It’s only February, but we may already have our winner in the “Failing Upwards” contest for 2022.
Yesterday, the Broward County School Board in Fort Lauderdale voted 7-2 to make Vickie Cartwright their new superintendent. If that name sounds familiar, it’s because until last year, Cartwright was the superintendent of the Oshkosh Area School District–and to many of those working under her in Oshkosh, yesterday’s announcement likely came as a huge surprise.
For those who weren’t following closely, Cartwright resigned after principals and other administrators in Oshkosh started bringing anonymous complaints about her to the School Board. Those complaints included: belittling the work of principals, making most decisions unilaterally, ignoring the input of her principals and administrators, creating a culture where speaking up was discouraged, and endlessly comparing programs here to how things were done in her previous position: Administrator of Orange County Schools–which is the Orlando area. All of that resulted in a contentious closed-door School Board meeting after which members chided the administrators for being secretive about their complaints–but jointly read a stilted public statement that they were going to be more closely-monitoring Cartwright’s performance. A couple of months after that–she tendered her resignation and all but stopped coming to work.
Why Cartwright came from Orlando to Oshkosh in 2018 was never really fleshed out, even after three years in the Fox Valley. In my interviews with her as a candidate for the position and eventually as Superintendent she spoke generally of looking for new opportunities and a new culture. I always got a Coach Norman Dale from the movie Hoosiers kind of vibe–where a once high-profile college basketball coach loses his job for punching a player and is forced to take a job in rural Indiana to start rebuilding his reputation. So I really wasn’t that surprised when just a couple of months after her resignation in Oshkosh she was hired as the Interim Superintendent in Broward County after their previous superintendent resigned following criminal charges of perjury being filed against him.
What did surprise me is a few weeks into the new gig, I saw Cartwright on the cable news networks getting national attention for challenging Florida Governor Ron DeSantis’ order that schools drop their mask mandates. Cartwright was being hailed as a “hero” for ordering her students and staff to mask up.
Before yesterday’s vote, one man, a Trumpkin by the name of Chris Paul, addressed the Broward County School Board and read off the results of an internal Oshkosh School District survey of administrators and principals that spelled out their overwhelming dissatisfaction with Cartwright’s performance up here. His questions about whether the Board had considered that survey and if they expect vastly different results from Cartwright in one of the largest school district’s in the country were met with stony silence. When the same guy went up and asked Cartwright herself about the survey–with his cellphone camera rolling of course–he was pushed away by security.
So how did someone who so spectacularly failed as a leader in Oshkosh become the choice for a district 27-times larger? For starters, her competition in the final two was a retired Air Force officer whose only teaching experience was flight training, and who had been working as a consultant in educational leadership. Not exactly a resume that screams “leader in the field of primary education”. It should also be noted that the School Board in naming Cartwright the interim superintendent explicitly stated that she would not be eligible to apply for the position on a permanent basis–but then reneged on that policy. But it was in a comment that School Board President Laurie Rich Levinson provided to Local 10 TV after the vote that the real explanation may have been found: “This is monumental for the district. We have our first female superintendent!”
It might be unfair to joke about the quality of education in the southern parts of the US, or point out that the region does have its own culture and attitude toward doing good work. But I’d like to think that we are better off here in “little ol’ Wisconsin” expecting more for our kids and those that teach them.




