Newspaper sportswriting and the Chicago sports scene will have to weather the loss of columnist and reporter Teddy Greenstein. After 24 years at the Chicago Tribune, Greenstein announced Friday morning that he was taking an editor position at PointsBet Sportsbook.

Fans of the Big Ten and Notre Dame might miss Greenstein’s coverage the most. The Northwestern grad reported on his alma mater for the hometown newspaper. (Michigan fans loved pointing out where Greenstein went to school.) But he’s one of the leading voices on college football and basketball in the Midwest (and for a national readership as well).

Interestingly, most of his reporting during his final months at the Tribune concerned whether or not the Big Ten would play football this season. Now, just as the Big Ten is set to kick off a delayed 2020 campaign, Greenstein is moving on.

Many sportswriting colleagues and staffers at Big Ten programs offered congratulations after Greenstein announced his move.

His final column for the Tribune focused on Northwestern football, listing 100 facts about coach Pat Fitzgerald as he approaches 100 wins leading the Wildcats program. Among them:

  • Fitzgerald was persuaded by Gary Barnett to play at Northwestern, not Georgia Tech.
  • The Green Bay Packers pursued Fitzgerald for their head-coaching position, but his sons shot the idea down.
  • Fitzgerald also turned down interest from Michigan, which offered to triple his salary.
  • Before becoming a coach, Fitzgerald sold ad time for One On One Sports radio network (now SportsMap).

Greenstein also covered Major League Baseball, the NBA, and golf in a very rich Chicago sports landscape. One of his most fun recent pieces chronicled an investigation into which two Chicago Cubs games were involved in filming the matinee Ferris Bueller attended while skipping school in 1986’s Ferris Bueller’s Day Off.

“Baseball Prospectus’ Larry Granillo figured out that the game Principal Ed Rooney watches from the counter of the pizza joint was played June 5, 1985. An 11th-inning pop-up by the Atlanta Braves’ Claudell Washington gave it away.

“But here’s the rub: The scene wasn’t filmed that day. Actor Matthew Broderick (Ferris Bueller) and Alan Ruck (Cameron Frye) did their ‘swing batta’ routine from seats down the left-field line on Sept. 24, 1985.”

With sports betting currently legal in only a few states, Greenstein’s beat will still largely stay in the Midwest. Illinois, Indiana, and New Jersey are among the three states where PointsBet does business. So he’ll still have plenty to report about the Big Ten and Notre Dame, but will likely take a more national view with his work too.

And as he said himself, Greenstein gets to indulge his knowledge and interest in sports betting with this new venture, one that will continue to grow as sports betting becomes legalized elsewhere throughout the country.

However, the Chicago Tribune sports section just won’t be the same without him. Greenstein’s departure is yet another blow for newspapers and traditional sports media.

About Ian Casselberry

Ian is a writer, editor, and podcaster. You can find his work at Awful Announcing and Asheville's Mountain XPress. He's written for Yahoo Sports, MLive, Bleacher Report, and SB Nation.