Let’s say you are locked up in jail after being convicted at trial.

As you sit in your cell studying your case files, you notice that your 33-year-old female prosecutor was writing official documents to your 56-year-old male trial judge and then scrawling a cute little hand-written “smiley face” at the bottom.

Do you think if you saw that your prosecutor had written a smiley-face note to your judge, you might want to call your lawyer?

C’mon down Gerson Pascual-Santana, who by the way happens to be a person of color, unlike the 33-year-old female prosecutor and the 56-year-old male judge, who are white.

So now the “smiley-face” case will soon be heard a single justice of the Supreme Judicial Court (SJC).

And the Massachusetts criminal justice system has another massive black eye.

The hack judge in question – Douglas Darnbrough – has already resigned. His young female friend remains on the job – if I could I would insert a smiley face here for her!

The only problem for the prosecutors is, they’ve told a bunch of different stories about who did and who didn’t do what to whom, and most of them contradict what the previous filings said.

Pascual-Santana was convicted in March 2023 of molesting his pre-teen stepdaughter, a charge he continues to deny adamantly to this day.

The first eyebrows were raised when the 33-year-old female prosecutor asked for two years in jail and one year probation for Pascual-Santana. Her 56-year-old friend gave the person of color 3-and-a-half years to serve and eight years’ probation.

The maximum allowed under law!

And so the 33-year-old prosecutor’s boss, elected DA Tom Quinn, got to issue a glowing press release about how tough he is on crime.

All was well until a few months later, when anonymous letters began arriving in legal circles in New Bedford. They’re all now in the public record, detailing how “Darnbrough is having an affair with one of the prosecutors (name redacted).”

“They have been in an affair since the end of 2022,” said the anonymous writer. “They go to the Carmines (sic) restaurant in New Bedford every Tuesday after work.”

Tawdry Tuesday, I guess you’d call it. Or maybe Two-timin’ Tuesday.

The letters kept coming. Defense lawyers started demanding to see the cell phones of both the judge and his young friend.

On Sept. 21, 2023, the judge stopped coming to the courthouse. On Oct. 10, he was reassigned to Plymouth District Court. He lasted at Plymouth until Oct. 12 – three days.

On Nov. 2, Darnbrough sent a letter of resignation to Gov. Maura Healey, effective Nov. 10. Then he sent a second letter to Healey, re-resigning, this time effective Dec. 30.

This was shocking, because state judges never quit, especially with no pension in the works, and now Darnbrough is out, O-U-T. (No smiley face for him.)

Darnbrough is the typical failed lawyer who fantasizes about becoming a judge. He has a second-rate education – Bryant College, Southern New England School of Law. He finally scored a minor hack sinecure as an assistant clerk magistrate in Taunton in 2013.

His record was so lackluster that his judicial appointment was about to fail in the Governor’s Council in 2016. Gov. Charlie Baker had to step in to break the 4-4 tie. And this is what the taxpayers got for their money. Thanks Charlie!

There is no way a payroll patriot like Darnbrough would have ever given up his $207,855-a-year early retirement unless there was no other option.

As for his 33-year-old female friend, she claimed there was nothing to the letters, or the smiley face, and is still employed by the district attorney.

Keep your friends close….

The problem for the district attorney now is the sequence of stories his office has told. That chronology is outlined in an amicus brief on Pascual-Santana’s appeal by the ACLU, the New England Innocence Project and the Mass. Association of Criminal Defense Lawyers:

“Unsigned letters arrive and allege that a judge and prosecutor engaged in an improper relationship and ex parte communications.

“After the letters arrive, the judge is absent and then resigns.

“The DA’s office initially suggests that no investigation was conducted.

“The DA’s office concedes a duty to investigate and claims that the DA’s office in fact did conduct an investigation.

“The DA’s office reverses course and claims it was the Trial Court that conducted the investigation, but provides no evidence of that investigation or its findings.

“The District Court refuses to reconsider its order denying discovery from the Trial Court and refuses to order any additional discovery from the DA’s office….”

In conclusion, the ACLU et al. argue that “there is no evidence that any entity within the Commonwealth conducted any investigation into these allegations, the DA’s office’s shifting unsworn representations are no substitute for such evidence, and a remedy is therefore warranted.”

Like, releasing Pascual-Santana. And then maybe turning over the cell phones of the 56-year-old disgraced ex-judge and his 33-year-old female friend. This case is, as the anonymous writer says, “just the tip of the iceberg.”

Who is this anonymous woman? Call her Madam X. Is she a “woman scorned?” The DA’s office seems to know who “she” is. In a Jan. 29 filing, the DA mentions an “in-person confrontation” Madam X had with the 33-year-old female prosecutor.

She knows the make, model and color of both lovebirds’ cars. She knows the ins and outs of the love nest known as the courthouse. Cue the smiley face again as Madam X writes about the young female prosecutor.

“She put a smiley face on the continuance request. This is of significance because Judge Darnbrough was the only judge who allowed or denied the continuance requests. So she knew he would see the smiley face on the continuance request.”

At one point, the DA’s office said they couldn’t identify her because of “protection of confidentiality for witnesses to preserve future investigatory techniques.”

A few weeks later the whistleblower excuse was gone. Now, they said, it was “criminal harassment” and “the investigation” continues.

Why isn’t there more interest in this X-rated case in state-run Boston media? Again, the guy who’s locked up in North Dartmouth is a Dominican, a person of color.

There seem to be serious questions about how he ended up there, at the hands of certain unsavory Caucasian bad actors.

I thought such outrages mattered. But maybe everyone in the Bristol DA’s office and the Trial Court gets a pass because they’re all… Democrats.

Can I get me a smiley face here?

(Order Howie’s new tee shirt “Proud to be Garbage” and also get a free copy of his new book, “You Understand American?”)