I actually see it being a lot like Ted and Dinah’s relationship, to be honest!
The interesting thing about Ted, and one of the reasons he’s easily one of my favorite male characters in the DCU, is that he actually has a very subtle hand with almost every major character’s development in the preboot continuity. He just has a lot of impact on all the people that are just huge and yet those relationships seem to be really unsung at the end of the day.
In Gotham, he’s had a relationship with Bruce over the years that’s just self evident, Dinah is something of a figurative daughter for him, he’s on Oracle’s call list for Birds of Prey missions, he and the rest of the JSA are on great enough terms with Dick that they help him move out of his New York base, and he’s had adventures with Tim during Tim’s Robin years.
Mostly, for me anyway, he’s greatest in the Gotham circle when we see the way his relationship developed with Selina. That’s how I really came to love Ted and respect him, and it’s really why I think having Ted work with Cassandra would be great for both of them.
Ted loves teaching students, it’s a thrilling challenge, especially when they’re much better than him. He has the fundamental idea that anyone and everyone has something to learn, even if they have superpowers or can out-fight him. He teaches people about life, something he has plenty of experience with. And Cass does have a tendency to gravitate toward strong personalities and good souls. She’d bond very easily with Ted, I think.
I… actually really want to see this happen now. Plus more to draw my “Cass & Dinah, Cass & Sin” postulations that I love.