Mayor Marty Walsh is coming up on his 2 year anniversary as mayor of Boston—which makes up only about 10% of his predecessor Tom Menino’s 20 year tenure in office. But with high approval ratings, a formidable war chest, and close working relationship with the state’s Republican governor, is Walsh already on track to be the city’s next “mayor for life?” And, more importantly, does he even want to be? Could an upstart challenger from City Council or beyond—like Tito Jackson, who made a name for himself in opposing the city’s Olympic bid, or popular City-Councilor-at-large Ayanna Pressley—knock him out of the seat?

Reporter Adam Reilly caught up with Gintautas Dumcius, Mass Live reporter and author of “This Way To City Hall,” and Boston Globe business columnist Shirley Leung, on the windswept steps of City Hall Plaza. We also chatted with Walsh’s one challenger in the 2017 race so far—Mary Franklin, an advocate for the families of homicide victims—and  WGBH News.org Senior Editor Peter Kadzis, who gave us a history lesson on Boston’s long line of colorful leaders.