Red Sox future and the fleeting window to win now

Has Dave Dombrowski really put the Boston Red Sox in the best position to win? Or has he set this franchise up for a dark, gloomy future?

Dave Dombrowski has shown tendencies throughout his career of doing absolutely anything to win now. He definitely did not sway from his ways when coming to the Boston Red Sox during the 2015 season.

Dombrowski made his mark in Boston almost immediately, trading for Craig Kimbrel, one of the leagues most feared closers, and signing David Price to a seven-year, $217M deal (includes opt out in 2018). Price was coming off an All-Star year, finishing 2^nd in the Cy Young voting behind Dallas Keuchel, who had a 7.2 WAR (Price had a 6.0 WAR). These were two very high-profile players who could make an immediate impact and improve the team.

If this was not enough of a statement in his first year with the program, he also traded one of our brightest pitching prospects Anderson Espinoza, who draws comparison’s to the likes of Pedro Martinez, for Drew Pomeranz, a move that I believe marked the beginning of the “Dealin’ Davey” Era.

After trading one of our most highly touted prospects, Dombrowski showed that he wasn’t afraid to trade ANY of the team’s top prospects if it meant giving the team what he believed to be the best chance to win right now.

This past offseason, he proceeded to trade two MORE of our best prospects, Yoan Moncada (the top prospect in all of baseball) and Michael Kopech (a fiery right-handedd starting pitcher), plus two other players for Chris Sale. Now, don’t get me wrong, Sale is an absolute freak. Whenever he pitches it is appointment television to watch, just as a fan of the game. But the Red Sox farm system went from being rich with future talent, to almost nothing. Dombrowski continued to communicate that the Red Sox are trying to win a World Series now, but the problem with his strategy is we are just not winning.

The Shrinking Window and “The Problem”

For the second year in a row, the Red Sox were bounced from the ALDS after winning the AL East, this time by the eventual World Series champion Houston Astros. So what is different from last year and 2016? Not much expect for the fact that the Red Sox window to win is now a year shorter.

The following are the list of players who could be playing for different teams by the 2020 season: David Price, Craig Kimbrel, Drew Pomeranz, Hanley Ramirez, Rick Porcello, Mitch Moreland, Xander Bogaerts, Chris Sale. With many of our high profile players coming off the books, and the trading of our farm system including Moncada, Kopech, and Espinoza (to name a few), it seems the Red Sox have until 2020 to win a World Series in order for Dombrowski’s stint in Boston to be a success.

To make things harder for the Red Sox and Dombrowski, the New York Yankees, who were supposed to be in a “rebuilding year” this past season, have found a young core of players who look determined and ready to make a serious run at contending for a World Series as soon as next year (Gary Sanchez, Aaron Judge, Luis Severino). Some may say that the Yankees are creating a dynasty in front of our eyes. Include the addition of Giancarlo Stanton and his 59 homeruns, and the Red Sox have what we call a problem.

I believe that Dombrowski was not preparing for the  Yankees to be a threat to the Red Sox for at least a couple more years, and this has put a huge wrinkle in his plans and future for this team.

How to compete

So the question is, what is Dombrowski going to do in order to compete with the likes of the Yankees and the Astros?

It’s clear that the Red Sox need a power bat, finishing 27^th in the league in home runs. If the past is any indication for the future, Dave Dombrowski is looking to fill the needs of the Red Sox with the best option available (see Price, Sale, Kimbrel). All signs point towards the signing of J.D. Martinez, though it seems Dombrowski and Scott Boras (Martinez’ agent) are currently in a stand-off.

On MLB Network Radio on Sirius XM, Dombrowski stated that he is comfortable with the team the way it is now, stating that he is expecting players from the organization will have much better offensive years. Dombrowski also includes that getting the starting pitchers back and keeping them healthy will also be helpful for the team.

On the other side, Boras seems to be willing to wait Dombrowski out. It has been reported by Jon Heyman of FanRag Sports that Martinez is willing to hold out until Spring Training, and recently that the Red Sox have offered Martinez a deal in the range of 5 years, $100 million.  With an offer on the table, and Dombrowski saying he is content with the way the team is, it is very possible that the Red Sox will wait until next year to add the big bat they so desperately need.

The Monster Class

If the Red Sox choose to wait till next year for one of the most prolific free agent classes that MLB has ever seen, that is yet another year of the Red Sox window wasting away. This is not even considering that Boston has become an un-desirable destination for prospective players to call their home, which includes some of the toughest media in the league.

More from Red Sox News

• How realistic are the Boston Red Sox/Chris Sale trade rumors?
• Giants’ desperation post-Carlos Correa debacle highlights Red Sox’ lack of urgency
• Dave Dombrowski reunites with former Red Sox ace on Phillies
• 10 grievances against the Boston Red Sox in honor of Seinfeld holiday Festivus
• Red Sox risk repeating rookie mistake with Eric Hosmer release

It seems they will not be able to sign Bryce Harper, as most signs point to him eyeing the Chicago Cubs, and if anyone realistically thinks that Manny Machado would play in Boston after not only the situation that occurred with him and Dustin Pedroia, and the racial remarks that have been made towards Adam Jones at Fenway Park, they are probably not paying attention.

After those two blockbuster names, the next best power bat available will be Josh Donaldson (32). The argument that can be made against Martinez (age 30 and injury risk), can also be made with Donaldson, who will be entering his age 33 season in 2018, and played 113 games this past season due to a calf Injury.

If a big bat is what Dombrowski is looking for, and it is what the Red Sox need NOW in order to win, then it seems Martinez may be our best option.

Next: Free agency mistakes won't dictate Martinez market

So, what’s next?

It will be interesting to see what Dombrowski will do the rest of this offseason, and for that matter, the next two offseasons as well. Will he trade even more of our remaining prospects (Chavis, Groome, Devers, Bennintendi, Travis) in order to “Win now”? Is he going to leave the Red Sox with a bunch of aging, washed up players, and depleted farm system? Looking at how he has left franchises in the past, this is a possibility (Florida Marlins, Detroit Tigers). Has Dombrowski really put this program the best position to win, or has he set up this program for a bleak future? Only time will tell.