Any idea why this shift shaft seal would be leaking?

My son's transmission has been leaking since he bought the car. And it has progressively gotten worse. Pretty much knew where the leak was coming from and what I had to do. And of course we forgot to do it while the engine and trans was out of the car. Duh. Oh well I've done them before, not that big a deal.

Got the levers off, reached up there amongst it and something didn't feel right immediately. Stuck my camera up and took these pictures. Really? Why in the hell would anybody bother to do a half *** job like this?

Question is do I press it on in and see what happens or go ahead and change it out. At least it'll be easy to get out. Think I'll just go ahead and change them. Got both seals sitting here anyway.