Bostonians will awaken on Wednesday, September 27 to two faces on the front page of their newspapers and at the top of their news broadcasts: the winners of the preliminary election to serve as mayor for the next four years.

It will be, incredibly, only the second time ever that both of those faces are not white.

Barring a monumental upset, Tito Jackson will be the first black mayoral finalist in Boston since 1983. That was the year of the legendary, attention-gripping battle between city councilor Ray Flynn and community activist Mel King, to succeed Kevin White in City Hall.

King, for all the excitement his campaign brought to a race-sensitive city, never really stood a chance. Although the city’s black population was similar to what it is now—a little less than a quarter of all residents—the rest of the city was less diverse, less liberal, older, and more working-class than it is today. After virtually tying Flynn in the preliminary, with 29 percent of the vote each, King was crushed in the final November tally, 65 percent to 35 percent.

Thirty four years later, a much-changed Boston again will be presented with a racially balanced choice for municipal chief executive: 50-year-old, white, Irish-American, labor-leading incumbent Marty Walsh; and 42-year-old, African American, Roxbury-raised, Deval Patrick protégé Tito Jackson.

If you gave me those two profiles as finalists four years ago, in the race to succeed the late Tom Menino, I would have bet heavily on the latter candidate—and I suspect most other local pundits and political insiders would have too. Boston, now a majority-minority city with a sizable additional segment of progressive white voters, is eager to elect its first “New Boston” mayor.

While Walsh and Jackson might not really be so very far apart in either personal background or policy outlook, there is no question who comes across, in those day-after newspaper photos, as New Boston.

So, why is it so hard for most people—and virtually every pundit and political insider I speak with—to envision Jackson beating Walsh this November?

Trust me, I have trouble picturing it, too. There are so many obvious advantages for Walsh.

The mayor’s inherent power ensures nearly unanimous institutional backing, guaranteeing endorsements, donations, and campaign volunteers.

Walsh is a savvy enough politician to take advantage of all that, while also coming across as genuine, hard working, and immensely likable.

The city is thriving economically, with relatively few significant problems to make residents want a change in the status quo.

Plus, Jackson has thus far seemed to be an underwhelming foe, raising little money and struggling to gain traction with a coherent message.

And yet, when I think of those two images confronting Boston viewers the day after the preliminary election, I can easily imagine Jackson’s path to victory.

All it would take is for the contrast of those two images to spur Boston’s black residents to embrace, enthusiastically, the chance to elect the city’s first black mayor—adding themselves, along with other minorities and white progressives, to the bulk of John Connolly’s near-winning 2013 coalition.

Frankly, the numbers make that outcome seem easy.

Walsh won by fewer than 5,000 votes, out of 142,000 cast, in 2013. All of that, and more, came from the large margins he racked up in precincts that, in the preliminary, had shown a strong preference for a minority candidate.

There were 82 precincts that had given most of their preliminary votes to minority candidates. In those precincts—buoyed by endorsements from almost all of those candidates—Walsh beat Connolly in the November final by just about 8,000 votes. In the rest of the city, Walsh lost.

Voters of color, in other words, provided Walsh with his margin of victory.

If Jackson can simply run even with Walsh in those precincts, he would only need to retain most of Connolly’s coalition elsewhere to win. If he wins those precincts—as viable black candidates for other offices typically do—he can pile up thousands of votes there, to make up for any Connolly voters who flip to Walsh this time around.

And, what if voters in those precincts, and elsewhere in the city, actually get excited about electing Jackson—and turn out for him in much larger numbers than in the two-white-guys mayoral election of 2013?

A hint can be found in the 2006 Democratic primary, when those same voters got excited about the prospect of electing the state’s first black Governor, Deval Patrick.

Those same 82 precincts didn’t just vote in overwhelming percentages for Patrick, against opponents Tom Reilly and Chris Gabrieli. They came out in remarkably big numbers--13,000 of them casting votes for Patrick in that primary.

That was nearly 2,000 more than cast votes in those precincts for all five Democratic primary candidates in 2002, combined. Eight years later, again with no minorities running in the competitive Democratic primary to succeed Patrick, those same precincts reverted even more, casting fewer than 10,000 votes in total for Don Berwick, Martha Coakley, and Steve Grossman.

Turnout spiked for Barack Obama during his 2008 Massachusetts primary battle, helping him beat Hillary Clinton by 10,000 votes in Boston.

To date, no similar enthusiasm has attached to Jackson’s quest to become the city’s first black mayor. But it’s worth remembering that, early in their campaigns, neither Patrick nor Obama was forecast to do as well as they ultimately did in Boston. Patrick was thought to be a long shot, seen by many as a darling of white progressives but without traction among Boston’s largely working class black population. And Clinton enjoyed the backing of Mayor Menino and most of the city’s elected leaders.

There is one more thing to bear in mind. While it’s true that Mel King lost badly to Flynn in the final 1983 election, he received more than 69,000 votes—more than Connolly did in the 2013 final, and just 3,500 shy of Walsh’s winning tally in a city that had grown by some 80,000 people.

It’s entirely possible that the relatively low turnout in mayoral elections since 1983 is due to the absence of a candidate in the final pairing who appeals to the coalition King fired up back then. We know that the coalition is much bigger than it was then; we have not had a mayoral candidate, however, who could put its power to the test.

Tito Jackson might not be capable of being that candidate either. But we won’t begin to find out until Boston wakes up next Wednesday.