I'm tired of pretending that not having you here isn't killing me. That every time I lose someone else, it doesn't take a little part of me with them.
—Tim Drake, Robin #167
While most of Tim's most devastating losses actually occur in other books their impacts are keenly felt and they significantly steer the course of the later part of the series.
- Though it took place prior to the start of the series Tim's heartbreaking response to Bruce when he wakes up in Batman #455 deserves a mention:Bruce: Better get up. I…hate to remind you, but today is–
Tim: The funeral. Her funeral. My Mommy’s funeral. - Jack's descent into depression after he bankrupts Drake Industries is quite bleak. He ends up locking himself in his room not speaking to his wife or son while finding himself having a difficult time choosing between his living family and his dead wife.
- Tim makes up a fake uncle to avoid having Bruce adopt him due to the role Bruce's duplicity played in Stephanie's death, especially Bruce hiding from Tim that Stephanie was missing during the hours Black Mask was torturing her to death. He also notes on several occasions that he'll never be able to fully forgive or trust Bruce for hiding that Stephanie was dying and keeping him from even having the choice of trying to make it to the hospital after she was found.
- The quote above is the start of a depressing soliloquy Tim makes during a downpour at his parents' shared grave after a night where he failed to keep a little girl from witnessing her own father's murder. Bruce shows up immediately to take him home but Tim still makes promises to his parents that he will die before allowing such a thing to happen again and laments the loss of so many of his friends along with his entire biological family.
- Tim spends some time missing Steph, being dismayed that she hasn't been given a memorial in the Batcave and that she's basically a taboo subject to bring up around Bruce shortly after he decides to try going on a date with Zoanne. Steph returns and her death is retconned away as having been faked by Leslie not long after, at which point Bruce claims the reason he never gave her a memorial was because he suspected the duplicity. Tim feels betrayed by Bruce for not informing him, and a little betrayed by Steph for leaving him thinking her dead for over a year as he watched his remaining family and both of his best friends end up murdered but he's mostly just overjoyed at her return despite the betrayal of trust.
