romano was fought on 1 June 1432, in San Romano, some 30 miles outside Florence, between the troops of Florence, commanded by Niccolò da Tolentino, and Siena, under Francesco Piccinino. The outcome is generally considered favourable to the Florentines, but in the Sienese chronicles it was considered a victory. As the 1430s began Florence had found itself in conflict with the rival city state of Lucca, and her allies, Siena and Milan.

The Florentine deployed about 4,000 horse and 2,000 infantry. The clash, which lasted for some six or seven hours, consisted of a series of heavy cavalry fights. It was decided by the intervention of a second cavalry corps commanded by Micheletto Attendolo.

The Funerary Monument (or Equestrian Monument) to Sir John Hawkwood is a fresco by Paolo Uccello, commemorating English condottiero John Hawkwood, commissioned in 1436 for Florence Cathedral. The fresco is an important example of art commemorating a soldier-for-hire who fought in the Italian peninsula and is a seminal work in the development of perspective.

The politics of the commissioning and recommissioning of the fresco have been analyzed and debated by historians. The fresco is often cited as a form of "Florentine propaganda" for its appropriation of a foreign soldier of fortune as a Florentine hero and for its implied promise to other condottieri of the potential rewards of serving Florence. The fresco has also been interpreted as a product of internal political competition between the Albizzi and Medici factions in Renaissance Florence, due to the latter's modification of the work's symbolism and iconography during its recommissioning.