Cubs-Indians World Series Shaped By Some Of Red Sox’s Most Pivotal Decisions

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The 2016 World Series will feature two well-respected baseball men, both on the verge of cementing their statuses as Hall of Famers.

In the Cleveland Indians’ dugout Tuesday night, manager Terry Francona puts his unblemished World Series record on the line against the Chicago Cubs. Somewhere at Progressive Field, Cubs president of baseball operations Theo Epstein will sit and watch the team he built try to bring a world title to the North Side of Chicago for the first time in more than 100 years. It’s likely a win would secure a place in Cooperstown for either man. 

For Boston, it’s impossible to see this matchup and not think about the most successful era in Red Sox history. Francona and Epstein worked alongside each other in Boston, teaming to erase a near-century title drought. The duo led the Red Sox to their first championship in 86 years by winning it all in 2004. They then won it again in 2007, ending a much shorter drought.

There’s a natural tendency to look at the Cubs and Indians — starting with and focusing on Francona and Epstein — and see that a handful of decisions made by the Red Sox actually set the stage for the 2016 World Series.

It’s impossible to think Epstein and Francona would stay in Boston together forever. Epstein said as much in a public goodbye to Boston and at his introductory press conference in Chicago, citing Bill Walsh’s theory that change is important to sustaining organizational success. On- and off-the-record reports from the Epstein/Francona years seemed to indicate change probably was needed.

Lamenting what could have been for Red Sox fans doesn’t do much good. Epstein and Francona delivered a pair of world titles — Epstein setting the table for a third in 2013, too — and it’s hard to complain about those results.

And the fact Epstein and Francona didn’t reconvene in Chicago, in a way, reinforces the notion it was important for them to cut ties after the Red Sox’s disastrous 2011 season.

In some ways, that horrendous 2011 collapse helped set the wheels in motion for this World Series matchup in 2016. The Red Sox held a two-game division lead as late as Aug. 27, yet they finished seven games out in the American League East. The wild card still was in play until the final game of the season, but that also infamously went up in flames.

Changes obviously would follow one of the worst collapses in baseball history. It didn’t take long for the Red Sox and Francona to “part ways,” but a damning story in The Boston Globe hinted that Francona had lost the clubhouse, making one wonder how mutual the parting really was. Epstein exited days later, heading to Chicago in the hopes of rebuilding another storied franchise soaked in misery.

Just like that, the Boston baseball machine responsible for two world titles was in disarray. And despite an out-of-nowhere title in 2013 and a promising division title in 2016, the Red Sox haven’t been the same since, cycling through two managers, a general manager and a president of baseball operations.

Epstein did exactly what he promised he’d do in Chicago. He built another baseball operations machine rooted in relentless scouting and player development and shrewd wheeling and dealing — all while keeping his promise to instill a “Cubs way” throughout the organization.

Francona eventually landed on his feet in Cleveland, where he’ll now look to become the 11th manager in baseball history with at least three World Series titles and just the third to do so with two different organizations.

At a certain point, though, it’s inevitable for that sort of change. And the toughest pill for Red Sox fans to swallow while watching the World Series might not even have anything to do with Francona or Epstein.

Taking the mound Tuesday night for the Cubs is another name from Boston’s baseball past, Jon Lester. The left-hander still is widely considered one of the best pitchers in baseball, and he only gets better when the lights shine brightest.

Lester has an impressive 2.50 career postseason ERA and has been even better since joining the Cubs. He has a 2.31 ERA in his four postseason starts with Chicago, taking his game to another level in 2016 by allowing just two earned runs over 21 innings so far and earning co-MVP honors in the National League Championship Series.

The worst thing about losing Lester, from a Red Sox standpoint, is he said all along he wanted to remain in Boston. According to reports, Boston came in low with its first offer. It’s impossible to know whether that soured Lester to the negotiation process from the beginning, but he’s not wearing that “B” on his cap anymore, and that’s all that matters. Perhaps the Red Sox also were afraid of giving Lester, who turned 30 before reaching free agency, a mega deal as he prepared to seemingly enter the twilight of his career.

Of course, two years after trading Lester and failing to re-sign him when he hit free agency months later, the Red Sox gave 30-year-old David Price — and his now 5.54 career postseason ERA — a seven-year contract worth a reported $217 million.

Those aren’t the only ex-Red Sox playing over the next week, though. The World Series is littered with players, coaches and executives who used to call Boston home.

Mike Napoli, after scuffling his way through the 2014 season, is enjoying a renaissance in Cleveland.

Anthony Rizzo, who the Red Sox traded for Adrian Gonzalez (who was flipped late in 2012 in a salary dump), now is a perennial MVP candidate in Chicago.

John Lackey, who suffered through the chicken and beer saga before helping Boston to the 2013 title, will start Game 4 for the Cubs.

Andrew Miller, traded by the last-place Red Sox in a 2014 firesale before signing with the New York Yankees in the offseason, now is arguably Cleveland’s most important player.

And we could go on.

The Red Sox, with Epstein and Francona (and everyone else), had their time and found great success. But with all the Boston connections in this World Series, it’s natural to play the “What if?” game.

We’ll never know exactly how much success Epstein and Francona would continue to have in Boston had they both stayed, but this World Series — where one again will emerge as a world champion — gives us a pretty good idea of what could have been.

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