For those who are unfamiliar with Roosevelt and Pittsburgh, here's a little bit of background info: Roosevelt came to Pittsburgh a little over 5 years ago with no experience as a teacher, principal, or district administrator. Which isn't to say was completely unqualified or without talent or relevant experience. He had a law degree from Harvard, worked on education issues as a state legislator in Massachusetts (where he later ran for Governor), and served as a CEO and in various other leadership positions. He then completed a fellowship with the Broad Foundation (not sure of the exact name of the program, but it was a 10 month program that dealt with leadership in urban schools) right before his appointment.
When he came to Pittsburgh, the district was most famous for its contentious (and that's being kind) board of ed meetings -- so contentious that a large number of foundations had pulled money from the district and warned that they'd better straighten up if they wanted to get it back. At the same time, the city of Pittsburgh has fewer than half the residents that it did 60 years ago. 100 years ago it was the 8th largest city in the country and, I believe, had more corporate headquarters than any American city outside NYC (that might not be exactly correct, but the point is that it was a major center of industry).
Which means two things for the city and district: 1.) that they had far fewer students, but not far fewer schools, and 2.) that there's a lot of foundation money, per capita, in the city. Which meant two things for Roosevelt: 1.) He needed to shrink or close schools, and 2.) he needed to make the foundations happy.
He closed 22 schools in all, and reconfigured many more. Whether or not this was the correct move, one must admit that it took political courage and saved the district money -- and that it also upset a lot of parents living near schools that were closed or changed. He's also been a big hit with the foundations. The major Pittsburgh newspaper, the Post-Gazette, ran two stories on Roosevelt today (here and here), both of which are full of praise from all sorts of people.
Which is why it surprised me that he was leaving. Yes, some parents and teachers didn't like him. But the foundations loved him, the board of ed loved him, the mayor loved him, and the union barely put up a fight (they recently agreed on a 5-year contract). I really have no insight into why he left -- I don't know the man personally and am unfamiliar with the day-to-day operations of his office -- so my best guess, given his previous frequent career-hopping, is that he was telling the truth when he said that he simply needed a new challenge.
The gist of what I've read and heard about him over the years is that he has many of the same strengths and weaknesses of a typical businessman. He obviously got along well with the foundation people and the board of ed (a definite plus compared to previous regimes), but nobody would confuse him for a community organizer or former teacher. The result was an administration that seemed to run smoothly and attracted lots of outside dollars, but didn't spend much time asking parents or teachers for advice.
Saying he ran the schools like a business would be cliche and overly simplistic, but he clearly wanted to streamline things. He closed schools, narrowed curricula, and hired principals who would do things his way.
From the second article in the Post-Gazette: "In the classroom, Mr. Roosevelt sought to make teaching more consistent, including instituting a managed curriculum that required teachers to use certain materials and to present them at a certain pace. The recent teacher survey showed that some teachers think they have too little role in decision-making."
In the lower grades, the district closed many of the lowest-performing schools and moved the former students to K-8 "Accelerated Learning Academies" with extended hours and years. In the upper grades, the vo-tech high school, and many other vo-tech programs, were closed in the name of academic rigor, scripted curricula were implemented, and he began opening small, specialized schools. He leaned heavily on paid outside help to accomplish these reforms. RAND evaluated all the schools, America's Choice provided the procedures and curricula for the ALA schools to follow, Kaplan wrote new HS curricula (and then was asked to leave so the district could re-write them themselves with some help from Pitt), and an outside firm was hired to run an alternative school for students with consistent discipline or attendance problems. In the long run, he might be best remembered for starting the "Pittsburgh Promise," a fund that aims to pay full college tuition for qualifying district students who attend PA state colleges. The fund got off to a rocky start, but is now much closer to its $250 million goal thanks, in part, to Roosevelt's relationship with local foundations.
In the end, he upset a number of parents and teachers. Though the union rarely criticized him, there was a sharp divide between the attitudes of elementary and secondary teachers -- with the new contract being passed due to overwhelming support from the former and despite heavy opposition from the latter. The lack of opposition from the union led to the election of some non-slate candidates in the last election who'd promised to be less docile.
And I'll be the last to argue that at least some of this anger was warranted. I've written in the past that his new grading policy was poorly implemented and his newer system, though a little better, didn't work the way it was supposed to, that teacher morale was suffering under his leadership, and that some of his rhetoric was unhelpful. But I'll be the first to admit that Pittsburgh could do a heck of a lot worse than 5+ years of more or less smooth sailing with the foundations, the board, and the union to go along with a steady stream of new ideas (some good and some bad).
But love him or hate him, one has to admit that it's somewhat irresponsible of him to step down abruptly in the middle of such turbulent change (and, personally, I think leaving mid-year reflects poorly on him -- but you're entitled to your own opinion). This is the first year of a new $80 million dollar program (funded by Gates and the federal govt.) to re-vamp teacher pay and evaluation, numerous schools and students are slated to be reconfigured and moved next year, and he has a million other balls up in the air. I think everybody can agree that he's done some good things and some bad things (though they certainly won't agree which things were bad and which were good), but I think everybody can also agree that he didn't finish the job. It may or may not prove to be a good thing for the city/district that he didn't finish the job, and there may or may not be some very good reason(s) underlying the decision, but I'm somewhat disappointed in him personally for being willing to pick up and leave before the job is done.
Why? In the midst of the effusive praise lavished on him by people of all different stripes was this quote from a leader of a local parents group: "Our group would ask that all initiatives be placed on hold until a new superintendent is found . . . We don't want all this money, expense, experimentation done if a new superintendent is going to take it in a different direction." I don't know how many months it's going to take to find a new superintendent or how many of the current reforms will continue under his/her leadership, but the changeover seems pretty likely to result in a lot of uncertainty, hesitation, and delays. Which can't be what Roosevelt thinks is best for the district.