In the two weeks preceding MLB’s annual Winter Meetings in Orlando, the Boston Red Sox swung trades for a pair of right-handed starting pitchers.

After acquiring veteran Sonny Gray from the St. Louis Cardinals before Thanksgiving, the Red Sox made a deal with the Pittsburgh Pirates Thursday evening for Johan Oviedo, lefty reliever Tyler Samaniego, and minor league catcher Adonys Guzman. (By some odd coincidence, the Pirates acquired Oviedo from the Cardinals during the ‘22 season.)

Here are some of the angles and implications of these trades, particularly the second, for the Red Sox as they prepare for a frenetic week in Florida.

Breaking ball time in Boston

Gray and Oviedo both bring strong breaking-pitch acumen to Boston, but the former is firmly established and arguably one of the more underrated pitchers of the last decade, while the latter is a work in progress.

Prior to the Tommy John surgery that cost him the entire ‘24 season, Oviedo ranked in the 98th MLB percentile in Breaking Run Value in ‘23. The minus-5.2 vertical drop on his fastball, however, ranked ninth-worst in baseball that year (though not worse than Tanner Houck’s minus-6.1).

Oviedo returned this year with significantly-improved vertical drop (minus-0.3), albeit in a significantly smaller sample size.

Password changed

Jhostynxon ‘The Password’ Garcia was the key return in this trade, but it makes sense that the Red Sox dealt him now. Even if they ultimately parted with Jarren Duran or Wilyer Abreu (or Ceddanne Rafaela) this offseason, Garcia would not be the next man up. The Red Sox need to create space for Roman Anthony, the new face of the franchise, who had to split time between the outfield and designated hitter last summer due to their various roster logjams.

Garcia now has the opportunity for an everyday role in Pittsburgh.

Is the depth getting better?

It’s a mark of their newfound pitching depth that the Red Sox are not only able to part with pitchers, but have arms other teams actually want.

Since the offseason began, they’ve traded several major- and minor-league pitchers, including stalwart lefty reliever Brennan Bernardino, lefty Chris Murphy, and righty reliever Luis Guerrero. Thursday’s trade forced them to designate reliable swingman Cooper Criswell for assignment, and the New York Mets claimed him off waivers Friday.

They’ve acquired pitching as well, but their intake has leaned heavily toward position players, such as infielder Tristan Gray and several minor league catchers.

Are the incoming pitchers and upcoming pitching prospects better than the arms with whom they were willing to part? Bernardino, in particular, was a significant contributor the last two seasons, pitching 57 and 55 games, respectively.

Red Sox gamble with depth and lose as Mets claim Criswell off waivers

Implications for Winter Meetings and beyond

Trading for starters with two years of club control apiece – Gray has a team option for ‘27 and Oviedo has two years of arbitration eligibility remaining – enables the Red Sox to shift financial focus to free agent position players at the Winter Meetings. In particular, a right-handed slugger for a lineup in desperate need of power.

The Red Sox could also still deal from their starter surplus, though at present, it’s unlikely they feel secure enough with Oviedo to winnow their depth too much. His arrival is somewhat similar to how the Red Sox viewed lefty Kyle Harrison when they acquired him in the Rafael Devers trade this year: someone with potential who needs significant recalibration and honing before he can be a legitimate contributor down the road.

Oviedo has more big-league experience than Harrison, but the Red Sox will want to see him stay healthy, lower his walk rate, and continue fine-tuning his fastball. He does not need to do that in the majors, either; he has a remaining minor league option, so the Red Sox could have him start the season in Triple-A Worcester. However, Oviedo is only 93 days of service time away from the five-year threshold, and will then have the power to refuse such a demotion.