The bankruptcy was long before the progressive system, like 5 years before. For 20 years Singer has said he lost 250K over a 4 year period before using the progressive system starting about 1999.
You framed the timing as a question here. But you have a habit of starting out with a speculation then later stating it as a fact.
You haven’t proven anything about Singer. All you have is conjectures that you always start calling facts at some point.