2020

President Winfrey? Here’s what we know about Oprah’s education outlook

Oprah Winfrey, right, hosted N.J. Gov. Chris Christie, Newark Mayor Cory Booker, and Facebook founder Mark Zuckerberg when Zuckerberg announced a $100 million gift to Newark schools in 2010.

When Oprah Winfrey delivered an emotional, inspirational speech at the Golden Globes on Sunday, many viewed it as an introductory address for a possible presidential run.

Indeed, after years of denying any political ambitions, people close to Winfrey now say she’s open to running for office, according to CNN. (She again denied plans to run on Monday.)

So what would a President Winfrey look like when it comes to education? As with most policy issues, she hasn’t taken a firm stand — but her background, personal giving, and guests on her show, which aired from 1986 until 2011, all offer clues. Here’s what we know.

She understands racism and poverty in America — and how schools can make a difference.

Growing up impoverished in the South and then Milwaukee, Winfrey endured many of the challenges that disproportionately affect poor children in America, including family instability, teen pregnancy, and frequent school changes. (She was also sexually abused by family members.) She credits a fourth-grade teacher with giving her the intellectual energy to persevere.

“I always, because of you, felt I could take on the world,” Winfrey said in a 1989 special where she honored her favorite teachers. “You did exactly what teachers are supposed to do. They create a spark for learning that lives with you from then on.”

As a teenager, Winfrey did so well at her Milwaukee high school that a teacher decided to help her become one of 16 black students to integrate a high school in an affluent suburb. (She later left that school when her mother decided to send her to Nashville, where she also attended a newly integrated high school.) “It was culture shock for me. It was the first time I realized I was poor,” she said during the 1989 show. “But it made a major difference in my life.”

Those experiences left Winfrey believing in the power of schools to change lives, she has said. “I value nothing more in the world than education,” Winfrey said in 2010. “It is the reason why I can stand here today. It is an open door to freedom.”

She has given to education initiatives that cross partisan divides.

As one of the world’s wealthiest women, with a net worth of nearly $3 billion, Winfrey has directed her giving to a wide array of causes, including education. She has donated to charter schools across the country, participated in a collective to reduce high school dropouts, and funded scholarships for students at historically black colleges.

She even launched a school of her own in South Africa that has sent poor girls to elite universities. For a megastar, Winfrey took an unusually personal role in the school’s development: She handpicked the school’s first class; overhauled the leadership when a sex abuse scandal occurred early on; gave students her personal cell phone number; and took the first graduates shopping for dorm-room decor.

The experience gave Winfrey insights into what kinds of efforts might alter the track of poor students’ lives. “I had worked with other organizations, I had written lots of checks, I had started my own big sister program, where I was taking girls on skiing trips and spending time with them and reading. It doesn’t work,” she said in 2017.

“What works is being able to change the trajectory of somebody’s life where you are literally brainwashing them for the good,” Winfrey added, as she reflected on her school’s first decade. “Because what poverty does is brainwashes you to believe that you are not enough.”

She’s also aligned herself with heavyweights of the ‘education reform’ movement.

Many people treated Winfrey’s enormously popular show as an ideal platform to reach Americans of all races and classes — something that can be especially pressing for education influencers, who are often criticized for imposing their ideas on poor communities.

Toward the end of the show’s run, Facebook founder Mark Zuckerberg chose it to announce a $100 million gift to overhaul schools in Newark, New Jersey. Also on that episode: then-New Jersey Gov. Chris Christie and then-Newark Mayor Cory Booker, now U.S. senator. The trio, Winfrey said, “are putting politics aside to help turn around the failing public schools in Newark.”

One of the most education policy-heavy episodes of Winfrey’s show aired in 2010, when Winfrey promoted the documentary “Waiting for Superman” with a special about “the shocking state of our schools.”

The film galvanized support for charter schools, and teachers unions treated it as an attack. Winfrey gave air time to the director, Davis Guggenheim, as well as to philanthropist Bill Gates and Michelle Rhee, then the Washington D.C. schools chief who was attracting attention for trying to fire low-performing teachers.

