In February 2018, Hawaiian was rumored to be canceling its order for six A330-800s and replacing them with 787-9s. It was reported that Boeing priced the aircraft at less than $115 million, and possibly less than $100 million, each; the production cost of a 787-9 is between $80 million and $90 million. Boeing Capital also released Hawaiian from three 767-300ER leases in advance; these aircraft were to be transferred to United Airlines. Initially, Hawaiian refuted it cancelled its A330-800 order, but did not dismiss a new deal with Boeing. However, on March 6, 2018, Hawaiian Airlines confirmed the cancellation of the A330-800 order and the signing of a Letter of Intent with Boeing to purchase ten 787-9 aircraft, with options for an additional ten planes; the deal was finalized at the Farnborough Air Show in July 2018.
In August 2007, the Seattle Seahawks became the second sports team to begin using Hawaiian Airlines to travel to games. The Oakland Raiders, also of the NFL, have been flying Hawaiian Airlines since the 1990s. The two teams fly on Hawaiian's Boeing 767s to and from all their games. Two of Hawaiian's Boeing 767 aircraft have been fitted with decals of logos from the Seahawks and the Raiders.
Soon after, in early 1985, the company received the first two of its leased Lockheed L-1011 aircraft. One aircraft was used to launch Hawaiian's first scheduled operation out of Hawaiʻi, daily Honolulu-Los Angeles services. This new service put Hawaiian in direct competition with the major US air carriers for the first time in its history. Throughout 1985 and 1986, Hawaiian Airlines added additional L-1011s to its fleet and used them to open up services to other West Coast gateway cities such as San Francisco, Seattle, Portland, Las Vegas, and Anchorage, which placed Hawaiian in further competition against the major US airlines.
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ʻOhana by Hawaiian is a regional subsidiary carrier of Hawaiian Airlines. The service is operated using three ATR 42 turboprop airplanes owned by Hawaiian and operated under contract by Empire Airlines. The new service was slated to begin in summer 2013 initially flying to Molokaʻi and Lānaʻi, however the airline was unable to begin during that period due to Federal Aviation Administration delays in certifying ʻOhana's operation. ʻOhana by Hawaiian is fully integrated into the Hawaiian Airlines network.
In March 2003, Hawaiian Airlines filed for Chapter 11 bankruptcy protection for the second time in its history. The airline continued its normal operations, and at the time was overdue for $4.5 million worth of payments to the pilots' pension plan. Within the company, it was suggested that the plan be terminated. As of May 2005, Hawaiian Airlines had received court approval of its reorganization plan. The company emerged from bankruptcy protection on June 2, 2005, with reduced operating costs through renegotiated contracts with its union work groups; restructured aircraft leases; and investment from RC Aviation, a unit of San Diego-based Ranch Capital, which bought a majority share in parent company Hawaiian Holdings Inc in 2004.
Meanwhile, Hawaiian Airlines also entered the new international markets of Australia and New Zealand in 1986 with one-stop services through Pago Pago International Airport. Hawaiian also aggressively grew its international charter business and pursued military transport contracts. This led to a large growth in the company's revenues and caused its inter-island service's share of revenues to shrink to just about a third of the company's total.