It is hardly a coincidence that the funniest character on Grey's Anatomy shares his first name with the funniest character on Seinfeld: George. Okay, so George O' Malley is nowhere near as selfish, chubby or balding as George Costanza, but he is every bit as insecure, as shown in all its glory in this episode.
What started like a normal day becomes a mess rather quickly: an annual bike race is causing several people to wind up at the hospital (the poor idiots think it isn't fun to ride on the sidewalks), including one man who is declared officially brain-dead in a short amount of time. At this point, Izzie and Cristina think it would be a good idea to remove his organs for donation, an idea that would certainly please Lloyd Mackie (Keith David), a cancer-struck friend of Dr. Webber who's been waiting for a new liver for eight months and kills time by flirting with the intern in charge of looking after him: George. In the meantime, Meredith keeps resisting Derek's offers to go out on a real date.
For the first time, what happens on the operating table has an effect on the young doctors and their ethics system - Izzie, in particular, starts to resemble a proper character instead of a mere caricature of juvenile idealism (then again, she used to be a model, so maybe it was deliberate), an element that will be explored further in later episodes. What really makes Winning a Battle, Losing the War memorable, though, is the interactions between George and Mackie: T.R. Knight seems to channel Jason Alexander most of the time, especially when he insists he isn't gay (a bit ironic, given the actor came out during the production of Season Three), while Keith, best known as a voice-over artist, exudes tons of charm with his relaxing, paced words, brilliantly subverting the "dirty old man" cliché.
Overall, pretty good: entertaining, occasionally moving, and clear proof of the show's fine eye for guest stars.
7,5/10