The man accused of ordering the death of a local rap artist in 2019 is set to begin his trial Tuesday, despite numerous complications and the man’s insistence on representing himself at trial.

Derrick Bernard, 35, is accused of ordering Aee Shawn Mathews, 26, to kill William Underwood, who went by the rapper name “FYL Jackk,” on Sept. 17, 2019.

The first of several trials between the two co-defendants is to begin Tuesday morning, and Bernard, who faces two additional attempted murder charges, is seemingly planning on representing himself pro se.

The allegations

Bernard is accused of ordering his friend and co-defendant Mathews to kill Underwood due to an ongoing online feud between the two men.

At Bernard’s preliminary hearing in May, prosecutors outlined how law enforcement investigators came to believe that Bernard had Underwood killed due to an ongoing “beef” that started on social media.

The online dispute escalated to a point where Bernard allegedly had Mathews burn down the door of an associate of Underwood’s, which led to the rap artist making a retaliatory song about the incident titled “f— you.”

Law enforcement stated during the preliminary hearing that probable cause was established to arrest Bernard and Mathews for the murder of Underwood nearly five years after it occurred due to a litany of phone calls made from the Department of Corrections by Bernard to Mathews in the lead-up to Underwood’s death and immediately after it.

At the preliminary hearings for both Bernard and Mathews, prosecutors played snippets of the recorded phone conversations where the two could be heard talking cryptically, allegedly about planning Underwood’s death.

Bernard was in custody of the Department of Corrections in 2019 at the time of Underwood’s death because he pleaded guilty to weapon possession by a previous offender in 2018, where he was sentenced to 32 months in the Department of Corrections, according to court records.

Bernard and Mathews also face an entirely separate case unrelated to Underwood’s death, where the two are facing several charges of attempted first-degree murder.

According to an arrest affidavit for Bernard, the pair are accused of shooting at two members of the Colorado Springs Police Department in a drive-by shooting in 2020.

Police allege through the affidavit that Bernard shot at the two officers in retaliation for arresting his “baby mama” for attempted first-degree murder earlier that day.

Emonie Wallace, Mathews’ sister and Bernard’s “baby mama,” was arrested in 2020 after she and Mathews shot through her neighbor’s door over a parking dispute, according to the arrest affidavit.

Court records show Wallace pleaded guilty to misdemeanor prohibited weapon use and received 24 months probation.

Mathews is alleged to have been the one who fired the weapon, and did so because he was “drunk” and “has a temper” and had a weapon at the time, according to the arrest affidavit.

Mathews is scheduled to begin trial in December on the attempted-murder charges. Bernard’s trial on the attempted murder allegations won’t start until after the homicide trial is resolved, and is currently scheduled for January.

Court chaos

Since Bernard’s arrest on attempted homicide charges in 2023, chaos has ensued in the following court hearings.

Judge Nancy Salomone is the judge overseeing Bernard’s trial. She is the ninth judge to  preside over a hearing in one of Bernard’s two criminal cases, according to court records.

Social media pages belonging to Bernard, which have remained active since his arrest, claim that nearly all the judges who have heard his case had violated his rights in various ways, with posts specifically citing frustration with “speedy trial violations.”

Those accusations on Bernard’s social media extend to his former defense attorneys as well.

At Bernard’s preliminary hearing he requested to hold a conflict hearing to have his attorney at the time fired and to represent himself pro se moving forward.

Bernard went on to clarify that he would like to be represented by an attorney, but only one who wouldn’t be “coerced” like he claims his representation from the public defender’s office has been.

At the time of writing, court records show that Bernard has no listed defense attorney.

Representing himself pro se has already led to issues in court. Judge Gregory Lammons, the previous judge overseeing the case, at the end of Bernard’s preliminary hearing shouted at Bernard over his conduct in court during the hearing.

Bernard objected to nearly every piece of evidence presented by the prosecution during the preliminary hearing, and often had verbal and physical reactions — including outright laughing — to claims being made in testimony.

Bernard’s claims 

Bernard, on social media and in direct communication with The Gazette, has alleged his innocence on all charges, describing himself as a “political prisoner” who is being detained as retaliation.

Waves of social media posts and videos on accounts belonging to Bernard claim he has been arrested to suppress knowledge he has about the Colorado Springs Police Department, and that his First Amendment rights are being violated.

At Bernard’s preliminary hearing he asked law enforcement officials directly during cross-examination if they had any knowledge or were involved in acts such as accepting bribes or covering up murders. All of these inquires were met with brief denials from the law enforcement agent being asked the question.

At one point, Bernard asked El Paso County Detective Courtney McCormack: “Ms. McCormack are you a liar and obsessed with me.”

“No,” McCormack responded.

Prosecutors have alleged throughout Bernard’s case that there is clear and overwhelming evidence of Bernard’s involvement in Underwood’s death, and there is no conspiracy.

Bernard’s trial is scheduled to begin with jury selection on Tuesday morning.

Mathews will go to trial for allegedly killing Underwood on Jan. 13. Mathews will face trial prior on the attempted homicide charges on Dec. 2.

Bernard remains in custody at the El Paso County jail on a $1.75 million bond between the two criminal cases. Mathews posted an $800,000 surety bond to be released from custody on June 11, according to court records, and remains on bond at the time of writing.