The Boston Red Sox missed the postseason for the third consecutive season and desperately need an impact offseason to snap that in 2025. The Red Sox should be on the horizon of that jump back to October next season with the foundational young players established in the big leagues and the highly-anticipated top prospect pool on the cusp of their own debuts. For that reason, Boston should be aggressive this winter, both on the trade market and in free agency, to add legitimate complimentary talent to legitimize the roster to playoff contention. David Ortiz knows plenty about that from his legendary Red Sox career that featured a trio of World Series championships.