The party couldn't even deliver a first-in-the-nation election night winner after a vote-reporting debacle in Iowa — where candidates spent months and millions of dollars vying for a glittering opening prize in their nominating contest.
It was a bold attempt to declare victory in the absence of a result, but the 38-year-old inadvertently cast an ironic judgment on a political train wreck.
The big Hawkeye State miss will be agonizing for whoever comes out on top but for any candidates who under performed -- perhaps former Vice President Joe Biden -- it might turn into a priceless lifeline.
The caucus nightmare also played right into the hands of a President spoiling for months to brand his rivals as weak, disorganized and even worse — plotting to rig the results to hand its crown to an establishment favorite. There's little doubt that Trump, who consistently erodes trust in institutions and governing systems, will weaponize such a narrative if it looks like he will lose in November.
The President pounced on the confusion early Tuesday morning.
"The Democrat Caucus is an unmitigated disaster. Nothing works, just like they ran the Country," he tweeted.
Meanwhile, Trump operatives are already spinning conspiracy theories and disinformation about what the Iowa Democratic Party said were "inconsistencies" in its results. Their aim is to create a narrative that tars the eventual nominee as illegitimate. And on the eve of his State of the Union address and two days before he's set to be acquitted in his impeachment trial, things cannot have worked out better for the President.
"It would be natural for people to doubt the fairness of the process. And these are the people who want to run our entire health care system?" Trump campaign manager Brad Parscale said, gleefully wringing every last drop of political advantage out of the Democratic blushes.
It could be that after the countless twists of the campaign and changes of fortune, Monday's snafu -- which a Democratic source told CNN's Mark Preston seemed to lie with a major coding error in the app -- will be a distant memory by November, especially if one of the candidates turns Trump into a one-term president. Democrats will get the last laugh then.
But there must also be questions about whether the Iowa mess is isolated -- or augurs a party ill-equipped in the states to take on Trump's formidable turnout machine, which is being built with his massive campaign war chest. And the importance of Iowa in the process of choosing a president magnifies the cost of its terrible night on Monday.
Iowa Democratic officials released results from 62% of the state's more than 1,600 precincts Tuesday evening. Buttigieg was in the lead with 26.9% of the state's delegates, which ultimately determines who wins the state's caucuses. Vermont Sen. Bernie Sanders was in second place with 25.1% of delegates.
"The reporting of the results and circumstances surrounding the 2020 Iowa Democratic Party caucuses were unacceptable," said Iowa Democratic Party Chairman Troy Price. "As chair of the party, I apologize deeply for this."
Was Buttigieg robbed?
Several campaigns were releasing their own data on the results, a process that is likely to only add to the confusion and devalue the eventual official result when it comes. It's not going to do much for the party unity that will be needed to beat Trump, which is already worrying party Democratic leaders.
And that final tally is not going to matter as much anymore anyway. There will be no Iowa victory parties before delirious Hawkeye State crowds in the blaze of on-the-night TV coverage.
The candidates have all skipped on to New Hampshire — meaning that when the vote counting does eventually produce a winner, the victor will be deprived of an often valuable Iowa bounce in polling and fundraising.
That's especially bad news for Buttigieg — who declared victory at well after midnight East Coast time, in a rousing speech that is now likely to become one of history's footnotes. When results finally started rolling in at 5 p.m. ET, Buttigieg was in the lead.
"By all indications, we are going on to New Hampshire victorious," the Indianan said.
If Buttigieg did in fact pull out the win he claimed, he will be the victim of one of the worst robberies in modern political history. It's not a stretch to say that a win would've compared with the seminal Barack Obama triumph in 2008 that sent the then-first-term senator on the road to the White House.
But the mix-up could also hurt Sanders, who also may have been heading for a strong night and will now be deprived of the media and fundraising buzz he could have expected.
Nevertheless, Sanders seemed happy his performance, predicting he was going to do "very, very well."
If Massachusetts Sen. Elizabeth Warren was destined to fall behind Sanders in Iowa, she'll get another chance to wrestle for the soul of the party's most liberal activists in New Hampshire.
But Biden, who appeared to be heading for a rough outing, may have caught the biggest break.
In a telltale sign that he performed below expectations, Biden's team raised doubts about the "integrity" of the caucuses -- showing its keenness to disregard any result that emerges later in the day on Tuesday.
Even if he now loses in New Hampshire and Nevada, Biden could pull off a win in his firewall state of South Carolina at the end of the month and essentially argue that the pre-Super Tuesday contests were a wash.
Perhaps the shrewdest move in the chaos of Monday night came from Minnesota Sen. Amy Klobuchar, who emerged on stage first and won a ticket out of Iowa that many observers doubted she could claim.
"We know there are delays, but we know one thing -- we are punching above our weight!" she said.
A sad day for Iowans
The vote counting mess was also an insult to the voters of Iowa, including Democratic activists who have spent months running the rule over a record party field and will now get a reduced payoff for their diligence.
Volunteers across the state gave up their time to mount the caucuses, and to canvass for candidates and their efforts will now be stained by an asterisk.
Given that many Democratic opinion formers have complained about the overwhelmingly white state's preeminence in a party that has an increasingly diverse racial coalition, Monday's epic fail cannot have come at a worse time.
Many campaigns have complained about the creaky caucus system -- not just in this cycle -- partly because it doesn't involve a secret ballot and is prone to vote-counting problems given its idiosyncracies.
Former Republican Sen. Rick Santorum -- who won the Iowa caucuses in 2012 but lost a knock-on advantage after it was initially declared Mitt Romney was the winner -- said on CNN that it was now vital for state officials to clear up any doubts about the probity of the caucuses.
One Iowa Democratic luminary called on everyone in Iowa politics and the media to take a deep cleansing breath, arguing that getting the final vote tally correct was now what mattered.
"Of course, Iowa Dems are taking their time to make sure the results reported are accurate. If there's a delay of several hours, to make sure the results are accurate, is that so bad?," former state party chair Gordon Fischer told CNN's Gloria Borger.
"We live in a different age, an age of super speed! Internet! Social media! People simply aren't used to waiting for anything anymore. Should the Iowa Caucuses remain first-in-the-nation? Absolutely, no question, without a doubt."
Still, the fast-moving electoral calendar waits for no one.
Candidates had a full slate of events in New Hampshire on Tuesday. And despite Iowa's bid to make amends, the Granite State may now become the de-facto opening night of the Democratic race in next week's primary.