Red Sox: Why Boston could be back in contention sooner than you think

The Red Sox might be in a better position than we think

As the Red Sox prepare to begin a new shortened season, it seems as good of a time as any to take a look at what to expect from them in the upcoming years.

To most people, the outlook seemed pretty grim for the Red Sox at the end of the 2019 season. They had just finished up a disappointing campaign in which they missed the playoffs. Their payroll was through the roof and had the worst farm system in all of baseball. None of their options seemed very promising.

If the Red Sox kept the team together or tried to fill some of their needs through trade or free agency, they would have been hit with harsh luxury tax penalties. Plus, any season in which the Red Sox don’t at least reach the ALCS is considered a failure, just ask John Farrell. Taking such a hit from the Competitive Balance Tax for a season that had a small chance of success would not have been a wise decision.

A quick rebuild wouldn’t have been realistic either. Many important players such as Mookie Betts, Jackie Bradley Jr., Brandon Workman, and J.D. Martinez (opt-out) were set to hit free agency after the 2020 season. Besides, with Boston’s barren farm system it would likely have taken many years to develop major-league ready prospects.

So the Red Sox were in a bit of a bind.

Fortunately, the organization has been in this situation before―and relatively recently too. The 2011 season ended in a similar fashion: no playoffs, mediocre farm system, new GM and manager.

According to Alex Speier in Homegrown, the team planned to rebuild over the next two to three seasons. They would focus on identifying young talent and developing prospects. From 2014 to 2016, those players would begin to assimilate into major league roles. By 2016, those players would have formed the core of the Red Sox, and they would be ready to make a run at a championship again.

GM Ben Cherington began by trading the three highest contracts on the team: Adrian Gonzalez, Carl Crawford, and Josh Beckett. However, a big market team like Boston does not rebuild in the same way the Kansas City Royals or Miami Marlins do.

The Red Sox are expected to win every year. As a result, Cherington needed to find a way to keep the team afloat while grooming his prospects. He opted to sign veteran players to small-market deals to fill holes in the roster.

This worked better than anyone could have ever expected in 2013. Cherington hit on almost all of his free-agent acquisitions, bringing in Mike Napoli, Stephen Drew, David Ross, Jonny Gomes, Shane Victorino, and Koji Uehara.

This assorted set of unwanted veteran players, along with longtime Red Sox leaders such as Dustin Pedroia, Jon Lester, and David Ortiz beat their 75/1 preseason odds and led the Red Sox to their unprecedented third World Series championship of the new century.

But relying on low-cost sleeper candidates to fuel your team is a very hit-and-miss strategy. And while Cherington hit big in 2013, he missed big the next two years. Grady Sizemore, A.J. Pierzynski, Justin Masterson, Wade Miley, and Allen Craig all turned out to be busts.

He tried to take a stab at making high-cost deals for star players too, only to have each of them go down in infamy. Rusney Castillo, Pablo Sandoval, and Hanley Ramirez became some of the most expensive mistakes in Red Sox history.

In August of 2015, Dave Dombrowski was hired as the Red Sox President of Baseball Operations.

Many thought this was a result of Cherington causing the Red Sox to finish last in the AL East for two consecutive seasons. However, that is not true. In June of that year, principal owner John Henry stated that he was going to be the general manager of this club for a very long time. Even after Dombrowski was brought in, Henry expressed his desire for Cherington to stay with the team.

Going first-to-worst-to-worst is usually an indication of a team that has fallen completely off the rails. This was not true for the Red Sox. Although their performance in 2014-2015 was far from ideal, things were still mostly going according to plan. Cherington’s young players were ready to lead a contending team.

Xander Bogaerts had won a Silver Slugger, Mookie Betts had received MVP votes, and former first-round pick Jackie Bradley Jr. was finally able to find consistency. Prized lefty arm Eduardo Rodriguez was showing flashes of brilliance, while Yoan Moncada and Andrew Benintendi lurked in the minors, ready to contribute to a potential playoff push.

You see, Dombrowski is not necessarily a “better” general manager than Cherington. Both had won the same number of championships at the time. Cherington was a master at developing prospects and was perhaps better at finding low-cost breakout players.

But few people in the game of baseball can put the final pieces of a championship team together like Dave Dombrowski, and when he was unexpectedly fired by the Tigers in 2015, the Red Sox saw an opportunity they could not pass up.

And even being a part of a storied franchise with a long history of success, the front office built one of the most dominant three-year stretches in franchise history.

Cherington had built a core of young players who were on their rookie contracts, allowing Dombrowski to go out and spend large amounts of money to bring in top free agents, like David Price and J.D. Martinez.

Armed with one of the best farm systems in baseball, Dealin’ Dave was able to bring in Chris Sale, Craig Kimbrel, and many other important pieces. The Red Sox won three consecutive division titles, capping it off with a franchise-record 108-win season and a World Series championship.

But Dave left the organization the same way Theo Epstein did in 2011, with a depleted farm system, an underachieving team, and a boatload of contracts to pay.