For much of John Henry's tenure as owner of the Red Sox, the team has avoided handing out lengthy, high-priced contracts to starting pitchers. While Boston hasn't altogether eschewed hefty investments for starters under Henry (John Lackey and Daisuke Matsuzaka were both paid handsomely, after all), the organization has largely been reluctant to commit big money to veteran hurlers, especially of late.
The most notorious example of this prudent approach is, of course, the club's choice not to extend Jon Lester in 2014 and allow him to enter free agency last offseason. During the 2015 campaign, at least, the decision to let Lester walk backfired. The Red Sox's pitching staff missed that type of stable and dominant presence atop the rotation, while Lester helped carry the Cubs to a surprise trip to the NLCS.
Yet even after the team brought in Dave Dombrowski to lead the front office and vowed to add an elite pitcher to solidify the rotation this winter, how Boston would go about finding that top arm was anything but clear. Many observers, noting Henry's reluctance to invest heavily in aging starters, felt Dombrowski would deal from the organization's stable of talented prospects to land an ace.
As the offseason has begun, however, it's looking increasingly likely that Henry will finally open his wallet and spend big on one of the marquee names in free agency. In the days following the club's trade for Craig Kimbrel, Dombrowski himself has stated that he'll now likely acquire a starter on the open market. And although plans can change quickly, these reports from Ken Rosenthal and Tom Verducci also indicate Boston is ready to make a big investment in a starting pitcher:
Tom Verducci on MLB Network said, "I believe David Price is going to Boston. Dave Dombrowski is all in." #RedSox
— Joon Lee (@iamjoonlee) November 23, 2015
Given Rosenthal and Verducci's reputations, we can be pretty certain those statements are an accurate reflection of how seriously the Red Sox are pursuing the likes of David Price and Zack Greinke.
The big question in all this is why has so much changed from last offseason to this one? Why have the Red Sox suddenly gone from being unwilling to spend heavily on veteran starters to supposedly "outbidding" everyone else on Price and Greinke?
While we can't know the organization's thinking exactly, there are many reasons why this winter represents a worthwhile time for Boston to hand out the type of pricey contract its top brass has long avoided.
1. The strength of the free-agent class
Rarely is there so much talent available to teams on the open market, and that goes especially for this year's crop of free-agent starting pitchers. Beyond Price and Greinke, Johnny Cueto and Jordan Zimmermann could improve just about any rotation, and Jeff Samardzija and Scott Kazmir both stand as solid mid-tier options.
Perhaps even more significant, though, is how weak next year's free-agent group is shaping up to be, as others have noted. Stephen Strasburg is the only starter set to hit the open market with top-of-the-rotation potential, and even he comes with plenty of doubts.
If the Red Sox are going to make a large commitment to someone to lead their rotation, waiting until next offseason makes little sense. The time to strike is now.
2. Price and Greinke are both better than Lester
Lester is one of the best pitchers in franchise history, and considering he began his career with the organization, he's a sentimental favorite of sorts. But both Price and Greinke are legitimately better than Lester and, in many ways, smarter bets to age more gracefully and live up to their massive price tags.
Since the start of 2012, Greinke ranks second among all pitchers in ERA behind only Clayton Kershaw (Price ranks fourth). Despite turning 32 in October, many have pointed to Greinke's smarts, elite command and deep arsenal of plus pitches as reasons why he should continue excelling in the years ahead. He put together what was likely the second best campaign of his career in 2015.
Price, meanwhile, is a well-known commodity for the Red Sox given all the time he's spent pitching within the AL East. His injury record is largely spotless, with Price having thrown at least 180 innings in six straight seasons. Moreover, his ability to generate whiffs both inside and outside the strike zone demonstrates he's not headed for a sharp decline in performance any time soon.
Outside of Kershaw, there aren't any better bets in baseball right now than Price and Greinke.
3. Three last-place finishes in four years
Even beyond the two reasons listed above, Boston's woeful on-field performance is probably the biggest motivation behind ownership's willingness to spend more freely on pitching. Despite that 2013 World Series win, the last four years have brought unprecedented levels of losing compared with the franchise's overall track record under Henry's ownership. You better believe that yet another uncompetitive season provided an impetus to improve a roster that's built to win now.
After all, the decision to hire Dombrowski and, subsequently, part ways with Ben Cherington portended that a change in approach was coming. That ownership is giving Dombrowski more freedom and financial leeway than Cherington ever received is a bit baffling, but perhaps Henry felt new leadership was needed before the Red Sox altered their team-building strategy.
What's clear is Boston will be adding a frontline pitcher to the rotation this offseason, and the team is prepared to spend heavily to do so.
There's no denying that signing either Price or Greinke would make Boston much better in 2016. Whether Henry and the Red Sox ultimately regret investing so much in an aging starter a few years from now is another matter.