Winfrey called Rhee “a warrior woman” and appeared sympathetic to Rhee’s agenda, at one point asking her, “Why can’t you just fire bad teachers?” But Winfrey also hit some more positive notes.

“Everybody knows I love good teachers, and there are so many thousands of you — great ones — in this country,” Winfrey said on the show. “So we’re not talking about you if you are a good teacher.”

As part of the episode, Winfrey capped off a round of giving from her Angel Network philanthropy with $1 million awards to six networks of charter schools, which she suggested were making almost superhuman efforts to help their students.

“Imagine this,” Winfrey said. “A school where high school freshmen, reading at a fourth-grade level, can jump ahead five grades in a single school year. Or a school where teachers stay until 11 at night to help children with their homework, and where children say school is like a second family to them.”

Winfrey’s proclivity to promote heroes sometimes resulted in unstable education initiatives getting a boost: One New Orleans charter school that the Oprah Winfrey Network profiled as a promising turnaround effort closed a year later as one of the lowest-performing schools in Louisiana. And Zuckerberg’s Newark donation, which spurred a controversial package of policy changes for Newark schools, had mixed results: Growth in student achievement dropped for three years, but bounced back in years four and five.

Have her views shifted as many in the Democratic party have shifted their education outlook? We don’t know.

One of Winfrey’s most sustained causes has been Booker, whose U.S. Senate race she supported with fundraising and air time.

Booker’s personal evolution on education issues reflects a broader one within the Democratic party. Early in his career, Booker became known for championing charter schools and sat on the board of Democrats for Education Reform, a group that set out to counter the influence of teachers unions in local elections. But as uneven results and pushback from local communities have racked up, Booker puts less emphasis on the most divisive parts of that agenda. Now, he is more likely to promote pre-kindergarten and criticize Donald Trump’s education secretary, Betsy DeVos, than to propose particular policies to improve schools.

That mirrors a broader shift in the education world. Gates, for example, has turned away from funding individual schools and policy initiatives in favor of supporting locally led efforts to improve education.

It’s unclear whether Winfrey is attuned to this shift: Since her show went off the air, Winfrey hasn’t often commented publicly on major matters of public debate, including education issues — although she did endorse Hillary Clinton for president in 2016, and expressed disbelief that Donald Trump, like her an entertainer, had been elected instead. (Trump’s nomination, she said at the time, made her feel for the first time “really qualified” to run for office.)

Her speech at the Golden Globes — which focused on empowering women — suggests that Winfrey is ready to be a public influence.

One clue to her general approach could come from the 2010 “Waiting for Superman” special, when Winfrey also underscored that education is a communal challenge, not an individual one.

“Just because your kids are in a good school, because your kids are graduated from school, doesn’t mean that it is not our country’s problem,” Winfrey said. “Our country will suffer if we continue to look the other way.”

End of an era

After leading the Memphis district through a turbulent time, Hopson thinks student achievement will ‘accelerate’

PHOTO: Laura Faith Kebede/Chalkbeat
Dorsey Hopson is leaving Shelby County Schools after nearly six years at the helm.

Attorney Dorsey Hopson took over Tennessee’s largest school district when it was in turmoil — what he described as “a mess.”

Not many would argue with his perspective. Shelby County Schools was in the midst of the nation’s largest merger of city and suburban school districts when Hopson started full-time work as superintendent in 2013. Students were leaving the district. The divide between affluent families and poor ones was growing.

But by the end of his tenure, the state department of education held up Memphis as a model of school turnaround efforts, particularly the district’s Innovation Zone. Test scores in every subject are up, even though Hopson knows they still have a long way to go.

“But now, and I think with the right attention, and the right special attention, you can see student achievement accelerate at a much more rapid pace,” he told Chalkbeat.


Related: City leaders say Hopson was the ‘right leader for a fragile time’


Now, almost six years later, Hopson is headed to a new challenge at health care giant Cigna. We sat down with him during his final days in the district’s top job to discuss his work and hope for the future.

(This interview has been lightly edited for brevity and clarity.)

