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The children playing basketball with a broken hoop stood out to Boston police Superintendent Bernard O’Rourke as he and other high-ranking police officials and community leaders walked through Roxbury’s Warren Gardens last summer.

A week later a new hoop was installed.

Police officials and civic leaders say the simple gesture is representative of the kind of officer O’Rourke is.

O’Rourke, the superintendent in charge of the Bureau of Field Services, will retire Jan. 18 after 39 years with the department. He has been described as a calm, pragmatic, no-nonsense leader who mastered the art of navigating tense situations and rallies and protests such as Occupy Boston.

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“No one is better with handling a crowd,” said Police Commissioner William B. Evans, who tapped O’Rourke in 2014 to join his command staff. “It’s a big loss for the city. I’m losing a good leader and a good friend.”

O’Rourke had aspired to be a teacher and a coach, but because those jobs were scarce , his father, a firefighter, recommended he take the civil service exam.

O’Rourke joined the Police Department in 1978, starting in Dorchester with the mounted unit before becoming a patrol officer in District D-4, which includes the Back Bay, Fenway, and the South End, and District D-14, which covers Brighton and Allston.

O’Rourke became captain in 1998 and a year later was named commander of District A-1, which includes downtown Boston, the Financial District, and Charlestown. He led the district for 12 years.

“He was the perfect example of community policing,” said Paula O’Keeffe, board member of the Beacon Hill Civic Association.

“Bernie,” as his colleagues and community leaders call him, has “a wonderful sense of humor that could defuse trouble quickly,” O’Keeffe said.

At the Veterans Day parade several years ago, antiwar protesters gathered at City Hall. O’Keeffe said a patient and courteous O’Rourke dissuaded protesters from disrupting the event.

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“He has the admirable quality of treating everyone with the utmost respect, no matter what the circumstances,” said Rosemarie Sansone, president of the Downtown Boston Improvement District.

Sansone said O’Rourke established monthly neighborhood meetings to keep residents and business owners informed on the latest happenings in the district.

“Whether it was people selling drugs or if it was making the quality of life better in developments, Bernie was always there for the people,” said Suffolk District Attorney Daniel F. Conley, who has known O’Rourke for decades. “It takes [addressing] the little things to make the city more livable.”

O’Rourke said commanding the downtown district was among his favorite roles.

In 2011, O’Rourke was promoted to deputy superintendent of the Bureau of Field Services and worked under Evans, who was leading the unit.

Evans knew O’Rourke from his South Boston neighborhood. O’Rourke grew up with Evans’s brother, Paul, and was a standout hockey player at South Boston High School, Evans said.

During Occupy Boston, O’Rourke and Evans worked together. They also worked together in 2013 when bombs exploded at the Boston Marathon.

“It was reassuring to see him out there leading some of the platoons,” Evans said.

O’Rourke said he was near the Fairmont Copley Plaza Hotel when the first bomb went off. He sprang into action and helped secure the scene and coordinate deployment.

“It was the most challenging thing I’ve ever dealt with,” O’Rourke said. “You see a lot of the bad in people and the worst things that occur in life. . . . You can’t dwell on it. You have to continue to go forward.”

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The following year, O’Rourke replaced Evans as superintendent. He is responsible for the uniform division, the Youth Violence Strike Force, the school police unit, and the bicycle unit. He is also responsible for reviewing crime trends and figuring where police should be deployed in the city.

“He’s had a long storied career,” said Patrick M. Rose, president of the Boston Police Patrolmen’s Association. “He is a well-respected leader who could be tough, but was always fair.”

O’Rourke, 63, is a married father of three adult children. He said he is looking forward to spending time with his family, fishing, and improving his golf skills after he retires.

William Ridge, O’Rourke’s second-in-command and deputy superintendent of the Bureau of Field Services, and Colm Lydon, deputy superintendent of administrative hearings, have been mentioned as possible replacements for O’Rourke. Evans confirmed that both were under consideration.

“They are two of many that could fill that position,” Evans said.

Boston police Detective Larry Ellison, president of the Massachusetts Association of Minority Law Enforcement Officers, said he would like to see someone with a “diverse background” replace O’Rourke, but if not, the next superintendent should “take into account all communities.”

The Rev. Mark V. Scott, associate pastor of Azusa Christian Community in Dorchester, agrees.

“It needs to be somebody the commissioner can rely on and trust,” Scott said. “Someone who can have the trust and confidence of the police officers and aid in continuing to build strong relationships with the community.”

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Jan Ransom can be reached at jan.ransom@globe.com. Follow her on Twitter @Jan_Ransom.