Ryan Dempster has Dustin Pedroia stories
The Red Sox's blueprint heading into last year's winter meetings wasn't difficult to decipher. Try to get Juan Soto, and if you don't get him, move on to Alex Bregman, while also zeroing in on Max Fried or Garrett Crochet to fill their top-of-the-rotation void.
This year the path has been a bit more unpredictable.
Case in point: The Red Sox's trade for Johan Oviedo Thursday.
The five-player deal highlighted by Jhostynxon Garcia going to Pittsburgh and Oviedo coming back was anything but the straight line to filling out the roster many were surmising. What this represented was the Red Sox's conviction in evaluating potential rather than leaning on here-and-now certainty.
They believe Oviedo can be the kind of top-of-the-rotation pitcher that would cost a whole lot more than Garcia if already proven. It's the same line of thinking that drove the Sonny Gray deal.
And a case can be made.
The 27-year-old (who turns 28 on March 2) is under team control for the next two years, having made $2 million last season. After showing signs of a breakout year in 2023, he missed all of 2024 with Tommy John surgery and a good part of 2025 due to a lat injury.
He is the type of pitcher and presence who screams potential, standing at 6-foot-6, 275 pounds while owning one of the best pitching extensions (98th percentile) in the big leagues.
Oviedo is primarily a fastball/slider pitcher, using the pitches a combined 69 percent of the time during his nine starts last season. (He didn't debut in 2025 until Aug. 4.) The fastball, which has averaged about 96 mph, got a 31.3 whiff rate while holding opponents to .149 batting average.
The righty was extremely solid once jumping into the Pirates' rotation last season, finishing with a 3.57 ERA, with opponents hitting just .182 with a .642 OPS. He also excelled in his three matchups against AL East teams, giving up one run in five innings against Toronto, two in five frames at Fenway, and a pair of runs over 5 2/3 innings vs. the Orioles.
The Red Sox viewed it as necessary to upgrade the spots just behind Crochet. Hence, Gray and now Oviedo.
Such an approach seems more uncertain than the one taken by Toronto, which aggressively went after their top-of-the-list free agent starter in Dylan Cease (who the Red Sox weren't a finalist on). The question the Sox were asking themselves was whether the duo they ultimately acquired to team with Crochet and Brayan Bello is as much of a solution as the likes of free agent names after Cease and Framber Valdez, such as Michael King, Zac Gallen, and even Tatsuya Imai.
There are still what-ifs about Joe Ryan's availability, who would undeniably represent the certainty many believed Craig Breslow was referencing when announcing his offseason agenda in Las Vegas. But there is continued skepticism throughout baseball that the Twins will deal Ryan this winter.
Another element of this approach by the Red Sox is that by getting two pitchers they believe can emerge into big parts of the solution, it frees them up to use some very viable major league arms to potentially get their big bats if the asking prices for Pete Alonso, Alex Bregman, and Bo Bichette get too outrageous.
As one American League East executive said, the Red Sox have put themselves in a position few teams can claim thanks to a list of major league-ready pitchers that stretches well beyond No. 5 or 6. It's why the Blue Jays had to prioritize paying Cease and KBO standout Cody Ponce.
But when it comes to this trade, make no bones about it: They view Oviedo as far from more than a depth option. While there are conflicting opinions on Garcia's ceiling in the big leagues, he still represented a valued trade chip, one they have now used in something other than a deal for Ryan.
As the winter meetings get ready to kick off, basically Sunday night, we wait for the next move. Most are seeing the position player free agent market dragging, with one executive surmising Bichette might not make his decision until January. That means the Red Sox are going to figure out how long they should wait before solving their problems via trades rather than waiting on the big free agent names.
If we have learned one thing this offseason so far, it's that predicting Breslow and Co. has become a challenging proposition.