How will the country wind blow?

When the Country Music Assn. hands out awards Wednesday at 8 p.m. on CBS, watch to see whether the country establishment honors understanding or retribution as the better response to Sept. 11.

Alan Jackson’s thought-provoking hit “Where Were You (When the World Stopped Turning)” is vying for single and song of the year with Toby Keith’s saber-rattling “Courtesy of the Red, White and Blue (The Angry American).”

Both were monster hits on country radio and beyond, and helped give the singers the biggest albums of their careers. The two are competing in the association’s male vocalist, album and entertainer of the year categories as well.

“There’s a very strong chance this will be the year of Alan Jackson,” says Lon Helton, country music editor for Radio & Records, a trade publication. “He’s had not only two of the biggest songs out there in the past year, but he had a great tour and did a lot of other things.... It’s hard to imagine a better year than he enjoyed.”

Unless, that is, you’re Kenny Chesney. The Tennessee native scored a No. 1 debut on the pop and country album chart in May with his “No Shoes, No Shirt, No Problems” album, and the highest-grossing country tour of the year, selling more than $24 million in tickets to outpace perennial champs such as Jackson, Brooks & Dunn and George Strait.

That added up to a breakthrough year for Chesney, and the Country Music Assn. will want to recognize that. But in what category?

Keith also graduated to a new level of stardom in 2002 thanks to his “Red, White and Blue” single, “Unleashed” album (which debuted atop the pop and country charts in August) and those ubiquitous long-distance service commercials.

“The entertainer category is so strong,” Helton says. “It shows you what we in country have done in the last year when two artists elevated themselves from solid performers, solid album-sellers and hit single-makers to that next level where they’ve become known outside the country music world. To me that’s really what the entertainer of the year signifies.”

Where does that leave the race for entertainer of the year?

“That’s a good one to watch,” says R.J. Curtis at L.A. country station KZLA-FM (93.9). “I think Jackson has a better chance at winning song and single. I think the horse race for entertainer is between Brooks & Dunn and Chesney, and Chesney did have such a great year I have a feeling he may win it.”