It seems increasingly likely that Lexington Mayor Jim Gray, a Democrat, will throw his hat in the ring to take on Republican U.S. Sen. Rand Paul this year.
So it’s worth asking: Can Gray beat Paul?
Can the mayor reverse or pause the state’s rightward lurch, resuscitate a decimated Democratic Party and pull off what would be one of the greatest upsets in modern politics?
Probably not. But that doesn’t mean he shouldn’t try.
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After all, the guys in the White House and the governor’s mansion, not to mention that fellow with the hair that’s leading all the Republican presidential polls, all began their campaigns amid the widely shared and assumed certainty that there was no way they could win.
Still, even the most optimistic Democrat would have to concede that Gray’s odds of victory are long, and even with Paul’s bizarre and battered presidential campaign raising questions about his strength at home, the senator would by any objective measure be viewed as the favorite.
But that doesn’t mean there aren’t reasons for Gray to run, and it doesn’t mean there isn’t an argument to be made that he could give Paul a real fight.
Let’s start where most modern campaigns do — with money.
In addition to being mayor, Gray co-owns a successful family construction company. He is a very wealthy man who has demonstrated in the past that he is willing to spend his own cash on a campaign.
In 2011, Gray spent $900,000 on his bid to beat Jim Newberry. If he was willing to do the same upon announcing a Senate run, it’s remarkable how close he would be to achieving financial parity with Paul right out of the gate.
A viable U.S. Senate race would likely require a larger financial commitment from Gray, but he might be in a better position to raise money nationally than anybody else Kentucky Democrats might consider nominating.
Without any public polling to tell us how Paul’s presidential run or voting record have impacted voters’ views of him, Paul’s most obvious vulnerability is money.
At this point in his most recent re-election race, U.S. Senate Majority Leader Mitch McConnell, who was facing a primary challenge, had already raised $20 million and started the year with more than $10 million in cash.
We don’t yet know how much Paul raised last year for his Senate race — those numbers should be made public soon — but as of the last filing report, it was well south of $2 million and the bulk of his fundraising efforts have focused on his presidential race.
Depending on how deep he’s willing to go in his own pockets, Gray might start his race with more money than the incumbent.
And Gray will need every penny he’s willing to spare to introduce himself to voters and prepare for the inevitable and unrelenting attacks he will face.
Which brings us to the next question: Who has more baggage?
Paul’s wild and unenviable descent from “the most interesting man in politics” to the most interesting man to be kicked off a debate stage has been well-documented.
In addition to financial concerns, Paul’s votes on national security bills and budgets could make him vulnerable in a state with two major military installations and a high veteran population.
Put another way, Paul should be considered the favorite to win, but that doesn’t mean he’s not vulnerable.
But so is Gray.
Like any elected official running for higher office, Gray has a record, and that record contains high points and low points. The former makes for good ads for the candidate, and the latter makes for good ads for his or her opposition.
Gray’s profile as a businessman is arguably one of his greatest strengths, and he can point to his success in addressing problematic police and fire fighter pensions, as well as his overall high marks for managing the city, as proof that he knows how to get things done.
But Paul’s team certainly won’t miss the troubling crime numbers and stories coming out of Lexington, and nobody is going to miss the giant hole in the middle of downtown.
Additionally, you can bet that voters will hear an earful about how Gray made millions investing in a company called PurchasePro, a dot-com darling that went bust under the leadership of Lexington native Junior Johnson, who went to prison for securities fraud and witness tampering.
Suffice it to say, Republicans will fill out their opposition research books just fine, and Gray could be bloodied by what they find.
If they feel compelled to use it all.
And that brings us to the next question: How will presidential politics shape the race?
President Barack Obama will still be in office come November, and as we’ve seen in recent Kentucky elections, that alone might be enough for Paul to seal the deal.
Further, the idea that the political environment will be more friendly for Democrats if Hillary Clinton is at the top of the ticket is most likely wishful thinking on the part of Kentucky Democrats, who are running out of reasons to be hopeful for the future.
Clinton’s stances on guns and coal will make it all too easy to run the same kinds of campaigns we saw from McConnell and Matt Bevin, referendums on the president that Democrats have proven powerless to rebut.
Republicans might not need to hit Gray for whatever past personal and professional shortcomings he might have. It might be enough to simply remind voters daily that he is a Democrat.
And branding Gray as a Clinton-Obama Democrat would be a whole lot easier, less messy and less prone to backfire than running against his sexual orientation.
Yes, Gray is openly gay.
That will be all some voters need to know about him before making their decision. On the flip side, it’s all some national Democratic donors will need to know before getting out their checkbooks.
Social conservatism is not Paul’s bread and butter, and it’s unlikely that the libertarian Paul would all of a sudden decide that he wants to be the anti-LGBT candidate.
Paul has been able to grow his brand nationally with millennial Republicans, moderate Democrats and the technology sector in large part because he avoids some of the more common Republican rhetoric in this area. Keep in mind that when Rowan County Clerk Kim Davis got out of jail, there were two presidential candidates there to greet her and neither of them was Paul.
But regardless of whether Paul brings up Gray’s sexual orientation, it will be a factor.
It will hurt him in rural areas, and help him in Louisville and Lexington. It will aggravate him on the days he wants to talk about income equality and the media want to talk about his personal life. And it will serve to once again make Kentucky a central battlefield in the nation’s ongoing culture wars.
And that might be reason enough for Gray to run.
There were a lot of LGBT Kentuckians and liberal Democrats who waited through the summer with angry impatience for someone in their party to stand up for the taxpayers in Rowan County and offer a counter to the voices lining up in support of Davis.
They’re still waiting. Gray can be that someone.
It’s doubtful that Gray wants to run for the U.S. Senate just so he can answer questions about his sexual orientation or be politically martyred in the ongoing battle for equality.
He’s a businessman, not an activist.
But history tells us that oftentimes the men and women who break down barriers weren’t out to carry the banner of an entire race or creed. They just wanted to pursue the same opportunities that others enjoyed, and by fighting for those opportunities, the mantle of pioneer was thrust upon them.
And that brings us to perhaps the most important question of all: Is it worth running even if he can’t win?
There’s only one man who knows the answer, and he’s still making that decision.
It would be a brutal race, and no matter what either candidate does, it’s likely Paul emerges the winner.
But there are other kinds of victories to be achieved, and there are some fights worth fighting even if the outcome seems certain.
If Gray wants to take on those fights in an authentic and fearless way, he could stand to win a lot even if he loses.