BWIA - a long and difficult story indeed. BWIA was formed in 1940 as a BOAC (now BA) subsidiary and twice came close to breaking even during the first 20 years of its existence. However, in the late 1950s BWIA's losses mounted as it took on some long over-water routes (eg Trinidad-Jamaica-Nassau-Bermuda-New York) on behalf of BOAC, then was forced to drop them when BOAC brought in Bristol Britannia planes. With BWIA being seen as a possible challenger to BOAC for the international route rights of the then-existent West Indian Federation, BOAC planned to shut it down in 1961 but the T&T Government stepped in and saved it by buying 90% of it. (Ironically the Federation collapsed in that same year as Jamaica withdrew.) The T&T Government later bought the remaining 10% from BOAC (I am not sure what year that was, possibly 1964). With BWIA firmly in Trinidadian hands it shifted its focus from the northern Caribbean and eventually the Jamaican government took over BWIA's Jamaica base and, with help from BWIA itself and later Air Canada, formed Air Jamaica.
BWIA was still not profitable though and while in the 1970s it made some changes (ie stopping service to Tobago and several other islands and replacing the 727s with 707s in 1971 to increase capacity and introduce newer routes to YYZ and LGW, later LHR) it continued to lose money. By 1973, however, with the oil boom going strong the Government had no problem supporting it. So BW, while it actually grew and expanded services and equipment (a good thing), it also was involved with considerable corruption, including a massively over-financed deal to buy a DC-9-51 back in 1980. Loyal friends of the State got perks and places in the company and its competitiveness was low - it was always late, severe overbooking and so on - but in those days it was not seen as a major problem, as many other airlines served Trinidad and flew regional sectors on their international routes so, if say BW had a delayed flight between POS and BGI, one could go over to the AA or EA (Eastern) counter and get on their flight instead without hassle (unlike now!)
After 1981, though, the fall in the oil economy meant that T&T's economy was in recession. Many companies closed down and many lost their jobs. BW was largely spared the pains of the public sector because of its importance to the State (it was still fully State-owned then) and while the Government tried to invite the other island states to participate in it, it was always turned down. By the late 80s though BW's state was very precarious and in order to keep going it decided to sell 3 of its 4 TriStars to lessors and lease them back - the 4th TriStar was later also sold and leased back. To some extent that decision was mainly due to the State's financial insolvency at the time but it clearly reflected BW's being part of the problem.
The decision to privatize BW was long and hard in coming but it finally occurred in the early 90s. By this time several routes had been dropped and the fleet rationalised to the 4 TriStars and 9 MD83s. BW was privatized in 1994 with Ed Acker put in charge. Acker, however, added to the airline's problems by trying some radical restyling, introduction of Airbuses (not a bad thing in itself but the new planes were incompatible with BW's fleet at the time and the departure of Acker left the 2 A321s delivered as orphans, now rehoused in Turkey) and starting a rather ill-conceived route to Sao Paulo. Financial impropriety was also part of the problem and so when Acker was sacked the company was in a bad state. The subsequent management under Ken Gordon tried to clean up matters and indeed made significant headway in getting the airline back on track - until Gordon left after he was curiously labelled "pseudo-racist" by the then Prime Minister over an unrelated issue (which led to libel suits!). Enter Conrad Aleong at that point.
Aleong has run BWIA for the last few years with one interruption when he went to ALM in Curacao (I cannot recall the name of the Chairman who stood in between). Under him some good things have occurred, such as the new fleet of 737-800s, the Bwee Express regional service (although controversial because of BW's shareholding in LIAT with whom Bwee Express competed) and route reorganization. BW declared profits in 1999 and tried the IPO in 2000 to generate more revenue - but many in the know felt that BW's shares would not do well. They were proved right as the shared plummeted after being launched on the Stock Exchange. There seemed to be irregularities with the accounting and the valuation of its assets.
As for now, the accounting is part of the problem with BWee. Add to it the effects of 11/9/2001, the problems with operating its old fleet (TriStars in particular), the need to cut down the thick staff levels it has always had since the 70s in particular and the fact that it has cornered itself badly by going avidly after the VFR market to Trinidad, Guyana and Barbados while ignoring the tourist market which offers far more profit. Even at home in Tobago BW has been clearly run out of the tourist trade by BA, Condor and Monarch with Virgin coming soon.
So that's the story of BWIA - many difficult times indeed but in some instances politics and poor management have been at the heart of its woes. Hopefully it can be saved. In fact, it is likely it will be saved by the State if it were needed - the State may deny it up-front but behind it all they have pride to play for and would not let BW go under. If they did then Trinidad and Tobago would basically be left for Air Jamaica to take over - not entirely an easy pill to swallow, given the nature of Caricom relations.
Hop to it, fly for life!