Sun Country Airlines flew into financial and reputational turbulence over the Christmas holidays.

Passengers were upended by a widely publicized software collapse by an airline vendor. The shutdown and reboot Dec. 27 and 28 displaced 8,000 passengers. The mess was compounded by COVID-19 and bad weather that taxed the entire airline industry.

"It boggles the mind," said Paul Omodt, a veteran communications executive who flies 100,000-plus miles a year. "Sun Country has a smart CEO, but they made unforced errors. And those are the harder ones to forgive."

Sun Country, Omodt said, has a long road to gain passengers' trust back.

"Sun Country is a vacation airline that doesn't have that many flights," he said. "You say, 'Next time I'll just go to a bigger carrier.' When you ask people about Sun Country, they say [management] couldn't fly its way out of a paper bag."

CEO Jude Bricker said the breakdown with the software came at the absolute worst time for a leisure airline, in a weekend with peak demand. AIMS Airline Software's backup system also failed.

The result was 32 roundtrip flights canceled. Customer service lines were jammed, and aggrieved passengers mocked Sun Country on Twitter and Facebook. The carrier is still working to compensate disrupted travelers.

The financial damage will be quantified in the upcoming 2021 earnings report.

"We assess [financial] damage as it goes," Bricker said in an interview last week. "The hard part is to assess brand and reputational damage. We probably won't know for a while. We had been doing very well with improved on-time [and other] performance."

Omodt and other observers said this could haunt Sun Country for years.

Sun Country, under Bricker's four-year tenure, has gone from a laggard among U.S. carriers to a top-flight record in reliability, better customer service and profitable growth. It now has 2,000 local employees.

The 35-plane airline, a fraction the size of globe-spanners like Delta and United, posted record operating income of $96.2 million on revenue of $450.5 million during the first nine months of 2021 from its domestic scheduled, charter and cargo service.

Apollo Management, a New York investment firm, bought Sun Country in April 2018 for $188 million and spent more than $200 million on fleet and technology upgrades, according to securities filings. After its initial public offering in March 2021, the value of the company surged to $2 billion, before settling recently around $1.5 billion, or around $28 per share.

Sun Country insiders, including Apollo, have done very well thanks to stock sales since the IPO. Even though Sun Country says Bricker still has the second largest ownership stake among airline CEOs, he sold more than 90% of the shares he directly owned, according to securities filings.

Bricker said he invested about $6.5 million, virtually his entire net worth, in Sun Country's stock in 2017 at a split-adjusted price of $5.30 per share. After announcing that he would, he sold 1.2 million shares last fall for $31.28, or nearly $38 million in gross proceeds, according to public filings. That left Bricker with 77,000 directly owned shares.

Bricker still holds an additional 1.5 million shares through stock options granted to him by the board.

Rosanna Landis Weaver, executive pay program manager at As You Sow, which advises institutional investors and others on executive compensation, said: "It's not good governance practice to sell that high a percentage of holdings that soon after the IPO — or anytime. In fact, there's a growing interest among [outside] shareholders to require longer holding periods on stock just for this reason.''

Bricker benefited as his stock increased in value thanks to improved Sun Country performance that led to the IPO in a hot market. Bricker, who also was paid $540,000 in salary and bonus in 2020, said the option-share grant demonstrates his interests are aligned with Sun Country's long-term shareholder interest.

Five out of six securities analysts who follow Sun Country continue to rate it a "buy," according to Yahoo Finance.

But the airline industry is volatile and has lost more money than it's made over its history, noted Biff Robillard, a veteran Twin Cities investment manager who doesn't own Sun Country stock, but said its performance has improved under Bricker. Still, Robillard wouldn't be comfortable as an investor until he sees insiders buying more stock.

"They only buy for one reason and that's because they think the stock is going up," Robillard said. "They sell for lots of reasons. None are bullish."

Omodt said Sun Country's path to public redemption is to be transparent about what the airline is doing to fix its systems to avoid another crisis like in December.

"They need to be explicit about what they need to be," he said, "and they have to prove it over time."