You often talk about the poverty experienced by students and families in Shelby County. Do you think the rest of the state gets this?

No, because I think it’s one thing to hear about poverty. It’s another thing to see it. I think about when I got back to Memphis, we had a case and we had to go up to North Memphis. Kimberly (executive assistant) had given me, back then, a MapQuest to a house and I pull up. And I pull up and I’m thinking, like the house is boarded up and the stairs are falling down, maybe it’s the wrong house. I’m getting ready to call Kim and they say come on in. So, I go inside and it was literally like seven or eight mattresses on the floor, a bunch of fans going. You could see roaches walking around and all over the place. This is where our kids live! This is just me the lawyer who had been back four or five months. So, that just hit me like a ton of bricks.

As you go forward, when I took this role and was looking at some of the data that 40,000 kids live in households with less than $10,000, it dawned on me that’s what that looks like. I think when people think about poverty — there’s poverty, and then there’s Memphis poverty. We are one of the poorest districts and communities in the country. That is suffocating poverty.

If you’re a legislator in East Tennessee and you see a stat around poverty, it’s easy to start talking about bootstraps and all these different kind of things when your vision or thinking around poverty is not seven mattresses on the floor and a bunch of fans. I don’t think it resonates. The reality of it doesn’t smack people in the face like it should or like it does if you’re here. It presents very big challenges for everybody if you have that many kids. It’s not insurmountable, but it’s tough.

How did you take a district operating in the red to investing millions in the classroom?

PHOTO: Kayleigh Skinner
Shelby County Schools superintendent Dorsey Hopson in 2015 discusses the district’s school funding lawsuit against the state of Tennessee as former board members Chris Caldwell and Teresa Jones offer their support.

A lot of stuff. An example is obviously school closures. I think also most importantly is really pushing people around their budgets. People say I’ve got all these different heads and they say here’s my budget and here’s what I can cut. When Lin [Johnson, chief of finance] got here, we would sit down for hours, upon hours, upon hours with people going through all their budgets. It’s a lot when [a district chief] has a $200 million budget. We said we’re going to spend the next three days in my conference room — me and Lin and this person — and you got to explain to me why this is. A lot of the chiefs didn’t really understand what was in their budget. So, when you really go line by line and challenge and push, and prod, and then encourage people, and suggest to people alternative ways to do things, that makes a difference.

I think about our transportation for example. We had these routes that we had been running forever. We cut $9 million out of transportation and it wasn’t a lot of pushback and there wasn’t a lot of issues with it either.

My leadership style was such that you got to inspect what you expect. I think the legal training helped me to be very inquisitive in areas even if I didn’t really know and some people may just take for granted. And not to say people were giving you fluff or not being honest. I just think people have to be pushed to think different.

I think about when we were first starting this, we were just cutting because of the merger. If we had time to be more thoughtful like we learned to do over time, we probably could have caused a whole lot less pain.

We’ve got to talk about grade tampering. When that emerged in 2016, in the end only two people were fired and the investigation was closed because of lack of documentation. Are you satisfied with its outcome, and why should stakeholders have confidence in the integrity of the district’s grading practices now?

I can talk about what we’ve done afterward. I think that it depends on what you mean with ‘satisfied with the outcome.’ I’m still disappointed and mad that any educators would engage in stuff like that because ultimately, it cheats kids. For many of our parents and our families, the school district is that institution that represents hope. And so when you have anybody who undermines that, particularly for selfish and stupid reasons, illegal reasons and unethical reasons, I’m still deeply offended and upset that happened.

"For many of our parents and our families, the school district is that institution that represents hope. And so when you have anybody who undermines that ... I’m still deeply offended and upset that happened."Dorsey Hopson

But also having said that, when you find out something happens, all you can really do is try to figure out what happened and then, most importantly, I think in these situations put processes in place to make sure that it doesn’t happen again. Or if it does happen, you can quickly detect it. And then finally, when you find out there were wrongdoers, I think you have to take appropriate action.

The people from the auditing firm said we can keep digging and we can take your money, but it’s not likely that we’re going to find anything. So, our recommendation is to lay out these recommendations that we’ve given you to make sure this stuff doesn’t happen anymore. And we followed all those recommendations.

