Joel Caswell faces millions in fines and restitution; negotiations would bring prison time down to 42 months instead of 30 years, Times learns

More than a year after he was arrested by the FBI and indicted in April 2025 on 23 felony charges — including wire fraud, identity theft and tax evasion for defrauding federal pandemic-era programs — Jacksonville contractor and former Portland Nitro ultimate frisbee team owner Joel Matthew Caswell agreed on Tuesday to plead guilty to one-third of the charges he originally faced.

Caswell’s arrest came after a multi-year investigation following fraudulent applications for pandemic era funds intended to assist small businesses. In addition, other financial dealings included providing fraudulent information on financial applications — such as a mortgage for his Jacksonville residence — and failure to pay required taxes and other fees associated with employees for his numerous business holdings, federal prosecutors said.

Caswell, 31, was transported by U.S. Marshals to the plea hearing Tuesday afternoon, appearing in his green jail jumpsuit in U.S. District Court in Medford, where photographs aren’t permitted.

Caswell appeared before Magistrate Judge Mark D. Clarke and spoke very little other than to acknowledge his understanding of the plea deal and that he would be given credit for time served dating back to his August arrest on separate charges involving alleged drive-by shootings in Medford.

According to documents and statements made in court, Caswell has ownership and managing interests in multiple logging and construction businesses that collectively employed approximately 40 employees, according to a release by the U.S. District Attorney’s Office on Tuesday.

“Caswell was the trustee and a beneficiary of the Caswell Family Trust. From 2018 through 2022, Caswell withheld but failed to pay over trust fund taxes for multiple businesses,” the release said. “In 2019, these unpaid payroll taxes resulted in the Internal Revenue Service (IRS) assessing the Trust Fund Recovery Penalty. To evade the IRS’s ability to collect what was owed, Caswell directed customers to write checks to other companies or him personally, moved business funds, and lied to IRS collection officers.

“Separately, between 2022 and 2024, Caswell executed multiple fraud schemes in Oregon that involved submitting fabricated financial records to a bank, a private lender, and the Small Business Administration (SBA) to secure loans. Additionally, Caswell used the name, Social Security number, and date of birth of Adult Victim 1 to obtain a residential mortgage,” the release said.

In addition to charges related to his commercial entities, Caswell, who previously owned the Portland Nitro ultimate frisbee team, was also determined to have used about $70,000 of the federal funds he received to rent Providence Park in Portland for the team’s home games. Former players have alleged they weren’t getting paid and were forced to pay for their own hotel rooms and other play-related expenses.

While Caswell officially faces “up to 30 years” in prison, according to the Tuesday U.S. District Court release, legal counsel for both sides during the more than one-hour plea hearing, which the Rogue Valley Times attended, said they would agree to a 42-month prison term.

Based on the original indictment, Caswell faced four felony counts of wire fraud, three counts of tax evasion, one count of aggravated identity theft and 15 counts of failure to collect or truthfully account for and pay over tax. His plea agreement on Tuesday was reduced to eight total counts, including one count of wire fraud, three counts of tax evasion, one count of aggravated identity theft, and two counts of willful failure to pay over employment taxes.

Individually, the counts ranged from five to 30 years of prison time, but legal counsel for the government and for Caswell negotiated the 42-month proposed prison sentence, the Times was told Tuesday. As part of the plea agreement, Caswell also agreed to pay $1,198,799.83 in restitution to the IRS. He also faces a $1 million fine and five years of post-prison supervised release.

Awaiting trial on drive-by shootings

While Caswell was originally granted pre-trial release in the federal case, he has been lodged in Jackson County Jail since Aug. 27, 2025, when he was arrested in connection to a pair of shootings in northeast Medford. Medford police said the incidents — to which Caswell later pleaded not guilty — occurred July 26 and 27 in the 3600 block of Carnelian Street.

If Caswell serves a full 42 months on the federal case, for which he’ll be officially sentenced Oct. 9, he could remain in prison until March 2029. However, he awaits trial and eventual sentencing in the shooting case.

While recent months’ courtroom proceedings found Caswell’s family members in attendance, including during numerous bids by Caswell’s legal counsel for his release from jail, none were present on Tuesday at the federal courthouse in Medford.

Contacted by the Times, Caswell’s attorney, Chris Missiaen, declined to comment on the case. A message sent to Caswell’s phone, which has previously communicated with the Times, did not receieve a response on Tuesday seeking comment.

Drive-by shooting charges

Caswell is set for a pre-trial hearing June 15 in Jackson County Circuit Court on charges related to the alleged drive-by shootings. He faces two charges each: unlawful use of a weapon; recklessly endangering another person; and first-degree criminal mischief.

While originally held on $1 million bail in the shooting case, the amount was later reduced to $750,000, with bail eventually being removed, and Caswell released, due to delays in the case. He, however, remained lodged on the federal charges on a federal hold.

Former partner speaks out

Cawell’s former business partner, Tim Thompson, who attended court on Tuesday, called the plea hearing “an important step toward accountability” for Caswell, whom Thompson said is often referred to as “Teflon Joel,” alluding to dozens of unresolved civil cases and judgements against Caswell.

Thompson, who alleged he has been subjected to frivolous lawsuits by Caswell in recent years, has declined to go into detail on Caswell’s criminal charges but previously confirmed to the Times that the offices he shared with Caswell were raided by federal law enforcement in August 2022 and that he fired Caswell as the company’s timber and land manager in February 2023. Caswell was expelled from the partnership in August 2023, Thompson said.

“I was encouraged to see so many people in the courtroom standing in support of the victims. Aside from his legal team, there was no visible support for Joel,” Thompson told the Times on Tuesday.

“Hearing him plead guilty to eight federal crimes brings a measure of validation after years of uncertainty and litigation. While some may have hoped to hear a longer sentence than 42 months, the criminal case is only one part of the process,” he said. “There are still outstanding civil matters that will continue to move through the courts, and I remain committed to seeing those resolved through the legal system.”

Thompson added, “My thoughts today are with anyone who has been impacted by Joel’s actions and has waited for him to be held accountable.”

In addition to the federal and state criminal cases, Caswell was the subject of dozens of civil cases over the past decade against Caswell’s numerous business holdings registered with the Oregon Secretary of State. The cases amount to a combined millions in unpaid judgments, according to Jackson County Circuit Court records.

Reach reporter Buffy Pollock at 458-488-2029 or buffy.pollock@rv-times.com. Follow her on Twitter @orwritergal.