5 challenges for Cubs with Epstein locked in

Ninety-five wins a year. That was the Red Sox’s goal in the Theo Epstein years, because they were competing against the Yankees. As staggering as that number seems, the Red Sox were actually underselling the greatness of the Yanks.

In the Derek Jeter era, the Yankees averaged 97 wins over the course of 17 seasons. That’s the same total that the Braves averaged over 14 full seasons in their great run during the Glavine-Smoltz-Maddux years.

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The Cubs have taken their first steps toward establishing themselves as a powerhouse, piling up victories with a young team, a resourceful front office and strong ownership that is growing revenues.

They won 97 games in 2015, and they enter the last four games of this season having already won 101, the most in the Major Leagues. Will we look back on the Cubs a decade down the road and see that they followed the same path as baseball’s most consistent winners?

When Tom Ricketts extended Epstein’s contract for five years on Wednesday, paying him about $10 million a year, it was a no-brainer for all parties involved. Epstein, whose title is president of baseball operations, seemed happiest about the news that general manager Jed Hoyer and vice president of player personnel Jason McLeod are also expected to get extensions that run through 2021.

The people most responsible for building the Cubs are being paid at the top of the scale in a business where executives have historically been paid like players who hit seventh or eighth in the lineup. Ricketts is changing the way front-office staff is valued, and that makes it a little bit harder for clubs to pry away those who work alongside Epstein.

Epstein’s challenge was clear when he arrived in Chicago in October 2011. He had to improve the organization in almost every way while creating what he called a “player-development machine.”

He’s done that in A-plus fashion, thanks in large part to shrewd trades that brought Anthony Rizzo, Addison Russell, Jake Arrieta, Kyle Hendricks, Dexter Fowler and Carl Edwards Jr. to Wrigley Field. But the challenges that lie ahead are crucial if Epstein is to …

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