The Boston Red Sox are fresh off what looks like their first successful trade deadline in years, though the outcome truly remains to be seen. Many former Red Sox — including one Craig Breslow trade deadline addition and one subtraction — were dealt to contenders to help them get ahead. 3 former Red Sox traded at 2026 deadline feature pieces of regrettable Craig Breslow dealsDustin MayRed Sox fans might remember the Dustin May trade forever, and not in a good way. Nathaniel LoweNathaniel Lowe came to the 2025 Red Sox after the trade deadline, following his placement on waivers by the Washington Nationals. Ryan ZeferjahnLike Dustin May, Ryan Zeferjahn was part of another unsuccessful Breslow deadline trade.