History repeating itself isn't exactly what the Orioles should be looking for as they search for a new direction with their hires of a front office that is likely to include an experienced president of baseball operations to oversee a new staff that includes a younger, up-and-coming general manager type.
Yet as the rival Boston Red Sox celebrate a fourth World Series since 2004 after a summary dismissal of the Los Angeles Dodgers, it's not the fact that former Oriole Steve Pearce won the World Series MVP or the odd revisionism on their feelings about Manny Machado that Orioles fans should be focusing on.
It's that just as last time they conducted such a search and ended up with Dan Duquette, the man whose fingerprints were all over the Red Sox's 2004 World Series run, this search might be best executed if it leads to former Red Sox general manager Ben Cherington.
Cherington, who held a variety of roles with the Red Sox from 1999 under Duquette until 2015, serving as the general manager from November 2012 to August 2015, is currently the vice president of baseball operations for the Toronto Blue Jays. While the Orioles' search is being conducted in strict silence, there have been some overtures in the past and the Orioles' absence when it was reported that Cherington wasn't interested in the San Francisco Giants and New York Mets top jobs was noteworthy. The reasoning that he wanted to build a franchise from the ground up certainly fits, too.
Duquette proved to be a fine fit for a team with a tremendous young core that needed some augmenting around the fringes. In Cherington, who has been an amateur scout, international scouting coordinator, and director of player development in addition to his lead front office roles, the Orioles could find someone who is adept with the best practices of building up each of those departments for an organization that's targeting improvements in each.
The focus in examining Cherington's candidacy will be on his time in charge of the Red Sox after Theo Epstein's departure following Robert Andino’s ending the 2011 season for Boston. The 2012 season was a nightmare, but Cherington dumped the salaries of Adrián González, Josh Beckett, and Carl Crawford to set himself up for a reload in the offseason that led to a World Series title in 2013.
What followed were some missteps in free agency with the likes of Pablo Sandoval and Hanley Ramírez that ultimately came to define most of his time in Boston. But there were just as many deft moves (like signing Rick Porcello) as high-priced clunkers, and hiring Cherington would signal that the Orioles aren't just paying lip service to building themselves a drafting and development machine.
His fingerprints were all over the Red Sox team that won on Sunday. Sure, he didn't trade for Chris Sale, but he signed Cuban Yoán Moncada for $31.5 million (and paid a 100 percent tax because of Boston's robust international presence) and oversaw the selection of Michael Kopech in the draft, the two players his successor Dave Dombrowski sent to Chicago for Sale's services. His players were also a significant part of the trades for closer Craig Kimbrel and left-hander Drew Pomeranz, and he traded Andrew Miller to the Orioles for Game 4 starter Eduardo Rodríguez. Jalen Beeks, who was traded to Tampa Bay for Nathan Eovaldi, was also drafted under Cherington.
But the likes of Porcello, Rafael Devers, and Andrew Benintendi all came into the organization under Cherington, and his operation brought the likes of Mookie Betts, Xander Bogaerts, and Jackie Bradley Jr. to the majors.
Because he came between Theo Epstein and Dombroski, it's hard to quantify Cherington's role in what the Red Sox have done the past 15 years. What's clear is that he fits everything the Orioles are looking for, and that’s simply experience in an organization that used everything at its disposal, from scouting and player development to analytics, to build a complete team.
If they want someone with a background in all the areas they've fallen behind in, he can do that, and oversee the large staff they envision allowing said executive to build. Cherington's ideas on creating a holistic approach that involves all facets of the organization going in the same direction will be a welcome change from the fractured nature of things previously. Even if he wasn't personally responsible (and at times he was), Cherington knows what a working setup in every facet of an operation looks like.
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If the Orioles want someone who has held the proverbial big office and run all of that setting the philosophy and another executive to learn to do that and execute the day-to-day, Cherington's experience will prove vital. And with nothing else for most of the baseball world to do starting Monday other than look at what the Orioles are going to do and begin the offseason in earnest, the Orioles should be looking at how the last team standing got that way — and seeing whether Cherington's role in all that fits with their vision.