Nah, Barbara Gray was one of the better ones, particularly pro-pedestrian and cyclist compared to predecessors. We can of course keep doing better (and there are a lot of dinosaurs both on council and in the civic service), but we did get some major bike and pedestrian improvements in the last decade, at least until Doug Ford decided that his buddies and donors were more important.
I think I will split the difference between your take, and
@Amare 's
Barbara was a decent person, if you met/dealt w/her. She was indeed pro cycling and broadly supportive of that unit, to her credit.
In fairness to her, she also faced budgetary challenges; and the Gardiner project soaked up a large chunk of the department's budget for years.
That said, there is a lot of dead weight in that department and many services did degrade over the years for a slew of reasons from budget to contract oversight etc.
She could have been better at ousting some folks and demanding more of others and providing the requisite training/supervision to get that extra out of them.
While I appreciate that Councillor's are a material part of the problem, she's been unable to check the 'a traffic light for everyone' crowd, which has eaten up millions that could have delivered other needed projects.
For reasons that go beyond Barbara, the City has been unwilling to bar certain under performing contractors from bidding on projects, and procurement........seems to give same a free pass.......but I digress.
There is also a tendency to take far too long to deliver projects, I don't even mean the construction schedule (though that too), but rather designs being done so early relative to construction they have to be re-done as so much has changed by the time the project is queued up. Again, there's a lot going on there and she certainly doesn't wear all of it, maybe even most.
But 'the buck stops somewhere' and that is her chair.
*****
Whether her retirement is good or bad will depend entirely on who her replacement ends up being and any resulting staff shuffle.
When Barbara came in, several senior staff exited. That's normal by the way, when new top people come in, particularly from the outside, they often to try to bring someone with them, and to reshape their department leadership to their liking.
There are several people in that department worthy of elevation; and more than a few whose best before date is long passed.