The trade deadline was a major letdown for the Boston Red Sox this year, so the offseason could be the opportunity chief baseball officer Craig Breslow needs to make things right with the fan base.

Boston seemingly put too many of its eggs in the Joe Ryan basket on deadline day. The Sox pursued the Minnesota Twins’ All-Star hard, and depending on who you ask, they may have nearly landed him. But all that mattered was that Ryan stayed a Twin, and the Red Sox’s only starting pitching addition was Dustin May, who wound up pitching six bad outings before hitting the injured list.

This winter, more so than even at the deadline, top-tier starting pitching appears to be a must-have for these Red Sox. It appears Boston may be going right back to the well by trying to pry Ryan from Minnesota.

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Red Sox going after Joe Ryan, part 2

On Monday, CBS Sports’ Julian McWilliams reported that the Red Sox once again plan on going after Ryan this winter, meaning if they haven’t started discussing his name with the Twins, they intend to do so soon.

“Starting pitching stands at the heart of the Red Sox’s needs this offseason,” McWilliams wrote. And, a league source told CBS Sports, Boston plans on re-engaging with the Twins on a possible trade for All-Star Joe Ryan.”

McWilliams also provided a recap of where things fell apart last time, which could be helpful knowledge as Boston attempts to succeed where it once failed.

Initially, the Twins asked for Roman Anthony in the Ryan deal, which was a hard no for the Red Sox. Then they pivoted to prospects Franklin Arias and Payton Tolle and the Sox were ready to play ball.

However, when the Twins countered again and asked for Jarren Duran or Wilyer Abreu, the Red Sox halted, not wanting to pull impact players off their big-league roster. In the end, a deal between the two sides fell apart.

Ryan finished the season with a 3.42 ERA and 194 strikeouts in 171 innings, and a late-season slump probably cost him the opportunity to land Cy Young votes for the first time in his career. But one also could hardly blame him for slumping, as he was essentially pitching for a Triple-A team after the Twins traded nearly every other healthy impact player.

Tolle, Arias, Duran, and Abreu are all still waiting to find out if they’ll don Red Sox uniforms again next season. Will any of them instead head to Minnesota?