William Heirens entered prison in 1946.
He did not leave again.
But the story outside the prison walls kept changing.
His legal challenges began early.
He claimed his constitutional rights had been violated.
He challenged the circumstances surrounding interrogation.
He challenged the plea process.
He raised questions about psychiatric evidence and the treatment he received after arrest.
Illinois courts repeatedly rejected efforts to undo the conviction.
Federal courts also declined to invalidate the guilty pleas.
Legally, Heirens remained the man who had admitted three murders.
But legal finality is not the same thing as historical certainty.
Over the years, journalists, attorneys and innocence advocates returned to the files.
And the more closely some of them looked, the more uncomfortable parts of the original narrative became.
Start with the lipstick message.
The image is iconic.
Red writing.
Erratic capitals.
A desperate plea.
It became the entire identity of the case.
Yet the link between that writing and Heirens was never as simple as later documentaries sometimes implied.
Several handwriting specialists either failed to make a convincing match or actively disagreed that the writing belonged to Heirens.
Herbert Walter eventually supported the prosecution connection, but his later conclusion differed from earlier comments about substantial differences between the writings.
Then, decades later, former FBI document examiner David Grimes reportedly concluded Heirens's handwriting did not match either the Brown lipstick message or the Degnan ransom note.
Even more important:
The lipstick message and ransom note themselves did not necessarily appear to have been written by the same hand.
That undermined one of the most psychologically compelling elements of the original case.
Perhaps there was never one taunting writer moving from Brown to Degnan.
Perhaps the crimes were unrelated.
Or perhaps the same offender deliberately disguised his writing differently.
The historical record cannot resolve that question with modern certainty.
Then came the hidden impressions.
The original investigation publicized the idea that indentation marks in the ransom note could connect it to another written source.
But later accounts of the FBI examination indicate federal analysts did not support the dramatic interpretation promoted publicly.
A clue once presented as ingenious forensic detection became, to critics, an example of how badly investigators wanted every ambiguous mark to point toward a suspect.
Then the fingerprints.
This is where the debate becomes hardest.
Supporters of Heirens's guilt have always pointed to fingerprints as the strongest physical evidence.
A print on Suzanne Degnan's ransom note was identified as Heirens's.
Authorities also eventually said a print in Frances Brown's apartment belonged to him.
Fingerprint identification in that period was already accepted forensic science.
And a legitimate print left on a ransom note would be enormously difficult for an innocent suspect to explain.
That is why even many writers skeptical of the handwriting evidence have treated the ransom-note fingerprint as the hardest evidence to dismiss.
But Heirens's advocates argued that the prints had serious problems.
They questioned documentation.
They challenged the number and quality of matching ridge characteristics.
They highlighted conflicting police statements about the Brown print.
They claimed the Brown impression looked unnaturally complete for a crime-scene print.
Attorney Jed Stone later publicly alleged that the Brown fingerprint evidence was fraudulent or planted.
Those claims were not ultimately accepted by courts as grounds to erase the conviction.
But they ensured the fingerprint evidence would never again be discussed without controversy.
Then there was the confession.
For decades, the public remembered that Heirens confessed.
That statement is true.
He signed a confession.
He pleaded guilty.
But context matters.
He was seventeen.
He faced execution.
His attorneys negotiated specifically to avoid the death penalty.
A later Illinois Supreme Court opinion records that his lawyers and parents participated in the decision to negotiate a guilty plea.
The courts found that process legally valid.
Heirens later gave a different interpretation.
He said he confessed because he believed the only other outcome was the electric chair.
In later interviews, he described the decision essentially as choosing to live.
That does not prove the confession false.
Guilty defendants also plead guilty to avoid execution.
But it makes the phrase “he confessed, therefore case closed” less useful than it first appears.
A confession given as part of a life-or-death plea bargain is evidence.
It is not necessarily neutral evidence.
Then there was Richard Russell Thomas.
Thomas had been investigated in connection with Suzanne.
He had lived in Chicago.
He had a medical background.
A handwriting specialist reportedly saw similarities between Thomas's writing and the ransom note.
Thomas at one point confessed.
He later recanted.
Police did not ultimately charge him.
Once Heirens emerged, Thomas largely disappeared from public discussion.
To Heirens's supporters, that looked like tunnel vision.
To supporters of the original prosecution, it looked like police rejecting a false confession once stronger evidence appeared.
Both interpretations have survived.
And then there was the most basic problem of all.
William Heirens never received the kind of trial people later imagined he had.
There was no dramatic jury verdict in which twelve citizens heard all this contradictory evidence and unanimously decided he wrote those words in lipstick.
The case ended with guilty pleas.
The forensic disputes were never resolved in a murder trial.
That distinction would follow Heirens for the next sixty-five years.
Because the longer he stayed alive, the more the question changed.
It was no longer simply:
Was William Heirens the Lipstick Killer?
It became:
If the most famous evidence is disputed, how certain can anyone now be about what happened in 1945 and 1946?
And William Heirens would remain alive long enough to ask that question from prison for more than half a century.