However, like all art from the Italian Renaissance period this date is only an estimate. The 44.5 cm × 34.5 cm (17.5 in × 13.6 in) painting is said to be based off of the medals executed in 1445 and 1450 of the condottiero. Piero della Francesca's naturalistic style in this oil painting is also replicated in Sigismondo Pandolfo Malatesta Praying in Front of St. Sigismund , which he also painted the same year. This painting depicts Francesca kneeling in front of his patron saint, Burgundian King Sigismund. Both paintings show Sigismondo Pandolfo Malatesta in the same style and clothing.
Artists, such as Rogier van der Weyden, have clearly been an influence in these paintings for the texture of skin and hair emulates the Flemish style of these masters. However, some art critics believe that the painting may be a neoclassical fake due to the link between the two paintings, or that may have simply been a preliminary portrait of Sigismondo Pandolfo Malatesta. The International Gothicism of Italy is evident in the painting through the stance of the portrait and the expensive dress Sigismondo Pandolfo Malatesta wears. The dark background, however, is very unusual, for the subject takes up the majority of the frame and is not surrounded by biblical references or iconography of Italy. Consequently, the portrait relies on the geometric subject to balance the colouring and proportions of this painting.
Sigismondo Pandolfo Malatesta was a major patron of Italian Renaissance art, and this shows in the portraits painted by Piero della Francesca. He was also light-heartedly nicknamed The Wolf of Rimini due to his impressive bravery and candour in the Venetian force's 1465 campaign against the Ottoman Empire. The Portrait of Sigismondo Pandolfo Malatesta now resides in the Louvre Museum, Paris, sold to the museum by Roberto Longhi. Despite its questionable validity, the Louvre has also been certain in its attribution. Previous to this, it belonged to the Russian Imperial Art Collection until 1889.