Sterling, a big-name donor, made contributions that helped earn him NAACP awards as he tried to recover from a damaging discrimination lawsuit. Jenkins, the LA chapter's president, sought to use his volunteer work to show he was ready to return to practicing law after having been disbarred.
But in the days since racist comments from the NBA team owner became public, both men have fallen further and tarnished the organization that brought them together.
"We do have this society that gives people an out by allowing them to redeem themselves through charity," Daniel Borochoff, president of CharityWatch, said. "And that's something that can be worth it — if it doesn't destroy the integrity of the organization."
This month, Sterling was to receive a lifetime achievement award from the local civil rights group at its 100th anniversary celebration. But Jenkins revoked the honor after a private conversation became public and Sterling was heard admonishing a female acquaintance to hide her association with blacks and "don't bring them to my games."
Jenkins' response wasn't enough to quell the backlash, and he stepped down Thursday "to separate the Los Angeles NAACP and the NAACP from the negative exposure I have caused."
The national civil rights group acknowledges harm from the situation but says local branches operate independently. Area chapters don't run decisions by the national organization any more than city mayors consult with the U.S. president, NAACP national spokesman Derek Turner said.
Still, in announcing Jenkins' resignation, the national NAACP said it would set guidelines to help branches select awardees. "Clearly, there was a need for better vetting in this situation," Turner said. "So that's a major concern for us."
Sterling has not commented on the controversy, which has cost him a $2.5 million fine and a lifetime ban from the team and league.
Jenkins could not be reached for comment Friday. Calls and emails to the Los Angeles chapter were not returned.
Sterling and Jenkins have known each other at least since 2009, when the business magnate was honored by the new leader of the Los Angeles chapter of the National Association for the Advancement of Colored People. It was the same year Sterling agreed to pay $2.7 million to settle federal charges that he refused to rent apartments to blacks and Hispanics.
Sterling had been honored for donating to minority charities and giving game tickets to inner-city children, Jenkins said.
The Donald T. Sterling Charitable Foundation gave $5,000 to the NAACP's Los Angeles chapter in 2010, according to tax records. There was no record of contributions in other years.
Jenkins' resignation represents a second major public setback.
More than 25 years ago, federal prosecutors charged Jenkins, then a young Michigan judge, with extortion and racketeering conspiracy. Authorities said he requested and received money, jewelry, a handgun and other gifts to dismiss traffic tickets and other misdemeanors.
Jenkins was acquitted after two trials, but in 1991 the Michigan Supreme Court removed him from the bench, saying he "systematically and routinely sold his office and his public trust." Michigan and California subsequently banned him from practicing law.
He has sought reinstatement, citing his volunteer work with the NAACP and others as proof of his turnaround, according to state bar case documents.
Though he has "impressive good character evidence and community service," three judges with the California State Bar Court wrote last month, Jenkins "continues to commit errors in judgment that call into question his rehabilitation and present good moral character."
The judges said he misrepresented his finances or other aspects of his personal life in several instances. They denied his most recent reinstatement request.
In the local civil rights community, Jenkins has a reputation as a behind-the-scenes negotiator.
"Some of our people wanted to be radical but he was more measured," said Dwayne Wyatt, a city employee who has worked with him on countering discrimination in the city's planning department. "Some people have felt he may have a little bit too cautious, but I didn't think so."
Jenkins didn't have a high-profile with the national group, which has more than 200,000 members.
The LA chapter has nearly 1,300 members and bears the name of the nation's second-largest city, but it's not the most prominent area chapter. That distinction goes to Beverly Hills/Hollywood chapter, which is known for honoring diversity in film, television and music with its annual Image Awards.
Several LA-area activists outside the NAACP said they liked the third-term chapter president and that he had done important work. They also said they had been unaware of his previous legal problems.
"I would never have guessed that from the interactions I had with him over the course of time," said Adrian Dove, chairman of the Congress of Racial Equality.
Dove said Jenkins' past doesn't change his view of the man's work in Los Angeles, but some disagree.
"A reasonable person has to ask," said community activist Earl Ofari Hutchinson, "'What does this say about the integrity that he brought to the organization?'"
Associated Press writer Ed White in Detroit and researcher Rhonda Shafner in New York contributed to this report.
Contact Justin Pritchard at https://twitter.com/lalanewsman