During the second set, Santiago, who is also an educator, performed two selections that both informed, and displayed his Puerto Rican roots.  The first song was a duet featuring only Santiago on trumpet, and Westbury on drums.  After explaining the significance of the the Spanish and African influences in the "Plena" music of Puerto Rico, Santiago and Westbury were joined by Giovanni Rodriguez (percussion), Michael 'Miqui' Gutierrez (alto sax), and Roland Barber (trombone) for a rousing drums and horns only rendition, with the horns replacing the "pleneras" normally played in this traditional form of Puerto Rican folk music.

Toward the end of the set, a birthday cake was brought out to celebrate the birthdays of the Barber twins (Roland and Rahsaan) and the audience was treated to cake, and a joyous New Orleans influenced version of Happy Birthday featuring the ensemble, special guests Rodriguez, Gutierrez, and both Barber brothers.  On the last number of the set, the ensemble was joined by saxophonist Evan Cobb, completing one of the most original and entertaining performances to date for the Contemporary Jazz series.