She won the appointment to Baltimore state's attorney that he wanted in 1995. Later, as mayor, he famously called for her to "get off her ass" and prosecute a case. She said he was "hoodwinking" the public into thinking his crime-fighting strategies were effective.
And in one of his last acts before leaving the city, he raised the salary for her office by tens of thousands of dollars, in what many viewed as an attempt to make the position more attractive to challengers.
But now Gov. Martin O'Malley and Baltimore State's Attorney Patricia Jessamy — Democrats both locked in re-election fights — appear to be setting aside their differences. Appearing Thursday in West Baltimore, O'Malley sang the prosecutor's praises — and hinted at a forthcoming endorsement.
"They say politics makes strange bedfellows," said Gary McLhinney, the longtime city police union president. "Well, this is about as strange as it gets."
O'Malley, deadlocked in the polls with Republican former Gov. Robert L. Ehrlich Jr., appeared with Mayor Stephanie Rawlings-Blake, Police Commissioner Frederick H. Bealefeld III and others to announce $7 million in public safety grants for the city.
The event followed the fatal stabbing of a young Johns Hopkins researcher Sunday night as he walked from Penn Station to his home in Charles Village, which has sparked renewed criticism of the court system.
O'Malley was asked whether he would support a candidate in the Democratic primary for state's attorney. Defense attorney Gregg Bernstein, a former federal prosecutor, is leading the first primary challenge against Jessamy in eight years.
"We've done a lot of positive things together," O'Malley said. "I believe the state's attorney's office, led by Mrs. Jessamy, has had a significant part in saving lives. It would fly in the face of the facts to say it hasn't."
Asked specifically whether he was endorsing Jessamy, O'Malley replied: "Yeah, stay tuned. Partnerships between the state and the state's attorney's office have never been stronger."
His support might take the form of more than just words. Lt. Gov. Anthony G. Brown reportedly attended a birthday fundraiser for Jessamy over the weekend.
Johns Hopkins University political scientist Matthew Crenson says O'Malley may be trying to maximize his support in the African-American community, where Jessamy remains popular. Crenson said O'Malley is losing among white voters.
"The governor's unquestionably in trouble, and his success depends critically not just on black support, but on significant black turnout," Crenson said.
When Bernstein announced his plans to run, Jessamy told The Baltimore Sun that she believed O'Malley had put him up to it. On Thursday, Bernstein called any apparent alliance between O'Malley and Jessamy "irrelevant."
"What's relevant to the citizens of Baltimore is whether they feel safer and whether they feel safer and whether violent criminals, like the ones who murdered poor [Hopkins researcher] Stephen Pitcairn, are being locked up," he said.
Steve Levin, an attorney who is supporting Bernstein but not O'Malley, said that "it simply doesn't make sense that he would be supporting someone who's been as ineffective as she has."
"His timing is curious, his judgment is terrible, and I think it's pure politics," Levin said.
An O'Malley campaign spokesman stressed that the governor had not formally endorsed either candidate — and said he has no plans to.
The important thing, spokesman Rick Abbruzzese said, "is that the two of them are working well together and achieving results."
O'Malley and Jessamy have both made city crime declines a key part of their re-election campaigns. O'Malley has taken a tough-on-crime mantra to the governor's office, where he says he has forged stronger partnerships between state and city law enforcement agencies. According to O'Malley, the state's violent crime rate is at its lowest point since at least 1975.
As Jessamy's critics question her over conviction rates, she and her supporters have been pushing the city's overall crime declines during her 15-year tenure — and saying she's been the only constant.
Jessamy declined to comment on O'Malley's remarks. But a spokeswoman also highlighted programs on which their offices had worked together.
In praising Jessamy on Thursday, O'Malley spoke repeatedly of "historic" crime declines over the past decade, and said the state's attorney's office had been a crucial partner — "notwithstanding some occasional disagreements."
Critics say their public feud slowed progress against crime and led to dysfunction. Jessamy was a chief detractor of O'Malley's "zero tolerance" policing model and has repeatedly praised subsequent administrations for moving away from it.
Edward T. Norris, who was police commissioner during the height of their dispute, said that "every day was an adventure" and that the sparring drove a wedge between the Police Department and the state's attorney's office that remains today.
McLhinney said he didn't know what to make of O'Malley's "change of heart in an election year."
"But the fact is Pat Jessamy has been a disaster in Baltimore City, and you'd be hard-pressed to find a single law enforcement professional who thinks she's doing a good job."
Crenson said the public has a short memory. The average voter, he said, is not likely to view an endorsement as a shift in position or political opportunism.
Del. Curt Anderson, a Baltimore Democrat and chair of the city delegation to Annapolis, said O'Malley and Jessamy both are fiery, sometimes stubborn leaders whose history was well-documented. But Anderson said he's personally never seen any animosity between them.
"I won't say I'm shocked, but I'll say it's interesting to find the governor has supported her," Anderson said.