The “W” flag, John McDonough and… Jeff Greenberg?  Could the current Assistant General Manager for the Chicago Cubs be the latest to jump from the Friendly Confines to the Madhouse on Madison?

Greenberg is reportedly one of three remaining finalists for the Blackhawks open GM slot. The other two are current interim GM Kyle Davidson and Tampa Bay Lightning Director of Hockey Operations Mathieu Darche.

But Greenberg is undoubtedly the most intriguing. The only hockey included on his resume is his playing days for the club team at the University of Pennsylvania. Since graduating there and Columbia Law School, he’s interned for the Pittsburgh Pirates, Arizona Diamondbacks and in MLB’s Labor Relations Department.

It’s not that uncommon seeing the NHL borrow from Major League Baseball, though.  Just look at Jon Morosi.  And he’s not the only thing each league’s network has in common.  Both channels spend much time focusing on statistically driven content.  Sports are becoming more number-based every day, whether an older generation likes it or not.  So if Jeff Greenberg has experience handling budgeting, arbitration, roster construction and trade discussions in one sport, why shouldn’t we believe he could lean on hockey people and use the analytical side of player evaluation for making up what he lacks in the other?  A source who worked with Greenberg thinks all of that is possible.

“He has that type of bandwidth and intelligence to quickly grasp those things, with this innovative mind to improve them.  I know he has contacts in the NHL from the analytics side of things that could help bridge some gaps for him if he earned this role.”

From a personality side of things, Greenberg received a glowing response.

“Many times, he is the smartest one in the room, but he has a very blue-collar work ethic to him. He wants to earn people’s respect from the quality of his work. To me, he has a combination of humility, work ethic and insane intelligence. He’s incredibly passionate about hockey.”

As soon as Greenberg was publicly listed as a candidate, the connections were easy to draw.  In December, Frank Seravalli of Daily Faceoff reported that the Blackhawks front office met with Cubs’ President of Baseball Operations Jed Hoyer to discuss the GM search.  The Cubs’ Chief Commercial Officer, Colin Faulkner, is the husband of the Blackhawks’ President of Business Operations Jaime Faulkner.  Also, John McDonough is an example of a front office executive making the leap.  McDonough left the Cubs in 2007 to be the President & CEO of the Blackhawks, orchestrated by Rocky Wirtz.

CEO Danny Wirtz, Jaime Faulkner, Marian Hossa, Eddie Olczyk, Patrick Sharp, Mike Forde and his group from Sportsology will all be involved in deciding the new general manager for the Blackhawks. The NHL Trade Deadline is March 21st.