"This is John Winchester. I can't be reached. If this is an emergency, call my son, Dean at 866-907-3235. He can help."
First new message. Sent at 5:45 p.m. on December 25, 2005 from phone number 866-907-3235 "Dad, it's Dean…again. Just wanted to tell ya' merry Christmas and all that crap. Sammy and I are doing good. It'd be great if you could…I dunno…answer your phone. We're in Michigan right now so there's snow everywhere. Nailed him in the back with a snowball, it was pretty cool."
Second new message. Sent at 7:13 p.m. on December 25, 2005 from phone number 866-555-9301 "Hey, it's Sam. So…merry Christmas. Dean and I are in Michigan, just finished a hunt for a black dog. It got a good chunk out of Dean's leg but he's fine now." Sam pauses for a minute before continuing, "Wish you'd call me back. Dean, too. He won't admit it but I know he's calling you Dad. I know I'm not your favorite person in the world but don't do this to Dean, Dad. At least call him back. He deserves it."
Third new message. Sent at 8:00 p.m. on December 25, 2005 from phone number 866-555-9812 "Hey Johnny, it's Caleb. Just wanted to call and tell ya' to have a good Christmas but I guess you're not answering calls right now. I'll just call Dean, then. See ya' around."
Sorry it's been such a LONG time. I was on Supernaturalwiki and the dates from when the episodes take place skip over Christmas so…tada! I think Bobby would have called the Winchesters during Christmas. So why not throw in Caleb? But Bobby probably would have already tried calling John, so would have Jim in my opinion.