For years, Joseph Gillespie lived something of a double life.
At home, friends and loved ones said, he was a devoted spouse and father, overcoming childhood trauma and channeling his energy into the next generation as a high school football coach.
At work, according to federal prosecutors, Gillespie harbored different motivations. The former Baltimore City government employee admitted last year to accepting cash bribes to adjust homeowners’ tax and water liens over nearly a decade. He was sentenced Thursday to five years in prison with one year suspended for his conduct as well as for his involvement in a separate case for which he was charged. He was also ordered to pay restitution and spend three years on supervised probation.
The sentence was at the top of the range that Gillespie, 35, agreed to when he reached a plea deal with prosecutors in August. His attorneys had asked for two years, but the request was denied by U.S. District Judge Richard D. Bennett, who repeatedly expressed disappointment with Gillespie’s conduct.
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“It’s a very sad day in Baltimore City, in my opinion,” Bennett said at Thursday’s sentencing. “They [students] looked up to this man and he conducted himself as an absolute thief.”
Members of Gillespie’s inner circle at times broke into tears and left the room during the hearing. Some lowered their heads and held their hands in prayer as the judge imposed the sentence.
The case blew open last year when Gillespie pleaded guilty to wire fraud conspiracy in a separate case centering on COVID-19 relief funds. Gillespie lied to get approved for a $143,000 loan and laundered it to a fake payroll to get it forgiven. As part of the plea deal, Gillespie, who worked for the city Department of Finance‘s revenue collections division, acknowledged the bribery scheme, which the FBI had been tracking since 2016. In court filings, federal prosecutors said Gillespie cost the city $1.25 million in losses and made around $250,000 in profits from the scheme.
“He abused his position of trust for nearly a decade,” Assistant U.S. Attorney Paul Riley said at Thursday’s hearing. “This was a deliberate, longstanding pattern of corruption: brazen, bold.”
The Gillespie case has prompted questions about Baltimore’s back-end systems and how an employee could execute a bribery scheme undetected for so long. It also left some unanswered questions — including about Gillespie’s alleged accomplice in the Department of Public Works, whom prosecutors referenced on Thursday but have not identified.
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Federal prosecutors said in a February sentencing memo that Gillespie’s ruse started in early 2016 and continued until his arrest on Sept. 20, 2023. They said Gillespie “routinely” accepted bribes from property owners to either remove liens completely or delay payment due dates. At times, he helped some homeowners avoid the annual tax sale, a process by which the city can recover debts but which can also cost residents their homes if they don’t pay it off in time.
Undercover FBI agents helped expose the scheme. In a recorded phone conversation that was played Thursday in court, an agent asked Gillespie if he wanted $100 for each property for which he could push back the due date.
“Yeah, that’s basically how I do,” Gillespie said. He told the agent he had a “girl” in “Water” — shorthand for Baltimore’s public works agency — who could “wipe some shit out” and remove the financial obligation owed to the city. He also referenced a retired accomplice whom he had previously colluded with and said he hoped to loop in a state-level employee as his “next goal.”
In a separate video recording, Gillespie told the agent that he had the ability to mark an owed amount as paid, even if the money had not been received. “There was a couple, extra miscellaneous bills y’all had that I wiped off,” he said. “That shit gone now.” He also pushed back the due date for debts on eight properties by three months.
After watching the eight-minute tape, the judge asked the team of federal prosecutors and FBI agents why it had taken so long to bring charges against Gillespie.
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“The right arm doesn’t know what the left is doing,” said Bennett, who expressed frustration over the unchecked continuity, and the rising expense to taxpayers, of the bribery scheme during that period. “What if you had waited 20 years?”
Riley, the federal prosecutor, said the team moved on the previously “closed and inactive” case as soon as the wire fraud matter came to light and couldn’t speak to why it had gone dark. He said investigators uncovered files from Gillespie’s iCloud account showing communications among him and “numerous” individuals he involved in the scheme.
Later, Bennett acknowledged that investigations can take time.
He also took note of the nearly two dozen Gillespie supporters who crowded onto courtroom benches Thursday, as well as the many who wrote letters or signed petitions attesting to the defendant’s character and asking the judge for compassion.
In a statement Thursday, Gillespie apologized and said he would not “sugarcoat” the severity of his crimes to his football team at Carver Vocational Technical High School. He said he had become frustrated by city policies that enabled some homeowners to lose their properties in the tax sale without much transparency.
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“I should’ve left the city a long time ago,” Gillespie said. “Some practices I disagreed with and I tried to fix it myself. I just took it way too far.”
The judge shot back that if that were true, Gillespie wouldn’t have needed to line his own pockets.
“You took money because it was greedy,” the judge said. “What makes it worse is that young people look up to you, young men in an impressionable state of mind. That makes it an extra disappointment.”
“I respect that,” Gillespie replied.
The mother of one of Gillespie’s former athletes appeared at the federal courthouse on Thursday and told the judge how much Gillespie had meant to her family.
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Her son, now a high school sophomore, experienced abuse as a boy and had long struggled to open up. Then, she said, he met “Coach Joe,” and her son’s demeanor changed.
“It meant the world to me,” she said.
Gillespie had talked to her son about playing baseball in the spring and attending college, she said, and had even been a support system for her.
Bennett said Gillespie’s positive influence on others went into his sentencing decision. He encouraged Gillespie to serve his time, put it behind him and then try to more forward.
“It’s very disappointing,” the judge said. “But I think you’ll come back from this.”
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