08/01/2014 11:07 pm ET Updated Aug 02, 2014

For Alison Lundergan Grimes, McConnell Is The Least Of It

PADUCAH, Ky. -- Two key features of Democrat Alison Lundergan Grimes’ drive to oust GOP Senate leader Mitch McConnell were on display here Friday within a few hours of each other.

In an abandoned gas station on the outskirts of town, Grimes opened a local headquarters and drew an impressively large and pumped-up crowd of some 300 supporters who like her -- but like even more that she may “Ditch Mitch.”

Later, seated as a tiny dining table in her campaign bus, she carefully answered or swatted away our questions about immigration, the Middle East, marijuana and tax policy in a disciplined -- and successful -- effort to make no news, and to guard her political flanks in every direction.

A Democratic electorate that loathes McConnell, a diligent ground game and rigorous message discipline have combined to keep the 35-year-old Kentucky secretary of state neck-and-neck with McConnell since she announced her challenge a year ago.

What now? After talking with strategists, organizers, elected officials and observers here in Kentucky and elsewhere, I’ve compiled a list of challenges that Grimes confronts:

Stay Close. Democratic campaign bundlers and mega-rich independent donors around the country have gotten more interested in the Kentucky race, wondering if it's the real deal.

As summer in the Hamptons and the Vineyard turns to fall, Grimes needs polls to stay within the margin of error as these big shots make their late calls about where to invest. Many would be happy enough with McConnell. But if Grimes is to pull off the big upset that saves the Senate for the Democrats, these donors would want in on that action -- to assure their access to the Senate either way.

Go Deeper. Grimes, a lawyer from a deeply political family, is smart and well informed, but her campaign strategy isn’t designed to show what she knows. Instead, she is trying to take advantage of her mere two years in public office, which gives McConnell little of substance to attack. She sticks to her effective talking points -- such as the need to raise the minimum wage and ensure pay equity for women –- but speaks little about most everything else.

It’s not clear that this will work all the way to Election Day on Nov. 4. Three months is an eternity in politics. Grimes will need deeper, more specific proposals to feed into the discussion. And, after all, she would become a key figure if she knocks of McConnell -- and the Senate at least used to deal with serious national and global matters.

Louisville and Lexington. There are many Kentuckys; it is a varied and fractured mix of regions, cultures and even topography. But it’s clear which Kentucky is most important to Grimes: The urban one, especially in Louisville (Jefferson County) and Lexington (Fayette County). Rep. John Yarmuth of Louisville is the state’s lone Democratic member of the House of Representatives; Lexington is home to the University of Kentucky. Both have the state's only substantial African-American populations. “She’s GOT to get every single vote she can out of Louisville and Lexington to have a real chance,” said Kentucky's Democratic attorney general, Jack Conway, who is running for governor next year.

Women. Grimes can sound like a Southern fried suffragette, and she is aiming her main appeal directly at women voters in rural as well as urban areas. She attacks McConnell ceaselessly for his votes against pay equity and violence-against-women measures. A group called Emerge Kentucky has worked hard to recruit women for office, and provides a network for candidates such as Grimes. The trick now is getting every female who “leans Grimes” to the polls or to an absentee ballot. That is sometimes hard in a culturally traditional state, where white men trend strongly toward the GOP, while a fair number of their wives are leaning the other way. “Especially among seniors, it’s hard to separate the wives from the husbands,” said Ray McLennan, a retired IRS agent from Paducah who has spent years studying the data.

Number Crunching. Democrats still hold a huge registration advantage in Kentucky. It is said -- and it may well be true -- that if Grimes can turn out every last voter who dislikes McConnell and at least tolerates her, she will win.

That’s where numbers come in. Like everything else, turning out the vote has been transformed with algorithms and big data. Grimes said she'll have state of the art in both, and will be able to concentrate staff and volunteers in precisely the right places in the commonwealth. They need to be right, and as effective as any Democratic effort in the state since the legendary Wendell Ford.

Coal. McConnell’s guilt-by-association attacks focus on Grimes’ alleged ties to President Barack Obama, who is widely disliked in the state, and even to the otherwise fairly obscure Democratic Senate Leader Harry Reid of Nevada. Both are seen in Kentucky as “enemies” of the coal industry because of their support for limits on carbon emissions and other environmental measures. Grimes has tried to outflank McConnell by being a strong advocate of “clean coal” technology, and by pointing out that McConnell’s 30 years in Washington hasn’t stopped the EPA from imposing new rules.

But she may have to do more to minimize her losses in the coal regions of Eastern and Western Kentucky. She is campaigning in Appalachia next week with the ever-popular (especially in Kentucky) former President Bill Clinton. But as charming as he is, and as capable as he is of, as one local pol said, “bubba'ing it up,” that won’t be enough. Grimes will have to demonstrate a better understanding of, and concern for, the tenuous state of industries and populations that rely on cheap electricity rates.

Ride The Local Races. In presidential years, Democrats' huge voter registration advantage doesn’t seem to matter. Clinton was the last Democrat to win here, in 1996, and Obama lost in 2012 by 18 points. But “off years,” officials in the state’s 120 -- yes 120 -- counties all are on the ballot, along with state legislators. The Kentucky House, the last legislative body in the South (not counting West Virginia) to be held by Democrats, is under threat. The Grimes campaign hopes to ride that concern and the other local races.

Be Ready. So far, Grimes has shown that she can run as nasty a campaign as McConnell can -- a compliment of sorts in these times. But the boys from opposition research and the big outside conservative money will spend whatever they can to get control of the U.S. Senate. “We’ve got to be ready come Labor Day,” said an adviser to the Grimes campaign. “That’s when they stick the corncob up your butt.”



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