In addition to the Bernini, the Diamond collection features a deeply curated selection of rare and important Old Master sculpture. Among them is Jörg Lederer's polychrome limewood figure of St. Sebastian (estimate $600,000/1 million), a favorite subject in early wood sculpture. Depicting Saint Sebastian partially naked in a contorted pose, Lederer displays the brilliance and inventiveness of his craft in this exceptional and dynamic polychrome wood figure. Lederer’s design and skill with the chisel place him beside the great masters of German gothic wood sculpture. Many of his workshop’s altarpieces have been lost and the present sculpture appears to be the only surviving full figure of the saint attributable to the sculptor. It is a remarkable and rare discovery, with the artist's work infrequently appearing at auction.

Girolamo Della Robbia’s Madonna and Child (estimate $300/500,000), circa 1510, is a quintessential work of the Florentine Renaissance. The glazed terracotta sculpture is a beautifully modeled variant of the traditional Marian theme which appeared in various media during the Florentine Renaissance. The copious garland of fruit, vegetables, and flowers is modeled with pronounced naturalism and spiritedness and it surrounds an image of domestic intimacy and great devotional power. The pure white glaze illuminates the figures’ innocence and purity further underscoring the potency of this image. Della Robbia’s works were popular among Florentine patrons as decorations for their homes, and were usually acquired to mark significant family events such as marriages and births.

The collection also features a significant group of paintings, including a pair of magnificent canvases by Dosso Dossi, one of the most innovative and idiosyncratic artists of the Italian High Renaissance. This pair of canvases, The Sicilian Games and The Plague at Pergamea (estimate $3/5 million), are sections of the artist’s ten-piece frieze of scenes from the Aeneid commissioned by Alfonso d’Este (1476 – 1534), the Duke of Ferrara, for the decoration of his private study. Determined for the interior to reflect not only his personal passions, but his intellect and cultural imminence, the Duke acquired a superlative series of paintings from Italy’s most preeminent artists, including Giovanni Bellini’s Feast of the Gods (now in the National Gallery, Washington); Titian’s Bacchus and Ariadne (National Gallery, London), the Bacchanal of the Andrians and the Worship of Venus (Museo Nacional del Prado, Madrid). Above these large canvases hung Dosso’s exquisite frieze, its subject inspired by Virgil’s epic poem, the Aeneid. The specificity and detail with which Dosso describes Virgil’s epic poem through these surviving canvases show that Dosso did not simply synopsize the journeys of Aeneas, but chose instead to select specific episodes from the text that reflected the aspirations and favored pursuits of his esteemed patron – scenes of games, hunting and leisure.

The collection is further highlighted by an impressive triptych of The Nativity, The Adoration of The Magi, The Presentation in The Temple by Pieter Coecke van Aelst (below, estimate $2.5/3.5 million), one of the most important artists of the Northern Renaissance. This very early work, executed circa 1520-25, and fully intact in its original frame, is not only remarkable for its size, and excellent condition, but for the originality of Coecke’s iconography and use of color; the overall composition and fine details in the fabric patterns, still life elements, and landscape completely encapsulates painting in the Northern Renaissance. Following its re-attribution to the artist, the present work was the centerpiece of The Metropolitan Museum of Art’s exhibition, Grand Design: Pieter Coecke van Aelst and Renaissance Tapestry in 2014.

Filippino Lippi’s Penitent Mary Magdalene Adoring the True Cross in a Rocky Landscape (estimate $2/3 million), is a hauntingly beautiful private devotional work datable to the late 1470s, a period in which the artist was adhering to the style of his second teacher, Sandro Botticelli. A cult devotional figure in 14th-century Florence, Lippi emphasizes the ascetic life of the penitent Mary Magdalene, by showing her emaciated figure as all bones and sallow skin, and her hair has grown so uncontrollably that it doubles as a garment. The extreme devotion of the saint evokes an emotional response in the viewer, much like Donatello’s sculpted version of the Magdalene for the Baptistery in Florence (circa 1453-55), which was indeed a source of inspiration for Lippi, as were Florentine sculptures throughout his career.

Several significant works of contemporary art showcase the diversity and range of the Diamond collection. Bill Viola's Ablutions (estimate $70/100,000), a video diptych mounted on two plasma displays installed prominently in Hester's dining room behind the head of the table, plays a loop of two people washing their hands. Barry X Ball's Envy (estimate $80/120,000) is more closely associated with the Old Master sculpture in the Diamond collection, as the work is modeled after a 17th century sculpture by Giusto Le Court, a sculptor who is represented in the Diamond collection by a terracotta sketch model circa 1690 of St. James the Less, located in Ca' Rezzonico in Venice. Large-scale three-dimensional works by Dustin Yellin and Xu Zhen further round out the contemporary offerings.