McCaskill had a clear fundraising advantage over Hawley as of July 18. Her campaign had $6.6 million on hand, versus $2.3 million in the bank for Hawley, according to Federal Election Commission records.
Hawley has received slightly more of a boost from outside groups than his opponent. Those organizations have spent more than $16 million opposing McCaskill, while outside groups have shelled out nearly $14 million against Hawley.
Both McCaskill's campaign and outside groups supporting her, including the pro-Democratic Senate Majority PAC, have focused primarily on health care. They have targeted the Hawley-backed pre-existing conditions lawsuit.
"Health care, particularly concerns about pre-existing conditions protections, is probably the best weapon McCaskill has to use against Hawley," the University of Missouri's Squire said. "Hawley's campaign has yet to offer a convincing counter to the many ads being run against them on pre-existing conditions protections."
Hawley says he wants to shield pre-existing conditions coverage despite the litigation.
"Senator McCaskill would have you believe that the only way to cover pre-existing conditions is to keep all the failures of Obamacare," he said in a statement last week. "That's simply not true. I'm committed to covering those with pre-existing conditions, and we don't have to break the Constitution to do it."
The state attorney general, meanwhile, has focused more on McCaskill's character. He has cast the senator as a wealthy Washington elite who has not showed enough transparency about both her personal finances and political backers.
That strategy partly drove his response to McCaskill's Supreme Court vote, in which he contended the senator "runs her family business as a dark money operation."
While super PACs have supported McCaskill's re-election, the senator's campaign says she supports a constitutional amendment to overturn the Citizens United Supreme Court decision and other proposals meant to restrain the influence of money in politics. The Citizens United ruling found that political spending is a form of protected speech, which therefore gives corporations and unions more leeway to influence elections.
Many Democrats believe Kavanaugh, as a Supreme Court justice, would rule on cases in a way that further boosts the reach of money in politics.
A White House spokesman overseeing communications for Kavanaugh did not immediately reply to CNBC's request for comment.
— CNBC's Christina Wilkie contributed to this report.
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