Why the Red Sox should make this risky trade ahead of non-tender deadline

Will Craig Breslow's first deal as the head of the Red Sox front office be a high-risk/ high-reward trade?
Milwaukee Brewers starting pitcher Brandon Woodruff
Milwaukee Brewers starting pitcher Brandon Woodruff / Rich Storry-USA TODAY Sports

The Boston Red Sox are in the market for pitching this offseason. Newly appointed president of baseball operations Craig Breslow will be scouring the free agent market this winter with an eye toward upgrading Boston's rotation.

But what if Breslow wanted to play the long game? According to MLB Network's Jon Morosi, an intriguing trade candidate has emerged with less than 12 hours remaining until the non-tender deadline.

According to Morosi, the Milwaukee Brewers are discussing Brandon Woodruff in trade conversations with multiple teams. Are the Red Sox one of those teams? Should they be?

Why are the Brewers trying to trade Brandon Woodruff?

Brandon Woodruff is a two-time All-Star with a career-ERA of 3.10 and 788 punch outs over his seven years in the big leagues. So why are the Milwaukee Brewers even considering trading Woodruff a year after winning the NL Central?

That's where the trade discussions get risky. Woodruff only pitched in 11 games last season and ended the year on the injured list after undergoing shoulder surgery to repair the anterior capsule in his right shoulder.

While Woodruff sees himself returning to the mound during the second half of the 2024 season, conservative estimates might suggest that the 30-year-old will miss the entire season.

Woodruff is also in the final year of arbitration with Milwaukee. According to MLB Trade Rumors, Woodruff is expected to earn $11.6 million next season. That's quite the payday for a pitcher who may not set foot on a major league mound.

Why the Red Sox should trade for Brandon Woodruff ahead of non-tender deadline

If the Boston Red Sox were to engage with the Milwaukee Brewers in trade talks surrounding Brandon Woodruff, there are two schools of thought as to why. First, it's assumed that Woodruff will return after the All-Star Break and can contribute in some capacity next season.

The second, and more likely option, is that the team that completes the trade for Woodruff works out a two-year contract extension that effectively protects the club in the event that the pitcher's entire 2024 campaign is wiped out. The deal would also offer guaranteed money to the player in 2024 and 2025.

The Boston Red Sox used this same strategy with James Paxton. After undergoing Tommy John surgery in spring of 2021, the Red Sox took a flier on Paxton during the following offseason and inked the southpaw to a one-year contract with an option for the 2023 season.

Paxton would not throw a single pitch for the Boston Red Sox in 2022, but returned to the mound this past season and won AL Pitcher of the Month honors in June. Paxton finished the year going 7-5 with a 4.50 ERA.

Trading for Brandon Woodruff would be a risky move on the part of Craig Breslow, but it's one that could certainly pay off heading into the back-half of next season or even 2025. The Red Sox should, at the very least, kick the tires on a potential deal for Woodruff before the non-tender deadline.