In 2006, the Chicago Tribune‘s editorial page encouraged Barack Obama to run for president even before he had officially declared himself a candidate. The paper backed Obama during his first race for state senate, in 1996. It endorsed him again in his unsuccessful congressional race in 2000 and in his winning U.S. Senate race four years later. So, does this mean he’s got the paper’s endorsement come November?

No—not if history is any indication. The last time the Tribune backed a Democratic presidential candidate was in 1872, choosing Horace Greeley, a newspaperman-turned-politician, over the Republican incumbent and native son Ulysses S. Grant. (Technically, Greeley ran under the "Liberal Republican" banner but was officially endorsed by the Democrats.)

And like Grant, Obama won’t get a free pass just because he’s the local guy. "We’re electing the best president for the nation, not for Chicago," says the retiring Tribune publisher, Scott Smith. (The publisher weighs in with the edit board on its endorsement decision.)

Still, despite the Trib‘s century-long track record of picking Republicans, the paper’s editorial page editor, Bruce Dold, insists that the choice of Senator John McCain of Arizona is by no means a slam dunk: "Each race stands on its own," he says.

Except for Abe Lincoln in 1860, being a native son has been a counterindicator of the Trib‘s endorsements. The last local nominee for president on the general-election ballot was ten-term Illinois Republican congressman John Anderson, who ran in 1980 as a third-party candidate after losing to Ronald Reagan in the GOP primary. The Trib editorial board, which had endorsed Anderson in the primary, threw its support to Reagan, the GOP’s standard-bearer. Before that, in the 1952 and 1956 presidential campaigns, the paper twice backed Dwight D. Eisenhower against another native son, Governor Adlai E. Stevenson.

Ultimately, say Dold and Smith, the board’s endorsement will boil down to which candidate shares more of the paper’s guiding principles, which are described as being "traditionally conservative" and which strongly advocate for "limited government" and "free markets." (You can view them online at chicagotribune.com/principles.)

Dold says the board will meet a few weeks before the November contest to start discussing its endorsement. Does he expect a vigorous debate? "It always is," he says, adding: "I’m enthusiastic about both these candidates—it’s a wonderful choice to have."

And what about the role of Tribune Company’s new chairman, Sam Zell? He has publicly pledged to keep his personal politics out of the paper, but we’ll see.

Photography: (Anderson) Arthur Grace/Zuma Press