Mitt Romney’s fundraising team might be popping champagne corks Monday, celebrating a second straight month of more than $100 million in donations — easily outpacing Obama. His communications team? Not so much.

While Romney is finally overtaking Obama in the money race, the last few weeks have been among the most difficult of his political career. Polls show voters see Romney in an increasingly negative light and Obama making progress in swing states, where he leads everywhere but North Carolina in the PollTracker Average.

Romney has a compelling campaign message (the economy stinks, elect a businessman to fix it), but attacks from the Obama campaign and his own missteps have stopped him from focusing on it for more than a day or two at a time.

Here’s a timeline of Romney’s cruel summer, beginning in July:

July 1: Romney begins the month on vacation in Wolfeboro, N.H. The previous couple of weeks had already been among the most intense of the election, marked by the Supreme Court’s decision to uphold the core of the Affordable Care Act and a new spate of tough Obama attacks pegged to a Washington Post report on Bain Capital’s investments in companies considered “pioneers” of outsourcing. Both stories invited recurring problems for Romney.

July 2 : Top Romney adviser Eric Fehrnstrom breaks with GOP talking points, calling the ACA’s mandate a “penalty,” not a “tax.”

July 3: Foreshadowing trouble ahead, Mother Jones publishes multiple stories on Romney’s purported exit from Bain Capital in 1999, noting that Romney’s name still appears on SEC filings related to later investments.

July 4: In a confusing clarification, Romney tells CBS that the mandate in the ACA is indeed a tax — but insists the mandate in his Massachusetts law is not.

July 5: Incensed at Romney’s handling of the health care decision, the conservative Wall Street Journal publishes a scathing editorial warning he’s in danger of blowing the election. It begins: “If Mitt Romney loses his run for the White House, a turning point will have been his decision Monday to absolve President Obama of raising taxes on the middle class.”

July 6: In a welcome break from the ongoing health care fight, Romney holds a press conference in a New Hampshire hardware store to slam the president’s jobs record after a weak employment report. It marks one of the few days the Romney campaign manages to convey a strong economic message.

July 10: TPM finds SEC filings listing Romney’s “principal occupation” as “Managing Director of Bain Capital, Inc.” after he says he departed the company to run the Olympics.

July 11: Romney is booed at the NAACP conference for pledging to repeal Obamacare.