Bob Raines, the superintendent who oversaw a tumultuous five-year period at West Marin’s largest school district, will retire at the end of the school year. Since 2016, Mr. Raines has helmed the Shoreline Unified School District as principals have come and gone, staff have decried improper labor practices and a critical budget officer position sat unfilled for almost two years. He will leave behind a more stable district: The three current principals have shown leadership and commitment, employees are enjoying an era of labor peace, and the new budget officer, Logan Martin, has shored up operations at the district office. “Where I am in my arc, it’s a good time to step away and turn the keys over to someone else and say, ‘Go out and do some really good stuff now, because it’s all in place to do,’” Mr. Raines said. “Whoever comes in and takes my spot is going to join a really strong team.” His retirement, effective June 30, 2021, will end a 43-year career in California public education as a teacher, a principal and a superintendent, including a two-year stint as the head of West Marin School in the late ‘80s. Mr. Raines said that no year compared to this one, when campuses closed due to Covid-19 and the district’s 500 students shifted to distance learning. The year has been full of stops and starts, changing edicts and on-the-go adaptations. Teachers are adjusting to the new method of delivering instruction and support staff are distributing lunches and devices, all while Mr. Raines leads a team planning a safe return to in-person instruction. Although classrooms are now allowed to open in Marin, Mr. Raines has not set a reopening date; the shift will create a lot of work for teachers, and the district is still finalizing its site-specific protection plans. At Shoreline, Mr. Raines has made equity a central piece of his mission, but the challenge of closing the achievement gap is formidable: In the latest round of standardized testing, 68 percent of white students and 27 percent of Latino students at Shoreline passed the English and language arts assessment, while 46 percent of white students and 16 percent of Latino students met standards in math. Distance learning is exacerbating the gap, as students with poor internet, crowded homes and familial responsibility struggle to access virtual instruction. Shoreline is working to address the issues, Mr. Raines said, including by opening learning hubs at Tomales Elementary and West Marin Schools. “It’s not that anybody is unaware of the challenges many of our kids have,” he said. The greatest conflict in Mr. Raines’s tenure was with Matt Nagle, a middle school principal who was demoted to elementary school teacher in 2018. Parents signed a petition declaring a vote of no confidence in Mr. Raines for his lack of transparency and engagement around the decision, and Mr. Nagle sued the district for defamation and retaliation. The principal showed up to every board meeting to criticize Mr. Raines, until ultimately the district settled with him for $700,000 and his resignation in February. Among his accomplishments, Mr. Raines pointed to facilities improvements at all campuses, financed by voter-approved bonds. Long-term issues with old buildings are being addressed. In retirement, Mr. Raines said he is still motivated to support schools in some way, particularly around building leaders that look like their communities. He turns 67 next summer and is hoping to spend more time with his sons and 10-month-old granddaughter in Colorado. “I’m not going to be sitting in my garage carving wood,” he joked.