Media News Group CEO William Dean Singleton, whose 54-paper chain owns the Pioneer Press, tells Editor & Publisher that “many” of his editors are leaning toward endorsing Barack Obama.

That’s a bit man-bites-dog because Singleton is a renowned anti-union conservative and friend of President George W. Bush.

“In talking to our editors, it appears many of them are leaning toward Obama,” Singleton told E&P from a retreat for Media News’ publishers, editors and other newsroom leaders. “But they have not made a decision yet. All of the papers are represented. I am hearing that the economy and health care are the big issues.”

In 2004, the Pioneer Press — then owned by Knight Ridder — endorsed Bush over John Kerry. At press time, PiPress officials weren’t available to tip their 2008 hand exclusively to MinnPost.

Singleton’s comment is odd only in that it cites “editors.” Hopefully, he means editorial page editors, since the top newsroom editor is supposed to steer clear of the opinion section. And even editorial page editors aren’t always key players: publishers often weigh in and can overrule their staff’s pick.

Still, Singleton’s comments at least indicate his top journalists are split.

Most newspapers make their endorsements next month, although the Seattle Times, owned by the Blethen family, became the first major U.S. paper to endorse Sunday, opting for Obama.