While the Chicago Cubs and San Diego Padres aren’t playing a particularly important game today, there are meaningful games being played on this, the last game day of the season.

Of particular import, the Boston Red Sox and Tampa Bay Rays are tied for the AL Wild Card lead, with each playing its final game today, against the Orioles and Yankees, respectively. The games are important not only to the fans and players of those teams (I mean, like, who cares about them?), but also to a certain pair of executives.

And that’s where the Cubs’ hook comes in.

Two of the Chicago Cubs’ primary targets to take over as the organization’s next general manager – indeed, probably two top targets – are the men in charge of those very teams: Red Sox’s GM Theo Epstein and Rays’ GM Andrew Friedman. And, as any good self-interested Cubs fan, you’re probably asking yourself, “How exactly should I be rooting today?” We know that one team is assured a playoff spot, and one team is assured a goodie bag, so how should we best game our own hearts?



Until recently, it seemed like the preference would be Epstein’s Red Sox completing a collosal collapse and Friedman’s Rays sneaking into the playoffs. With the worst September failure in baseball history on his watch, Epstein would be a public goat, and perhaps made even more available to the Cubs. Friedman, by contrast, seemed no more or less likely to pursue other opportunities, regardless of his team’s performance. So, if the Rays rallied to make the playoffs, the Cubs would be no worse for the wear.

That conventional wisdom, however, could be wrong, says Ken Rosenthal.

It’s almost impossible to imagine him leaving his hometown team in a moment of epic failure — if indeed the season ends in such fashion.

“He would never be allowed back in the city of Boston,” one rival GM said Tuesday.

Then again, this could go the other way, too.

The Red Sox, if they miss the postseason for the second straight year, could make a series of impulsive moves. One such move might be allowing Epstein to leave with a year left on his contract ….



Boston is an emotional market. Someone — maybe a few someones — would be held culpable if the Red Sox blow it. But the Sox under Epstein and owner John Henry have taken great pride in removing emotion from their decisions.

Henry is fond of Epstein and will not want him to leave. Epstein has never said he was interested in the Cubs and never said he wasn’t. But the way this is unfolding, the timing just isn’t right.

In fact, one member of the organization said he would be “shocked” if Epstein left, saying that the GM is deeply invested in the Red Sox and excited about the team’s future.



Unfortunately, this makes sense. Epstein was always an uber long-shot, and we knew that it would take something extreme to shake up his strong tie to Boston. A shocking collapse sounded like it would fit the bill, but, upon reflection, would a local guy – a favorite son of the city – really leave his organization on the heels of the worst performance in team history? He’d be called a deserter. A turncoat. A traitor. The Cubs, if they ever really had a chance at Epstein, seem to be the victim of circumstance.

Unless, that is, Epstein’s Red Sox win the Wild Card, and maybe even a playoff series or two.

What about the team his Red Sox would be excluding? What’s the story with Rays’ GM Andrew Friedman, anyway? Phil Rogers says Friedman is actually becoming more of a possibility for the Cubs.

According to MLB sources, Andrew Friedman, the brilliant architect of the Rays’ homegrown success, seems more in play in the Cubs’ ongoing search for a general manager than he did a month ago. He and manager Joe Maddon feel like they’re hitting their heads against a wall in trying to help owner Stuart Sternberg grow baseball interest in the football-crazed Tampa Bay area.

Would Friedman be willing to talk to Chairman Tom Ricketts about running the Cubs? Most thought that highly unlikely given his ties to Sternberg but would anyone blame Friedman for wanting to see what it is like to have big-market resources?

The answer to those not-quite-rhetorical questions, we hope, is yes.

So, now, if you’re looking for a rooting position today, it seems best to pull for the Red Sox. If Epstein won’t leave under a cloud of failure, maybe he’ll leave until the sunlight of renewed success. And, if the Rays miss the playoffs once again thanks to the big boys of the AL East, maybe Friedman will be just a little more likely to look around.


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