So, why did you not want Shelby County Schools staff to continue digging deeper on that if you didn’t want to pay the outside firm to do it?

It’s the same processes. The issue was: changing a grade isn’t, on its face, anything wrong with that. It’s just that is it a legitimate reason for a grade change? And the best way to determine whether there was a legitimate reason was the documentation. So, if you go back five years for these schools and you can’t validate the documentation, then you’re not going to ever know.

If they couldn’t do it and they’re the experts, I wouldn’t expect our people to know how to do it.

Plus, one of the things that I was comfortable with was the objectivity that happened with the whole grading thing. We didn’t do it. We had outside people do it. We had a former U.S. attorney do it. We had a forensic accounting firm do it. So, I think that if we start taking those files and taking it to our people, I don’t think that we’d be objective if we did that.

Your facilities plan presented last month was a pretty big mic drop moment. Why now?

PHOTO: Shelby County Schools
Superintendent Dorsey Hopson with students at A.B. Hill Elementary School in Memphis celebrating academic progress.

I wanted to make sure that it was something that I could at least produce before I left because I had been working on it with the team for so long. I didn’t think it was fair to ask (interim superintendent) Dr. Ray or anybody else to lead that.

At the end of the day, whatever the combination of schools are, whatever the right places to build are, you got to do something. You cannot continue to carry on these underutilized facilities that are in bad shape. Not if you expect to be able to continue the momentum.

But that’s going to require resources. You can do that when you have a plan that would help you have more money for your operating budget, reduce your deferred maintenance and then put kids in new schools. So, that seemed to me, it will go a long way, probably at least for the next 15 or 20 years in terms of stability or sustainability.

Over your time as superintendent, you closed nearly 20 schools. Do you think it’s led to better academic outcomes for kids?

I think in some instances. You get better over time, right? I think that certainly we think about Westhaven. That was the model that we’re trying to go for now. At first, keep in mind, there was the transition planning commission [during the historic merger of city and county school systems] that says you need to close 50 schools. And they made the case to close the schools to save money to close the budget gap. So, I think that initially Dorsey Hopson, a lawyer-turned-superintendent had been doing this for three or four months and has this plan that says let’s go close schools. And then you get so much backlash because it’s so much more than about the money — it’s the community hub many schools are, it’s the blight that happens if you don’t properly dispose of the building. So, you get to realize it’s not even worth it if it’s just about money.

But on the flip side, if it’s going to be about student achievement, then it does become worth it.


Related: What happens to student achievement when Memphis schools close? District report offers some answers.


So, I think about when we closed schools like Northside and Carver that literally had right around 200 kids. So, you just could not offer academic coursework, Advanced Placement classes and stuff like that at a high level when you have so few kids. And plus, you have so much extra dollars just to supplement so they can have a whole slate of teachers. So, I think the focus there was we are closing schools and take these kids to a school that is bigger with more kids where we can do more offerings.

"(Closing schools is) so much more than about the money — it’s the community hub many schools are, it’s the blight that happens if you don’t properly dispose of the building"Dorsey Hopson

But I don’t think that was the right approach either because there’s so much under the hood before you get to improving achievement.

And then the next round, we said let’s truly if we’re going to do these combinations, let’s truly invest in the school. And I think the best example is Westhaven. We’re going to invest in human capital there, we’re going to invest in additional operational dollars and give the leader more flexibility. I think that’s been great. (The state has recognized the school as having some of the highest academic growth both years it has been open.)

Let’s talk about Destination 2025, the district’s ambitious plan to improve education by 2025. Out of 39 academic goals, nine were met in the most recent annual report. What happened?

I think the new state standards were a wake-up call. Our graduation rate has increased since I took the job, but the college readiness has not. So, when you are testing college-ready standards starting in ninth grade that’s hard when kindergarten through eighth grade you weren’t being prepared for those standards and all of a sudden you show up. And not to mention, even under the old standards, people were falling behind.

