This could make for a few awkward moments around the DFL campfire [see update]. Richard Painter has leveraged his two years as chief ethics attorney in the George W. Bush administration into media gigs as a vociferous critic of Donald Trump. Today, Painter launched his effort to use the US Senate as his next platform, but that will upset the careful strategy put together by Chuck Schumer to keep Al Franken’s seat safely in the hands of Democrats:

Richard Painter, a longtime Republican who was chief ethics lawyer for George W. Bush’s White House, intends to run for the U.S. Senate in Minnesota this year as a Democrat, according to a filing he made recently with federal elections officials.

Painter, a persistent and frequent critic of President Donald Trump on national cable TV news appearances and on Twitter, is expected to announce his candidacy at a Monday news conference.

He’s running for Democrat Al Franken’s former seat. Franken resigned Jan. 2 in the wake of numerous sexual harassment allegations.

Gov. Mark Dayton appointed Lt. Gov. Tina Smith to be his successor. That seat is up this fall in a special election, and Smith has said she intends to run for the right to finish the term through 2020.

Let’s remember how Smith ended up in this position. Outgoing Minnesota governor Mark Dayton originally selected her to be a placeholder until a special election could be held in November, leaving the DFL to decide on its own who to nominate for the final two years of Franken’s term. That, however, created a risk for losing a seat that Schumer didn’t want to take. He twisted Dayton’s arm to pick someone who’d run in the special election to avoid a primary fight, and Dayton in turn twisted Smith’s arm to commit to running for the office — a decision made presumably easier by the implicit promise that it wouldn’t involve a tough primary battle.

What happens now that Painter has thrown in with the Democrats? Does Smith, whose only electoral experience until now was as Dayton’s running mate in 2014, bail out? Smith has kept a low profile in the Senate over the last four months, but she’s raised a lot of money since then, clocking in at just a skosh under $2 million as of last week. She’s not going to leave after collecting that much cash, which means that Painter will have to eat into her donor base to compete. He’s much more likely to find out-of-state resources for that fight than Smith, who’s been all but invisible since being sworn into office.

Karin Housley, the lone Republican in the field, has just under $700,000 but so far has no primary opponent. The DFL might have to raise a lot money — and spend it — in the primary cycle with these two going after each other, which is remarkably similar to what they’re currently doing in the gubernatorial race. That could allow Housley to keep her powder and cash dry and go into the general election with a big advantage.

The Washington Post’s Amber Phillips posits that it’s Donald Trump who’s promoting Painter into an electoral candidate in the opposition party:

Despite his Republican background, it’s not a coincidence that Painter has decided to run for office as a Democrat. The Trump era has opened the door for Painter to run for Senate. His candidacy is getting a big boost, if not being launched, thanks to Painter’s high profile as a Trump critic on Twitter, cable TV and other news media.

And from retiring Sens. Jeff Flake (R-Ariz.) and Bob Corker (R-Tenn.) to dropping poll numbers among Republican voters for Trump critic Sen. John McCain (R-Ariz.), there’s plenty of evidence that being a Republican and a Trump critic will cost you politically.

Therein lies the irony of politics in the Trump era: For all his criticism of the president, Painter has become prominent enough to run for a U.S. Senate seat because of help from Trump’s presidency.

Well, perhaps, but maybe Phillips ought to consider why Painter chose to run as a Democrat against an incumbent in the primary rather than in the GOP’s open primary. He’s bucking the party establishment to do it when he could have gotten a free ride from the DFL to take out Housley, who supports Trump. Trump came closer to winning Minnesota in 2016 than any other Republican since Richard Nixon succeeded for the last time in 1972, losing the state by less than two percentage points.

Was that a fluke, an artifact of having a truly terrible opponent on the Democratic ticket? Maybe, but it might also indicate that Minnesotans aren’t as anti-Trump as the DFL thinks, and that running a 2018 campaign on what happened in 2016 is a very dicey proposition, especially with two first-time candidates vying for the opportunity to make that case.

Update: My friend ChrisOfRights on Twitter reminds me that I need to define DFL. It means “Democrat Farmer Labor,” and it’s the Democratic Party in Minnesota.