The company has suspended new deliveries of the plane in the wake of the biggest crisis in its 103-year history.
Boeing also noted a loss of $2.33 per share for the fourth quarter of 2019, with revenue in the last three months of the year decreasing to $17.91 billion. Losses amounted to $864 million, mostly related to the $4.9 billion charged the company voluntarily took due to the 737 MAX groundings shortly before it announced its second-quarter performance.
Costs stemming from the grounding and production halt of the 737 MAX, its best-selling plane, is weighing on Boeing's financials.
A hefty charge could push annual results into the red for the first time in more than two decades, capping a disastrous year in which Boeing already lost its crown as the world's biggest plane maker.
The company in October had dropped production to 12 a month from 14 due to lower orders from China.
Calhoun rebuffed recent media suggestions that he was a Boeing "insider" ill-suited to introducing radical change, but acknowledged he had had a "front row seat" as a member of Boeing board for past 10 years and pledged to overhaul the company's culture. Boeing now expects to be hit with a $19 billion bill that could get even larger.
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"Rebuilding the relationships with our customers and our regulator in the process of getting the MAX back up is also critically important", said Calhoun when answering a question during Boeing's investors call, reiterating that the manufacturer is always "dependent upon these relationships".
The MAX has been grounded since March following two crashes that killed 346 people which opened the doors to intense scrutiny of Boeing's safety practices - and regulatory oversight of its productions - as well bruising congressional investigations which have revealed a troublesome culture at the aviation giant. Some said that if given an option, they would choose another aircraft.
Calhoun, a former General Electric and Nielsen executive who had been on Boeing's board since 2009, became CEO this month.
Some say Wednesday's share price rally-despite the disappointing earnings numbers-can be explained by the forward-looking nature of markets and confidence in Boeing's newly-appointed CEO. Some good news for the company came last week when the much-delayed 777X finally flew.
His task has been made hard after Boeing released a series of damning internal emails in which staff said the 737 Max programme was "designed by clowns and supervised by monkeys", and suggested they would prefer their families not to fly on the jet.
During a conference call with analysts, Calhoun said he was "optimistic about the future".