Ranking the 5 Best Red Sox Offseasons Since 2000

It’s 2018. The young new year in Boston has been filled with cold weather and relatively no baseball moves.

While we wait, here are my five best offseasons since the new ownership group took over in 2002.

Honorable Mention

2015 – 2016

This was the first year of the Dave Dombrowski era, and he let it be known.

Dave made a few splashes during this offseason. Most notable being the Craig Kimbrel acquisition and signing of free agent LHP David Price.

I am mixed on this offseason.  The one thing preventing me from ranking it a bit higher is David Price. If Price finally pitches to his capability, then this might be Dombrowski’s best overall offseason.

In November of 2015, the Red Sox traded for closer Craig Kimbrel of the San Diego Padres.  The Padres received outfielder Manuel Margot, infielders Javier Guerra and Carlos Asuaje, and left-hander Logan Allen in exchange for the firey closer.

The Kimbrel acquisition has been great. Manuel Margot is an okay player, but nothing that the Red Sox need at this point.

Notable Acquisitions:

RP Craig Kimbrel; SP David Price; OF Chris Young

5) 2005 – 2006

The Beckett/Lowell trade was under scrutiny for much of the 2006 season. Josh Beckett just couldn’t find it, and he gave up a ton of home runs.

However one year later, Beckett finished 2nd for the AL Cy Young award, and Mike Lowell won World Series MVP.

Overall, the trade that defined this winter was a good one for both teams. It got the Red Sox a title and the Florida Marlins a franchise shortstop in Hanley Ramirez. The Red Sox had a parade of shortstops from 2006, all the way up until the Xander Bogaerts era.

Notable Acquisitions:

OF Coco Crisp; 2B Mark Loretta; SP Julian Tavarez; SS Alex Gonzalez; SP Josh Beckett; 3B Mike Lowell

4) 2016 – 2017

Another offseason that saw big trade for a starting pitcher. Our guy Chris Sale.

This offseason saw Dombrowski move a couple huge prospects to the south sidebar of Chicago for the lanky left-hander.

Sale struck out 300+ batters this past season and was nearly untouchable from April-August.

There is only one black mark here and it was the trading of Travis Shaw. Until the call-up of Devers, the Sox had a glaring hole at 3rd base. Travis Shaw would’ve fit exactly what they needed. A left handed power hitting 3rd baseman. Dombrowksi dealt Shaw to the Brewers in exchange for Tyler Thornburg- who didn’t throw a pitch for the Red Sox all of 2017.

We will have to see how Thornburg performs in 2018 to fully judge this offseason properly.

Notable Acquisitions:

1B Mitch Moreland; RP Tyler Thornburg; SP Chris Sale

3) 2012 – 2013

I loved this one. Bobby Valentine was fired, Daisuke’s contract was up, and the Red Sox filled their roster with a bunch of grit and heart.

Most importantly, the Red Sox needed a manager. Cherington and company sent Mike Aviles to Toronto in exchange for their manager- John Farrell.

I remember watching this offseason unfold and being so mixed on it. Victorino, Napoli, Uehara. It was tough to look at these guys at the time and see anything more than average.

We all know how well these guys performed the following year, giving the Red Sox their 3rd championship in 9 years.

Overall, the Red Sox spent $126 million and the only questionable addition during this winter was probably Ryan Dempster.

Notable Acquisitions:

C David Ross; OF Jonny Gomes; OF Shane Victorino; RP Koji Uehara; 1B Mike Napoli; SP Ryan Dempster; SS Stephen Drew

2) 2003 – 2004

For me, this was so close to being number one. I absolutely would not hate you if you put this offseason as the best one in Red Sox history, let alone of the John Henry era.

The wound of Aaron Boone’s game 7 walkoff home run was still fresh. Nonetheless, the Red Sox had to get down to business.

This offseason had everything. Tito took over for Grady Little, Curt Schilling and Theo Epstein ate Thanksgiving dinner together, and the Sox got their closer in Keith Foulke.

After this very successful winter, the Red Sox won their first World Series title in 86 years.

Notable Acquistions:

INF Pokey Reese; 2B Mark Bellhorn; RP Keith Foulke; SP Curt Schilling; Manager Terry Francona

1) 2002 – 2003

For starters, new owner John Henry and the Boston Red Sox hired Billy Beane as their general manager, only for Beane to immediately resign and go back to Oakland.

Needing a back up plan, the Red Sox announced the hiring of Brookline native Theo Epstein. I look at Theo as quite possibly the greatest baseball executive of my generation.

Not only did the Red Sox acquire their brain, they also acquired their heart.

On January 22nd, the Boston Red Sox signed David Ortiz to a non-guaranteed contract worth $1.25 million. Ortiz was a free agent following his release from the Twins. Ortiz went on to lead his team to three world championships.

Kevin Millar was also added this offseason, thus giving birth to a team identity that will forever live in baseball history.

Oh, also, Bill Mueller won a batting title. The Red Sox seemingly hit on every move this winter.

Notable Acquisitions:

3B Todd Walker; 1B/OF Kevin Millar; 3B Bill Mueller; 1B/DH David Ortiz


Dishonorable Mention: 2011 – 2012

The worst. I almost chose 2010-2011, which saw Adrian Gonzalez and Carl Crawford come to Boston.

I had to pick this one, though.

The Red Sox lost their general manager in Theo Epstein, their captain in Jason Varitek, their closer in Jonathon Papelbon, and finally, fired the greatest manager in Red Sox history- Terry Francona.

The Red Sox replaced their superstar manager with the worst skipper Yawkey Way has ever seen. None other than Bobby Valentine.

Dumpster fire.

This offseason also saw the putrid trade of Andrew Bailey for Josh Reddick. Josh just won his first World Series title this past October.

There you have it.

Here’s hoping that Dombrowksi does something a little more exciting than just re-signing Mitch Moreland this winter.


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