Chicago Cubs President of Baseball Operations Theo Epstein has been in the role of 'offseason winner' before when he was general manager of the Boston Red Sox prior to the 2011 season.
After trading Anthony Rizzo for Adrian Gonzalez and signing Carl Crawford to a huge contract, the 2011 Red Sox were being dubbed as one of the best of all time.
"Expectations got so high," Epstein told CSN Chicago. "People were speculating: 'Is this the greatest team of all-time? A super-team? An uber-team?'"
Instead of living up to expectations, the 2011 Red Sox had a horrendous start, but recovered by August leading the AL East only to have a monumental collapse in September that cost manager Terry Francona his job. Along with the disappointment in Boston that season, Epstein left for the Cubs that October.
"It is an unbelievable dynamic the last few years," Epstein said, "how the winners of the offseason tend to be miserable the following September."
After several years of building the Cubs en route to a surprising appearance in the National League Championship Series in 2015, Epstein now has his team in place to improve on a 97-win season. Bringing in John Lackey, Ben Zobrist, and Jason Heyward, along with bringing back a top-notch, young overall roster, have many dubbing the Cubs as the 'offseason winners' with a World Series win possible.
"The bigger target, the greater pressure, I think, equals a grander chance for success. So I'm all about that, and I definitely will bring that to our guys' attention," manager Joe Maddon said during the winter meetings. "(With) the accountability of our young players -- combined with our veterans -- I really believe we could avoid those kind of pitfalls."
Despite the major additions to the roster made this offseason, the Cubs managed to not sell the farm to get the pieces they needed. Instead of going for the splashy trade, Epstein and the Cubs managed to build around the young talent while making Chicago and Wrigley Field the 'place to be' as the club tries to beak it's long championship drought.
"Organizations that are the healthiest, (with) the most talent coming through the pipeline, the fewest holes, the most areas of surplus and depth, tend to have the least active offseasons. And those organizations tend to win," Epstein said. "It means they're doing something right. It means they have ways to address their needs internally. It means they have a lot of talent spread out in different areas of the organization. The teams that sometimes quote-unquote 'win the offseason' do so in response to a glaring need to infuse talent in a number of different areas."
Overall, according to Epstein, building a true contender cannot be accomplished in one offseason, rather it is a long process of that can take years to reach ultimate goals.
"A healthy organization is not made by virtue of one busy offseason. It's really years and years and years of planning, hiring scouts and development people and putting processes into play and seeing that approach manifest over time."
