Round 2 opens today with another great matchup between the only local announcer to make the last 16 and ESPN’s windbag of debating debauchery.  The voice of the Yankees, John Sterling, battles with the centerpiece of ESPN’s First Take, Skip Bayless.  Like Round 1, polls will be open until the next matchups go live the next day and we’ll have two Second Round matchups going each day.  That means Round 2 will go from Thursday-Sunday with the recap and Quarterfinal draw coming Monday.  

John Sterling vs Skip Bayless


John Sterling

Fact File: New York Yankees play by play man

Why He’s Here: Sterling is one of those rare announcers that has become a caricature of himself.  His Bermanesque homerun calls can be painful even for the most ardent of Yankee fans.  They wouldn’t be so bad if Sterling didn’t routinely botch even the simplest of commentary.  His trademark “Yankees win, THHHEEEE YANKEEEEES WIIIINNN” call is the anthem of the seventh circle of hell for baseball fans outside New York.


Derek Jeter’s 5,000th hit?
John Sterling Is Utterly Confused
John Sterling Being John Sterling
The Sterling Shake

Round 1 Result: Defeated Matt Millen 58.69% – 41.31%

Skip Bayless

Fact File: “Star” of ESPN’s First Take and 1st & 10

Why He’s Here: The former antagonizing columnist transformed into an antagonizing TV personality with his transition to first Cold Pizza and then First Take on ESPN2.  Bayless traditionally squares off against a debate partner in segments that contain enough hot air to lift the Hindenburg.  Often, Bayless will say outlandish things just for the sake of saying outlandish things.  Thankfully, most people have stopped listening.


Rob Parker & Skip Bayless Said What About Chad Ochocinco
Skip Bayless And Chris Broussard Have Exchange For The Ages
Nelly: Why rappers want to kick Skip Bayless’ butt on ESPN
The Best (Worst) Of Skip Bayless – 2006 

Round 1 Result: Defeated Woody Paige 77.91% – 22.09%


Skip Bayless defeated John Sterling  64.14% – 35.86%

About Matt Yoder

Award winning sportswriter at The Comeback and Awful Announcing. The biggest cat in the whole wide world.