Is RemDawg's Empire Expanding or Collapsing?

The RemDawg is set to deliver The State of Red Sox Nation at his new restaurant: Jerry Remy’s Sports Bar & Grill in Terminal C of Logan Airport on Friday April 17 at noon. Remy will then take questions from fans and judge a singing contest of Take Me Out to the Ballgame with Wally.

You would think with an event like the one above that things are looking good for the RemDawg empire but if he keeps losing bets in the broadcast booth he may be in for a hard fall.