Last December, the Boston Red Sox pulled off a seismic trade to land an All-Star starting pitcher from the American League Central. Will lightning soon strike twice?

The Red Sox were known to be in hot pursuit of Minnesota Twins ace Joe Ryan at the July trade deadline, and their failure to pry him loose was a huge cause of their disappointing haul — and middling finish down the stretch.

If Boston zeroes in on Ryan as its top target again this winter, which would make a lot of sense given their persisting need for a No. 2 starter, what might it take to succeed where things once went wrong?

Oklahoma’s Kyson Witherspoon (26) throws a pitch during the college baseball game between the University of Oklahoma Sooners and Lehigh at L. Dale Mitchell Park in Norman, Okla., Friday, Feb., 14, 2025. / SARAH PHIPPS/THE OKLAHOMAN / USA TODAY NETWORK via Imagn Images

On Friday, Red Sox insider Jen McCaffrey of The Athletic proposed a potential package comprised of one of Boston’s top two position player prospects (infielder Franklin Arias, outfielder Jhostynxon Garcia), plus first-round pick Kyson Witherspoon, a hard-throwing right-handed pitcher.

“Dan Hayes, The Athletic’s Twins writer, suggested Minnesota would be seeking two top-50 prospects, one with a mid-ceiling and one more of a lottery ticket,” McCaffrey wrote.

“If the Twins want pitching in return, the Red Sox might be more inclined to trade Witherspoon as opposed to Tolle or Early. Arias or Garcia, along with Witherspoon, could be a good start for a deal with Ryan.”

From Boston’s perspective, it’s probably a lot easier to give up Garcia, who is somewhat redundant in the deep outfield mix the Red Sox already have, than Arias, who has Gold Glove potential at a position (shortstop) that’s more up in the air down the road.

However, the need for an arm like Ryan supersedes any minor long-term roster construction tweaks. The first-time All-Star pitched to a 3.42 ERA and put up 4.5 wins above replacement this season, but he was a lot better for most of the year, and it’s easy to excuse him for slumping down the stretch on a team that had completely given up on the season.

This is a “whatever it takes” situation if the Red Sox are serious about bringing in Ryan. Boston’s championship window could be wide-open for the next few years, but only if they continue making bold moves to build a viable roster.

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