Departure Conflict at Midway; DAL SWA

[SpauldingSmails]

Why would he captain me any more or less aware of the similar call sign than the FO?

Well, honestly, because DAL procedures have the Captains extremely task saturated IMO. From the time the flaps drop and we commence taxi, until reaching the end of the runway we'll run a minimum two checklists and a couple partial heads-down verification processes. It's actually kind of nuts. Further, if a runway change takes place, or the taxi was commenced single engine, you've added even more. So, between taxiing the aircraft, responding to checklists, and then having to go "in and out", the Captain can easily miss something. I've seen it many times. Compared to procedures at my previous airline taxi out is a bit of a circus.