20 year old 290- take the muffler off to check it- take a photo of the piston through the exhaust port.
I am willing to bet the piston is scored up and the saw has a pretty major air leak.
Plastic clamshells are well known to do this- I have several boxes of 029-390 saw wrecks here as they are a popular farmer type saw here.
Some form of pressure and vacuum test needs to be done at likely air leak spots- intake manifold, clamshell joint and main oil seals.
If the saw runs and idles- the Bubba test of spray can while running might narrow it down.
Is it a hard starter? Many pulls and then eventually fires up, idles a bit, runs out of puff and stalls?
Scored up and excessive ring wear = low compression, lots of rope pills add lots of mixed fuel to the cylinder and eventually add enough oil in there to take up the slack and it starts- then the excess burns off and it dies.
You could remove the spark plug, tip a teaspoon or so of oil down the plug hole, swill it around and put the plug back in. Try to start the saw as per normal. If it starts fairly easily and runs okay ish but smokes a lot- low compression is the problem.