Ten years after the Chicago Cubs ended their historic 108-year World Series drought, Roy Wood Jr. joins Bomani Jones on The Right Time for a special Time Machine Tuesday looking back at the unforgettable 2016 championship.

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Roy Wood Jr., a lifelong Cubs fan who attended Game 7 of the 2016 World Series in Cleveland, shares his firsthand experience watching Chicago finally win it all. From the emotional roller coaster of the Cubs' comeback against Cleveland to Rajai Davis' dramatic home run off Aroldis Chapman and the unforgettable rain delay, Roy explains what it felt like to witness one of baseball's most historic championships.

Roy also tells the incredible story of how Trevor Noah encouraged him to leave work at The Daily Show, buy a last-minute World Series ticket, and fly to Cleveland for Game 7.

Bomani and Roy revisit the Cubs' decades of disappointment, growing up watching baseball on WGN and TBS, the brilliance of Andre Dawson and Sammy Sosa, the heartbreak of the 2003 Steve Bartman game, and how Theo Epstein helped build the championship team featuring Kris Bryant, Anthony Rizzo, Javier Báez, Jon Lester, and more.

Plus, they discuss why the Cubs eventually broke up their championship core, the emotional cost of rooting for losing teams, and Roy's hilarious approach to raising his son as a New York sports fan.