Theo's ‘biggest regret' not Cubs' biggest problem last 3 years

Theo Epstein’s legacy in baseball and in Chicago has been secure since the end of that 10th inning in Cleveland four years ago this month.

The architect of the teams that broke the two most famous baseball curses — of the Bambino in Boston and the billy goat in Chicago — 12 years apart is assured a place in Cooperstown for a career as an executive that has yet to take him to his 47th birthday.

He recalled some of those successes and handed out a long list of thank-you’s during a Zoom session with reporters on the day he announced his resignation — a year early — as Cubs president.

He also recalled his greatest regret since the World Series when asked — but left out the biggest problem.

“It’s sort of obvious. Our postseason performance since ’17,” said Epstein, who famously said after the 2018 season that the team’s lineup, built around a homegrown core, “broke” in the second half that year.

“Our performance when it really mattered I thought was our calling card for us through ’15, ’16 and even into ’17 if you look at the Division Series [against Washington] that year,” he said. “And I felt that was a part of our identity and something we could rely on, just that when our backs were against the wall we tended to find a way to play our best baseball.

“And for whatever reason we just have not done the same in big moments in the last three years,” he said. “That’s a regret.”

What Epstein left out was the biggest failing of his administration in Chicago — which likely had an impact on those results.

The inability for the last nine years to develop homegrown pitching, especially starting pitching. Despite making the playoffs in five of the last six years, the Cubs haven’t had a homegrown pitcher throw playoff pitch since 2008. Until this year, left-hander Rob Zastryzny was the only homegrown pitcher to make a postseason roster and only for the 2016 NLCS against the Dodgers.

That’s the biggest reason the Cubs had $77.5 million in starting pitchers on this year’s roster (before salaries were prorated for the short season) and why they spent $138 million on a 2019 pitching staff in a year they missed the playoffs.

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A third or fourth starter and a couple of back-end bullpen guys from the farm system in the last three years alone would have lowered the payroll pressure at a time the hitting core started making arbitration salaries that chewed quickly through the budgets.

How different might those last three years have looked with a low-salaried homegrown starter ready by 2017? Would they have been as compelled to trade for Jose Quintana? Would they have rolled the dice on the higher-risk, higher-reward Justin Verlander (who wanted to go to the Cubs instead of the Astros that year)?

How would the Tyler Chatwood-Yu Darvish-Brandon Morrow winter played out? Or the subsequent need to trade for Cole Hamels — then pick up his $20 million option for 2019?

A lot of what-ifs, no doubt.

But it was hard not to connect those dots when Epstein talked about that big regret Tuesday.

“Obviously, we’ve invested a lot of resources, both in terms of just payroll, but probably more importantly supplementing [the core] through trades to put this group in position to have those big moments and to come through,” he said. “And I didn’t do a good enough job or else we would have come through in those situations.

“I just wish that we would have found a way to play better baseball in the big moments the last three years,” he added, citing the 95-win success in 2018 that often gets lost in the low-scoring losses that quickly ended their season in Game 162, the subsequent Game 163 division tiebreaker and then the wild-card game.

“And then in ’19 we were so well positioned going into September with a lot going for us, and this past year we won the division,” he said. “But in all three instances we had nothing to show for it that counts, long term, in terms of the flags that fly forever.

“That’s probably my biggest regret as I look back.”