It was the first capital trial since her election in 2011, the death penalty was on the table for a heinous double murder and Mobile County District Attorney Ashley Rich prosecuted and secured the conviction herself a month after taking office.

The jury found Derrick Penn, 44 at the time, guilty on four counts of capital murder. The prosecution proved that Penn broke into the apartment of his estranged wife, Janet Penn, where he fatally shot her before beating her boyfriend to death with the same gun.

It was a strong win for a newly elected district attorney. It’s also one of a handful of capital murder convictions that have been overturned on appeal during Rich’s tenure.

In 2014, the Alabama Court of Criminal Appeals overturned Penn’s conviction and death sentence after it found “plain error” in how the jury was instructed to consider a single piece of evidence: a restraining order Janet Penn had sought for protection from her estranged husband.

The appeal was brought by the Equal Justice Initiative, a nonprofit organization that has challenged and overturned multiple capital convictions in Mobile County alone. EJI claimed the protective order was used in the original trial to imply Penn was guilty of burglary and murder because it showed his estranged wife wouldn’t have let him into her apartment willingly.

Capital murder is defined in Alabama as murder occurring during the commission of another crime. It automatically comes with potential sentences of life in prison or the death penalty. Because of that, the burglary charge was crucial to Penn’s conviction and death sentence.

However, Alabama law also prohibits using “collateral bad acts” as evidence in criminal trials because, according to EJI, “jurors tend to believe the defendant is guilty of the charged crime if he has committed previous crimes.” The higher court agreed with EJI.

While prosecutors said they intended to use the protective order to prove “motive, plan, design, scheme, [or] intent,” the appellate court found Judge Charles Graddick failed to properly limit the jury’s consideration of that evidence when he charged them.

The court also found that Rich, in her closing arguments, used the protective order to “establish what Janet [Penn] had been thinking” in the days leading up her death.

“Specifically, the prosecutor argued that the exhibit supported the State’s position that Penn had entered or remained unlawfully in Janet’s apartment, telling the jury: ‘She had filed a protection from abuse order, weeks before, because she didn’t want [Penn] around her, in her apartment, anywhere near her,” the 2014 opinion read.

For the appellate court, that was enough to call into question the validity of Penn’s convictions — the same court that overturned the 2013 capital murder conviction and death sentence of Derek Tyler Horton on similar grounds late last year.

Like Penn’s conviction, Horton’s was overturned because “collateral bad acts” were introduced to the jury including evidence that Horton has been previously investigated for an alleged domestic assault and testimony about his prior history with illegal drugs.

As has been the case with other local convictions overturned on appeal, the fly in the ointment was a procedural issue, as in the case against Carlos Kennedy, whose 2013 conviction and death sentence for sexually assaulting a 69-year-old Mobile woman before beating her to death with a clawhammer was overturned because he wasn’t allowed to act his own attorney at trial.

Last year, Kennedy was given that chance during a lengthy retrial. However, Kennedy called no witnesses and presented no evidence and, for the second time, was found guilty of capital murder, though he dodged a death sentence after the jury instead recommended life without parole.

For the second time, Derrick Shawn Penn was convicted and sentenced to death for the 2009 murder of his estranged wife and her boyfriend. (Mobile Metro Jail)

Penn’s retrial last week also ended with a second unanimous guilty verdict following a brief day of deliberation. On Tuesday morning, the jury returned an 11-1 recommendation in favor of the death penalty to Judge Rick Stout.

As in the first trial, Penn never denied killing his wife and her new boyfriend. Instead, seeking a lesser charge, the defense argued that Penn hadn’t broken into his wife’s apartment that night in 2009, and that the killings were not premeditated but done in the “heat of passion.”

His second prosecution, led by Assistant District Attorney Jennifer Wright, argued Penn betrayed that defense with his own words in statements captured on a series of voicemail messages left for Janet Penn in the weeks leading up to her murder.

“They want you to believe that it was all in the sudden heat of passion but his own words tell you what he was going to do,” Wright said during closing arguments. “This isn’t something he just said one time. There were threats and multiple statements that he was going to kill them.”

Specifically, those messages recorded Penn saying things like “You’re going to make me kill y’all” and that if “he couldn’t have [Janet], no one could.”

However, the petition for protection from abuse that Janet Penn filed a few weeks prior to her death was referenced again during the retrial. During her closing arguments, Wright referenced it to show that Janet had made attempts “to keep him away from her” and “wasn’t trying to get back together with him,” as the defense had alluded.

While it’s unclear how that reference to the document might be viewed during an appellate review, any decision as to its appropriateness would be based on how Judge Stout instructed the jury to consider that evidence before they were sent into deliberations.

If for any reason Penn appeals his new conviction and sentence, it will require the court of criminal appeals to check for any “plain error or defect in the proceedings,” which is required in all cases where the death penalty is imposed regardless of the reasons for the appeal.