Why Did Caleb Pressley Leave Barstool Sports? Barstool Sports continues to bleed talent as Dave Portnoy cries poor claiming he doesn’t have the resources to keep them. The Bussin with the Boys crew is leaving Barstool. So is Caleb Pressley, who just might be the quickest-minded funny person that company has. Well, did have because … Continue reading Why Did Caleb Pressley Leave Barstool Sports?