When David Ortiz signed his first contract with the Red Sox in January 2003, the Patriots had already hoisted the Lombardi Trophy once.
By the time Ortiz retired with the Red Sox in 2016, Boston captured another eight titles — including three more Super Bowls, three World Series titles, one NBA championship, and a Stanley Cup.
In total, Boston has won six Super Bowls, four World Series, two NBA Finals, and one Stanley Cup since the turn of the millennium.
But which title does Ortiz — who won three with the Red Sox over his Hall-of-Fame career — cherish the most?