Do Dave Dombrowski's Trade History, Current Market Mean Red Sox Blockbuster Coming?

It’s been a relatively quiet offseason for the Boston Red Sox, but don’t be surprised if that changes soon.

Major League Baseball avoided any sort of prolonged labor issue by coming to terms with the players’ union on a new collective bargaining agreement Wednesday night, essentially lighting the hot stove.

Additionally, the winter meetings begin Sunday, meaning teams are ready to open for business.

The Red Sox don’t have a pressing need for major upgrades as they did a year ago, when president of baseball operations Dave Dombrowski acquired a No. 1 pitcher (David Price) and closer (Craig Kimbrel). Boston won the American League East this season and is well positioned for more success moving forward.

However, the Cleveland Indians swept the Red Sox out of the American League Division Series, a clear indication the club isn’t where it or its fans want it to be. Which brings us to the offseason.

In his previous stops with the Montreal Expos, Miami Marlins and Detroit Tigers, Dombrowski displayed a willingness to wheel and deal during the offseason. He’s made more than 30 offseason trades during his career, most recently landing Kimbrel in a big move last November.

Don’t be shocked if there’s another significant deal looming. There are all the makings for another big Dombrowski blockbuster.

The Red Sox are a good team, but in order to be great, they need to add starting pitching depth. There’s one small problem, of course: This free-agent starting pitching market is horrendous.

Rich Hill, the best free agent pitcher, will be 37 on Opening Day, and his career-high in innings (195) came 10 years ago. He’s logged just 292.1 innings in nine combined seasons since. The cupboard, you could say, is bare.

If Dombrowski and the Sox want to add a legitimate starting pitcher, they must do so via trade. Frontline starters like the Chicago White Sox’s Chris Sale, Oakland A’s right-hander Sonny Gray or even Detroit’s Justin Verlander come to mind, but they won’t come cheap. Those teams know the market is thin, therefore allowing them to drive up the price. And if those sorts of pitchers aren’t moved this winter, their clubs can hold off and wait until the trade deadline, where they can take advantage of teams hoping to add a top-of-the-rotation starter for the stretch run.

Will Dombrowski take the plunge and make a big deal? If his history is any indication, he certainly won’t shy away from doing so.

Here’s a small sampling of what Dombrowski has done over the winter in recent years.

Dec. 11, 2014
Detroit acquires: Yoenis Cespedes, Alex Wilson, Gabe Speier
Boston acquires: Rick Porcello

Still with the Tigers, Dombrowski needed an outfielder and made a great call in getting Cespedes, who was a 4-win player in just 102 games with the Tigers. Giving up Porcello wasn’t ideal, but the Tigers eventually turned Cespedes into 2016 American League Rookie of the Year Michael Fulmer via a draft pick, which is pretty good.

Nov. 20, 2013
Detroit acquires: Ian Kinsler, cash
Texas acquires: Prince Fielder

In another bold move, Dombrowski sent Fielder and his enormous contract in a trade that not only netted Kinsler — an All-Star and Gold Glove winner since being acquired — but also freed up first base, allowing Miguel Cabrera to move across the diamond from third base to a less taxing position.

Dec. 8, 2009
Detroit acquires: Phil Coke, Austin Jackson, Max Scherzer, Daniel Schlereth
New York Yankees acquire: Curtis Granderson
Arizona acquires: Edwin Jackson, Ian Kennedy

Why make a two-team trade when you can make a three-team swap? All things considered, Dombrowski and the Tigers made out like bandits in acquiring Scherzer, a future Cy Young winner. The other three all contributed at the major league level, highlighted by Coke who appeared in 299 games over five seasons in Motown.

Dec. 5, 2007
Detroit acquires: Dontrelle Willis, Miguel Cabrera
Miami acquires: Andrew Miller, Burke Badenhop, Cameron Maybin, Dallas Trahern, Eulogio DeLaCruz, Mike Rabelo

If you’re a Red Sox fan, this one should make you feel really good about Dombrowski’s potential this winter. Cabrera has provided the Tigers with a staggering 51 wins above replacement since this 2007 blockbuster, winning two MVPs and staking his claim as one of the greatest right-handed hitters of the last 25 or even 50 years. And while his success in the 2016 playoffs makes Miller stick out like a sore thumb, it took him four or five years (and a move to the bullpen) after the trade to really become the pitcher we know him as today. Other than that, Dombrowski gave up relatively nothing to acquire one of the greatest players of this era.

There’s also the chance Dombrowski looks to shed some payroll this winter. While a trade for a pitcher like Verlander obviously would come with a lot of financial responsibility, the Red Sox could opt to go a different direction. We’re not saying Boston will sell this offseason, but the Red Sox might be smart to listen to deals on their own pricey veterans, especially given the latest luxury tax threshold changes in the newest collective bargaining agreement.

Has Dombrowski had some misses over the years? Sure. Any baseball executive — especially at the volume which he deals — will have a misfire, and Dombrowski’s no different. But this is what the Red Sox hired him to do.

There’s certainly reason to believe he’ll be busy this winter, and the track record, on the whole, should encourage Red Sox fans.