Trump will campaign with his vice presidential nominee, Indiana Gov. Mike Pence, this week in the crucial battleground states of Virginia, North Carolina, Florida and Pennsylvania, where he'll host a town hall in Scranton on Wednesday.
The four-state swing will mark the first time Trump and his vice presidential nominee campaign at each other's side since Trump called on the Indiana governor to join him on the Republican ticket just before the Republican National Convention last week.
But while the two Republicans' chemistry will come under the microscope in those first campaign stops, the focus will also be on how the two men finesse their attacks on the Democratic ticket.
The swing comes days after Clinton tapped Sen. Tim Kaine, a moderate Democrat from Virginia, as her running mate.
The Trump campaign has already begun attacking Kaine by trying to paint him as part of the "rigged system" like the soon-to-be Democratic nominee. A senior Trump campaign adviser said Saturday the campaign will this week continue to draw a contrast between the Clinton-Kaine ticket and Trump's outsider appeal as well as poking holes in Kaine's record.
Trump has also opened a front on Kaine by pointing to the Virginia senator's support for the Trans-Pacific Partnership -- which Trump's own vice presidential nominee also supported -- in an attempt to draw supporters of Sen. Bernie Sanders to his campaign.
That effort comes as Democratic National Committee Chairwoman Debbie Wasserman Schultz announced Sunday her plans to resign her post after leaked emails revealed DNC staffers favoring Clinton in the primary between the former secretary of state and Sanders as well as Wasserman Schultz's own comments critical of Sanders' top strategist.
Trump has repeatedly suggested a "rigged system" kept Sanders from clinching the Democratic nomination, and Trump campaign chairman Paul Manafort touted the DNC emails as evidence the committee set up a "rigged system ... with the Clinton campaign."
"Now Hillary Clinton should follow Wasserman Schultz's lead and drop out," Manafort said in a statement, citing Clinton's storing of classified information on a private email server during her time as secretary of state.