State Sen. Joan Carter Conway was one of a handful of people who stood beside Martin O'Malley on the corner of Harford Road and The Alameda in June 1999 when the Baltimore City councilman announced his bid for mayor.

She played an important role in his election, as the first African-American elected official to endorse the white candidate for mayor in this majority-black city.

But 3 1/2 years later, she's one of his most outspoken critics and is considering a run against him in the Democratic primary.

Why their relationship deteriorated is in dispute. Her allies claim O'Malley used her for political gain and then stopped listening to her once he was elected. Officials at City Hall say Conway pushed the mayor too far by trying to strong-arm him into hiring people she recommended and playing the kind of old-style patronage politics he campaigned against.

Whatever the reason, their falling-out shows the fragility of friendships in the rough arena of city politics.

The rupture could play a role in the next mayor's race in much the same way that a split between O'Malley and former City Council President Lawrence A. Bell III was central to the 1999 mayoral primary, when O'Malley ran against and beat his former friend.

"No, I'm not that happy with this administration. ... There seems to be an arrogance about this administration," said Conway, a former City Council member.

"Martin campaigned on neighborhoods first, and I don't think he has put neighborhoods first. He has spent too much time on law enforcement and neglected other areas like parks and recreation, public works, picking up trash, and boarding and renovating housing," she said.

Conway said some of her supporters are urging her to run against O'Malley. "I have not yet made any commitments about whether I will run or not," she said.

O'Malley said he's grateful to Conway for backing his campaign and helping his administration obtain more state funding for drug treatment and schools.

"I don't really know the source of her discontent," O'Malley said. "I'm sorry that for whatever reason she's unable to take any personal satisfaction in the successes of this administration."

A few people, including City Councilman Kenneth N. Harris Sr., say they've tried to work as peacemakers.

"There has definitely been a falling-out between the two of them," Harris said. "At one point, I tried to get them together to iron out their differences. But that didn't work, and I didn't want to end up as the referee punched in the middle of two heavyweights."

The volatile relationship between O'Malley and Conway dates to 1993 when she was a blunt-spoken, sometimes-emotional 42-year-old director of a city social services center in Northeast Baltimore.

O'Malley was a 30-year-old lawyer and Irish rock singer who had earned a reputation as a firebrand since his election to the council two years earlier.

The two marched together to protest crime in the Govans neighborhood. And two years later, they ran on the same City Council ticket.

At the time, no African-American had ever been elected to represent the council's 3rd District in Northeast Baltimore.

But O'Malley and Conway formed a partnership and ran on a ticket with O'Malley's uncle-in-law, Robert W. Curran, whose family had been influential in Northeast Baltimore politics for decades.

Conway, O'Malley and Curran were brought together by Doris M. Johnson, a Democratic Party activist and former member of the city Elections Board.

Johnson saw in Conway the political skills and dynamic personality needed to break through the color barrier in the district, according to people who knew Johnson, who died in 1999.

"Doris had a way of getting people together," said Rita R. Church, a former 3rd District councilwoman. "And Doris thought it would be a good team because O'Malley needed support from the black people, and Joan needed the support of the white constituents."

Conway, O'Malley and Curran all won that November. Conway and O'Malley became close friends, with O'Malley once serving as Conway's lawyer to help her out of a minor police dispute. But the two have had a hot-and-cold relationship because they are both emotional people with sometimes clashing allegiances and ideas about how to run government, according to people who know them.

"They are both very similar," Church said. "They are both very outspoken, very stubborn. ... And they have both made very good politicians."

Conway conceded that "we both have strong personalities. Our energy levels, our emotions, run high sometimes."

The two have helped each other politically. When Sen. John A. Pica Jr. resigned in 1997, O'Malley supported Conway's efforts to be named Pica's replacement by the district's Democratic Central Committee. This made her the first black senator, and the first woman, to represent the 43rd District.

In turn, when O'Malley ran for mayor two years later, Conway was the first African-American lawmaker to endorse him. She took some abuse for this, including being publicly called a "pseudo-Negro" by Julius C. Henson, a consultant to Bell.

"Senator Conway showed a lot of courage supporting O'Malley very early - and she was instrumental, if not critical, in his victory," Pica said.

Conway embraced O'Malley during his victory party in 1999. But she said that afterward there was a "power struggle" within the O'Malley camp over who would help lead the transition team, Conway or Del. Howard P. Rawlings. In the end, O'Malley went with two others as co-chairmen.

O'Malley followed Conway's advice in picking George Winfield as director of the Department of Public Works. But the mayor didn't listen to her in choosing New York City police commander Edward T. Norris to head Baltimore's Police Department. She wanted Deputy Commissioner Barry W. Powell.

And she later tried unsuccessfully to influence a number of other personnel decisions in police and housing, according to City Hall officials.

"Joan had some people she wanted to have employed, and Martin tried. But some of her people worked out and some didn't - and there could have been some animosity there," said Del. Ann Marie Doory, who knows them both.

Conway also made O'Malley uncomfortable in October 2000 when she pressured him to give more money to the politically connected family of strip club manager Kenneth Jackson, a convicted felon, as compensation for moving the family's El Dorado Lounge for a city redevelopment project, according to a City Hall official.

In January 2001, Conway took the floor of the Senate to publicly demand an apology from O'Malley for aiming a curse-laden diatribe against State's Attorney Patricia C. Jessamy after she dropped charges in a police corruption case.

Curran said Conway put O'Malley in an awkward position by making so many requests of the mayor.

"Do you follow through with a grocery list of things? You look at each one and decide if it's good for the city," said Curran. "Nobody controls Martin O'Malley, which is good because you're not beholden to anybody."

Conway denies that she's angry at O'Malley because he didn't follow her advice.

"I'm not asking him to be beholden to me," Conway said.

She said she's critical because voters tell her O'Malley hasn't followed through with promises to provide better services. And she said it doesn't make sense that O'Malley has appointed so many people to leadership positions who are young and don't know the city.

"Martin does not have an easy job. Managing the city is very difficult," Conway said. "But when you don't have people around you with wisdom, with a few gray hairs, you tend to make a lot of problems."