Next week, Kennedy faces something he hasn't seen in nearly 75 years: an election in which he's not on the ballot.
At age 96, the Democrat is leaving public office. The decision is less about his heart than his stamina.
"The walker," Kennedy said, pointing to the ambulatory device his relatives forced him to buy, "told me it was time to retire."
He spoke last week as he sat in the South Coatesville house he built a half-century ago - in a comfortable green armchair near his phone and notepad, where he keeps pages and pages of names and numbers handy.
The walls and shelves around him were stocked with plaques and awards. He rummaged through a plastic bag full of certificates honoring his service, including a citation from the Pennsylvania Senate.
"I have plaques I've never even taken out of the box," Kennedy said.
A thin man with wisps of white hair and fewer wrinkles than one might expect, Kennedy remains among the few living witnesses to decades of transformation in that part of Chester County. He's also seen how things can remain the same.
The mayor said he was shocked to hear that former School Superintendent Richard Como exchanged racist and sexist text messages about students and staff with another school official, leading to the administrators' resignations last month. He and Como used to talk at meetings and parties, Kennedy said.
"I never dreamed the man thought like that about us, about me," he said.
Kennedy's job duties as mayor for five terms included keeping order in the town of about 1,300, securing grants, and declaring snow emergencies. He also oversaw the Police Department and hired the town's first female police officer early in his tenure.
He said he still wishes he had more time to build a new police station and borough hall, plans that are still in the works.
"The fight's over," he said. "I'm too old."
Despite his age, Kennedy still goes to council meetings and borough events. A few weeks ago, he wanted to get a document from his mailbox at Borough Hall during a heavy rainstorm.
He asked his neighbor Councilwoman Sylvia Washington to drive him there. Washington eventually talked him out of going. He's dedicated and trustworthy, which is why residents kept electing him, said Washington, who views him as a mentor. And his mind is still sharp.
"He can cite regulations. And you're not going to pull nothing over on him, that's for sure," she said.
Borough Council President Bill Henson said Kennedy's knowledge of the area and its history had been valuable to the local government through the years. And one of Kennedy's strengths is his ability to get people to work together and remember their responsibility to the public, Henson said.
"I would put him up against any small-town mayor anywhere," he said.
South Coatesville has already dedicated a park near his house and named a street after him. Asked how he felt about the honors, Kennedy said simply, "It didn't bother me."
The town will miss him as mayor, said Councilman John Washington, one of three candidates running for Kennedy's seat. "But he's not really going to retire, because we're still going to be picking his mind."
Washington, John D. Long Jr., and James Marino will face off next week. Kennedy said he didn't know whom he would vote for; he is friends with Washington and Long.
Long and Marino said they had a better shot of winning now that they don't have to run against Kennedy.
BY THE NUMBERS
Jim Kennedy's age
Number of terms he served as mayor of South Coatesville
His years in public service
Award plaques in his back room