It's a bold, outside-the-box move and, at least at first glance, a win-win situation for McConnell.
Benton is very well regarded in Washington as a grassroots strategist with an ear to the ground of the tea party movement. McConnell, meanwhile, is the leader of the Republican establishment who wants to avoid the kind of tea party uprising that brought down his protege, former secretary of state Trey Grayson, in the 2010 Senate primary. (Rand Paul trounced Grayson in that race.)
"It’s classic McConnell," said Billy Piper, a former McConnell chief of staff who was involved in bringing Benton on board. "He’s always prepared. He’s not just thinking about the next move – not just what’s around the next corner.
"It certainly is helpful with a segment of the electorate, we hope, but this is something that’s much bigger than that."
While the hire is certainly noteworthy, it's not altogether shocking. McConnell and Rand Paul have made nice since the 2010 primary, and the Senate minority leader made a point to praise his Kentucky colleague in a video played at the Republican National Convention two weeks ago. Rand Paul has made clear he will support McConnell in 2014, which goes a long way toward discouraging any potential GOP usurpers.
McConnell has also gone outside his inner circle before. He often hires a new media team for his reelection campaigns, and his 2008 campaign manager, Justin Brasell, was also an outsider coming off a big-time Kentucky campaign (Brasell steered Rep. Geoff Davis to victory in a marquee race in 2006).
"That's exactly what he's doing this time -- hire the best guy for the job," Grayson told The Fix. "In Kentucky, a divided Republican Party usually results in a losing candidate."
Benton isn't the first operative to bridge the gap between Paul World and the establishment. Before him, there was Trygve Olson, an establishment-connected former National Republican Senatorial Committee aide who joined up with Rand Paul after the primary in 2010 and then worked for Ron Paul's presidential campaign this year.
Olson said Benton's hire is big.
"This is like LeBron to the Heat," Olson said. "The best player is now on the best team, and there is no limit to how good the McConnell campaign can be."
As with the NBA star, though, the question is whether the new teammates can work together to achieve success. Benton, after all, has spent a good portion of his political career antagonizing the likes of McConnell and the establishment, and he's not just a Paul aide; he's a member of the Paul family (literally: he's married to Ron Paul's granddaughter).
In addition, the grassroots may not be thrilled about one of their own going mainstream.
At this point, though, there doesn't seem to be anything amounting to a backlash over this marriage, whether it be Rand Paul getting close to McConnell or Olson being hired by the Pauls.
As long as Benton is on the same page as McConnell, Republicans say, it's an ideal situation.
"There's not an expectation that anybody is gong to agree 100 percent of the time," Piper said. "But in Jesse’s case, just as when he worked with Congressman Paul, the boss’s politics come first."
McConnell survived in 2008 with 53 percent of the vote and, despite Kentucky's conservative lean, has faced his share of close races. He will surely be targeted in 2014, especially after Republicans went hard after his counterpart, Senate Majority Leader Harry Reid (D-Nev.), in 2010.
Democratic Gov. Steve Beshear is popular, will be toward the end of his second term in 2014, and Democrats will likely lean on him hard to challenge McConnell (he lost to McConnell in 1996).
But McConnell's biggest hurdle may be a potential primary.
The tea party wasn't as much of a force this year as it was in the 2010 primary season, but the grassroots is still more than capable of taking down a Republican who doesn't cover his bases (see: Lugar, Richard and Bennett, Robert).
Benton's hire should go a long way toward McConnell covering his bases.
And for a guy whose political career has been marked by survival, this is just the latest episode.