There are just two days left for Bostonians to decide whether they want their next mayor to be Marty Walsh or John Connolly. The election will be held Tuesday, November 5, and is shaping up to go down in historic fashion – for it’s the first time in two decades that someone not named Menino will be occupying the City Hall office.

But that got us thinking, do either Walsh or Connolly possess the chops to become of The Hub’s most popular helmsmen? In the twilight of his career, Mayor Menino has an astonishingly high approval rating, as did many who came before him. So in the spirit of exercising our right to vote for our new municipal manager, we’ve compiled the five most beloved Boston mayors, in no particular order.

5. Tom Menino (1993- present)

Nicknamed ‘Mumbles’ for his distinctive Boston accent coupled with his tendency to speak an endearing verbal gaffe or two, the Boston Herald reported in 2012 that Menino boasted an 82% approval rating. That, and the fact that he’s made it a point to attend as many neighborhood-level events and ribbon cuttings as possible, has made Menino the standard by which the next mayor, and maybe even his successor, will be measured.

 

 

 

 

 

4. Kevin White (1968-1984)

Both Marty Walsh and John Connolly have cited Kevin White as having pulled Boston through turbulent times of racial tension and an economic spiral to a revitalized metropolis more tolerant of minorities. He is credited with invigorating Boston’s waterfront, downtown, financial district and Quincy Marketplace. His popularity was high enough to secure him four straight mayoral victories, as well as a massive commemorative statue outside of historic Faneuil Hall. Alas, his bids for Governor and Vice President were unsuccessful.

 

 

 

 

 

3. Maurice J. Tobin (1938-1945) / John Hynes (1950-1960) [Tie] 

 

 Both have notable pieces of infrastructure named after them and both held office just before a stark socioeconomic upswing in the City. The Tobin Bridge (as well as Tobin Hall at UMass Amherst), which carries Route 1 across the Mystic River and through Charlestown, is named after Maurice, who also held the positions of Governor and U.S. Secretary of Labor. His most notable local achievement was the creation of MassPort, though that took place during his two-year stint as Governor.

Hynes, whose name is recognizable for the massive convention center on Bolyston street and the T stop underneath, is the mastermind behind Boston’s iconic Freedom Trail, which is a line-guided tour of The Hub’s most historical locales. Hynes is also the creator of the Boston Redevelopment Authority, which set the stage for his successors to reinvigorate commercial and residential development in the city.

 

2. John F. “Honey Fitz” Fitzgerald (1906-1908; 1910-1914)

This guy spit such sweet game that they nicknamed him ‘Honey Fitz.’ The maternal grandfather of the late President John F. Kennedy, Fitzgerald boasts the distinction of being the first American-born Irish mayor of Boston. He was an early supporter of the modern day Boston Red Sox, and despite losing his bid for reelection only to win a second non-consecutive term, was able to persudade private business as well as state legislature to invest a combined $9 million in commercializing the waterfront.

 

 

 

 

 

1. James Michael Curley (1914-1918; 1922-1926; 1930-1934; 1946-1950)

Mayor of Boston, Governor of Massachusetts, and U.S. House of Representatives member, James Michael Curley is easily the most popular Mayor Boston’s ever had. Though he was in with the Irish Mob, Curley took down four mayoral elections, one of which he won while sitting in jail on felony fraud convictions. To this day, he’s memorialized by a statue in front of Faneuil Hall and a gob-smakingly good restaurant that bears his name.

 

 

 

 

 

 

Tomorrow is election day so be sure to find out where you’re eligible to vote and why it’s important.