Even though we did our K-8 standards-based curriculum, we still don’t have a standards-based curriculum for high school. I suspect we’ll make a recommendation around that this year.

That’s just going to be some hard work of years, rolling up the sleeves and getting better and better and better.

How would you describe your legacy?

I think that’s for other people to describe. I would hope to be remembered as a servant leader. And I think that the characteristics of a servant leader is first you got to be humble. I think this was a very humbling experience for me and I approached it from a humble standpoint because I’m a lawyer. I knew I couldn’t come in here and say I knew everything.

I think too probably more specifically around legacy, I think we’ll be remembered for fixing a lot of the operational challenges that came with the [merged] district. People forget: when we merged, it was a mess. Literally a mess.

I think that started with being able to fix the finances. We started in the red every time. There’s no wiggle room. So, I think just being able to put together consistent plans to address that stuff — part of which required buy-in from the community and getting more dollars from the county commission — but then also doing the work to get the money in order. I would hope that’s part my legacy.

Any political aspirations in your future?

No. I have people all the time saying I was running for Congress, I was running for mayor, I was going to be the next education commissioner.

When I think about all the different public roles here in Memphis, I don’t think there’s any more high-impact public position that you could have than superintendent. What you’re doing, it affects so many folks. I just know the fishbowl and the constant public grind and the board meetings and the politics and all that. I can safely sit here and say I have no desire to ever be involved in a public role.

It will be so good to be able to send an email and not have somebody ask for it. It will be good not to eat, breathe and sleep something that becomes a part of who you are. You don’t get to be off as superintendent. I can’t be in the grocery store and say sorry I’m off. You’re superintendent regardless. So, just to have some sense of normalcy will be awesome.

New leader

Lee picks Texas academic chief Penny Schwinn as Tennessee’s next education commissioner

Penny Schwinn will be Tennessee's education commissioner under Bill Lee's administration. Lee announced her hiring on Thursday, two days before his inauguration as governor. (Photo courtesy of Bill Lee Transition Team)

Fast facts about Schwinn

  • Age: 36
  • Hometown: Sacramento, California
  • Bachelor of Arts, University of California-Berkeley, 2004
  • Master of Arts in Teaching, Johns Hopkins University, 2006
  • Ph.D. in Education Policy, Claremont Graduate University, 2016

An educator who began her career with Teach For America and has been the academic chief for Texas will be Tennessee’s next education commissioner.

Penny Schwinn was tapped Thursday by Gov.-elect Bill Lee to join his administration in one of his most important and closely watched cabinet picks.

She will leave her job as chief deputy commissioner of academics for the Texas Education Agency, where she has been responsible since 2016 for school programs, standards, special education, and research and analysis, among other things.

Lee praised Schwinn’s experience as both a teacher and administrator, and his announcement touted her work in Texas to repair the state’s testing program and expand ways to get students ready for college and career.

“Penny leads with students at the forefront,” Lee said, “and I believe her experience is exactly what we need to continue improving on the gains we have made in the past few years.”

Schwinn is one of Lee’s last cabinet hires before he’s sworn in on Saturday, and she will be one of his highest-profile commissioners. The governor-elect pledged to improve public education in a state that has seen gains on national tests in recent years, even as it has struggled to transition to online exams with its own testing program.

Schwinn is viewed as a student-focused reformer but also has been criticized for the changes that she shepherded in multiple states.

“Whenever you’re talking about school improvement, that is a very difficult conversation because we’re talking about our kids and we’re often talking about change,” she told Chalkbeat. “At the end of the day, our work is about the students and what we do for them.”

Before taking her job in Texas, she was an assistant education secretary in Delaware, and previously served as an assistant superintendent in Sacramento, California, where she grew up and was an elected school board member.

She started her education career in 2004 with Teach For America, one of the nation’s largest alternative teacher training programs, and taught high school history and economics for Baltimore public schools. Returning to her hometown, she founded Capitol Collegiate Academy, a K-8 charter school serving low-income students similar to those that her mother taught for four decades.

Last year, she was the youngest of three finalists to be considered for Massachusetts’ education commissioner, a job that went to Jeffrey Riley, a native of the state.

