As the hours passed with still zero precincts reporting results, it appeared there were no options left but to remain patient and hope for the best: the Iowa caucus would not be decided until the following day, at the earliest.
Reports of a failing app and "inconsistencies" in results began trickling in, but still no official numbers were coming in, upsetting campaign teams and frustrating caucus-goers, not to mention politicos across the country.
And then this happened:
"Tonight, an improbable hope became an undeniable reality," Buttigieg told his supporters, in what sounded like an undeniable victory speech. After noting that "we don't know all the results," he added, confidently, "Iowa, you have shocked the nation."
"Because, by all indications, we are going on to New Hampshire victorious!" he continued, beaming.
While his supporters were clearly excited by his winning tone, it was a note that played much less triumphantly outside of that room for all too many. His aggressive tweeting doubled-down on the theme that he was the winner of the night, despite relying only on internal data gathered by his own team.
In a moment of confusion, Buttigieg's premature claims of victory had the optics of turning away after throwing up a three-point shot and raising your arms high above your head before you've heard the swish of the net. When you go there with it, you better hope your instincts are right, because if it takes an unfortunate bounce off the rim, you're going to look awfully foolish.
Merely Buttigieg's willingness to take such a strong stance suggested he had good reason to believe he did well in Iowa. As some numbers begin to come in, showing both he and Sanders having had a strong showing, it's clear his team was right to feel confident. But how confident?
Both Buttigieg and Bernie Sanders have released internal numbers, each showing themselves leading, clearing wishing to give the appearance of a distinctive victory; especially on Buttigieg's side when paired with the boasting.
Buttigieg began to strike a more cautious tone following his rally with supporters. In an interview with CNN's John Berman, he stressed the importance of waiting for the results and said when he declared victory, what he really meant was he was taken by the "extraordinary" support he received in "rural areas, suburban areas, and urban areas."
Buttigieg's confidence prompted criticism from Sanders, who asked how one could declare victory without any official numbers being yet released.
Many of Sanders' followers were also displeased, with "#MayorCheat" trending on Twitter.
Buttigieg stepping into the spotlight as the seemingly self-described winner also prompted some conspiratorial thinking, with news of Buttigieg's connection with Shadow Inc., the company responsible for the disastrous app that failed on Monday, being read by some critics as a sign of something nefarious.
A Buttigieg campaign official told NBC News the campaign contracts with the tech company for text messaging services, as has Joe Biden's campaign. The official said the campaign has not worked with the company on any apps.
Those inclined to look for dots to connect, whether they make up an accurate picture or not, are also pointing to the pulling of The Des Moines Register poll after the Buttigieg campaign raised concern over a respondent reporting his name was left off the list of candidates when a pollster asked her who she was supporting. Recent Iowa polls showed Sanders and Biden alternating leads.
While these theories lack solid evidence, and while Sanders is also coming in for some criticism for touting his own internal figures, the controversy is taking the wind out of the sails of what should be a big moment for Buttigieg, who as a newcomer still needs to prove himself to the nation.
A win in Iowa will still be monumental, not to mention historic as a gay candidate, but it will now come with a newfound scrutiny even more intense than he could already have expected as a front-runner. Worse yet, if he doesn't win, his unforced error will make an otherwise respectable second place finish have the feeling of a mild embarrassment.