By Jon Ostrower And Laura Stevens 

FedEx Corp. said Tuesday it plans to acquire as many as 100 new Boeing Co. 767 freighters, the largest order for the aging widebody jetliner that first entered service as a passenger plane in 1982.

The agreement with Boeing is worth nearly $20 billion at list price and includes a firm order for 50 new 767 freighter aircraft and options for 50 more of the jets, which carry a list price of $199.3 million, though buyers typically enjoy steep discounts on large deals.

FedEx, the large international express-package air carrier, has been hit by a multiyear slowdown in the global air-freight industry. The global market for air freight has only recently begun to rebound after years of recession following the global financial crisis. In recent years, shippers also switched to slower and less-expensive methods and FedEx's express business has struggled to maintain the same level of profitability.

The company has been restructuring its Express division, overhauling the aircraft fleet and buying new planes to improve fuel efficiency and adjust to demand. In addition, about 3,600 employees have accepted buyout offers and left the company.

In June, FedEx said it was accelerating retirements of planes both to reflect demand and to modernize its fleet, recording charges of $276 million. It retired 15 planes and 21 related engines, and said it would adjust the retirement schedule for additional aircraft.

FedEx significantly modifies each 767 jet for use as a cargo carrier, adding a new cockpit with large, modern displays. FedEx said it has firm orders for 106 of the freighters for delivery between 2018 and 2023. FedEx said that the order would have no impact on its 2016 capital spending, and would be immaterial to its fiscal 2017 spending.

While FedEx said in the announcement it had ordered 50 new planes, one is already on Boeing's books and three were previously committed. Those four jets were contingent on language in the contract allowing the company to cancel the order if Congress passed changes in labor law that would have made it easier for the company's workers to unionize. The order will add 49 new jetliners to Boeing's backlog.

Separately, Boeing earlier Tuesday said it won an order for five 777 freighters from Taiwan's Eva Air.

Boeing has delivered more than 1,000 767s, and the FedEx order breathes new life into the aging jetliner. The jet's future was largely earmarked as an aerial refueling tanker for the U.S. Air Force, the development of which Boeing is now struggling to complete.

Boeing on July 17 took a pre-tax $835 million charge against its second quarter earnings after it discovered an issue with the fuel system on its KC-46A aircraft, a heavily modified version of the 767. Boeing builds both the tankers and freighters on the same assembly line at its Everett, Wash., plant.

Write to Jon Ostrower at jon.ostrower@wsj.com and Laura Stevens at laura.stevens@wsj.com

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