In Tennessee, Schwinn will execute Lee’s vision on policies affecting about a million public school students, a third of whom come from low-income families.

She said that she and Lee are committed to providing all Tennessee children with access to a high-quality education and share values of transparency and honesty in reporting how students are progressing — all priorities of the previous Republican administration under Gov. Bill Haslam.

“Tennessee is a bellwether state in our country right now. The growth and improvement that we’ve seen here is impressive, and it needs to be built on,” Schwinn said.

With his choice, Lee has gone outside of Tennessee and traditional classroom training, so she will have to work steadily to build trust with the state’s numerous stakeholders in public education. Groups that represent superintendents and teachers had urged the Republican businessman to choose homegrown talent with a deep knowledge of education policy in Tennessee.

Schwinn spent much of Thursday in Nashville meeting with educators and school advocates and was welcomed with optimism.

“Schwinn shares Governor-elect Bill Lee’s commitment to support teachers, reduce our testing burden, and improve the working invironment, including more compensation,” said JC Bowman, executive director of the Professional Educators of Tennessee, an organization representing teachers.

Several leaders noted that her work to troubleshoot test administration problems in Texas should be an asset as Tennessee works to resolve its own online challenges with TNReady, now in its fourth year.

“Assessment delivery must become first in class, and Dr. Schwinn has experience administering assessment programs in two states,” said David Mansouri, president and CEO of the State Collaborative on Reforming Education.

In her first Tennessee interview, Schwinn said that TNReady will be her first priority as spring testing approaches on April 15. “Our job is to think about how to get online testing as close to perfect as possible for our students and educators, and that is going to be a major focus,” she said.

PHOTO: TN.gov
As outgoing Gov. Bill Haslam looks on, Gov.-elect Bill Lee speaks at the state Capitol the day after being elected the 50th governor of Tennessee.

Schwinn follows two education commissioners under Haslam — Lipscomb University Dean Candice McQueen and Teach For America executive Kevin Huffman — who were also reform-minded leaders hired following national searches. In particular, Huffman was a frequently divisive leader who left after three years of clashing with teacher groups, superintendents, and state lawmakers over policies ranging from teacher licensing and evaluations to charter schools and academic standards.

Setting and overseeing public education policy is among the biggest responsibilities of state government, which spends $5 billion of its $37.5 billion budget on schools and is required under federal law to administer annual tests to assess student progress.

During his campaign, Lee said that education would be one of his top priorities, promising a renewed focus on career, technical and agricultural education; more competitive pay for educators; a closer look at the state’s testing program; and more education options for parents to choose from.

Schwinn’s job will be to help Lee implement that vision, according to McQueen, who calls the state’s top education job “a unique opportunity.”

“You’re also making sure that public education is being supported well around resources and human capital and that you have high expectations for all students, not just certain groups. You have to elevate equity in every single thing you do,” McQueen told Chalkbeat last month before stepping down to become CEO of a national group focused on teacher quality.

Among Schwinn’s first tasks will be overseeing the transition to one or more companies that will take over TNReady beginning next school year. McQueen ordered a new request for testing proposals after a third straight year of problems administering and scoring the state’s assessment under current vendor Questar and previous vendor Measurement Inc. Questar officials say they plan to pursue the state’s contract again.

In Texas, a 2018 state audit criticized Schwinn’s handling of two major education contracts, including a no-bid special education contract that lost the state more than $2 million.

In Tennessee, an evaluation committee that includes programmatic, assessment, and technology experts will help to decide the new testing contract, and state lawmakers on the legislature’s Government Operations Committee provide another layer of oversight.

Schwinn also will work with the governor’s office to allocate resources for education in accordance with the first state budget pounded out by Lee and the legislature. For instance, the governor-elect said frequently he wants a greater emphasis in career and technical education in schools — an idea that is popular with legislators. But legislators also want money to hire more law enforcement officers to police schools. And despite increased allocations for teacher pay, salaries for the state’s educators continue to trail the national average.

Editor’s note: This story has been updated with new information.