Red Sox Eyes: Top Pitching Targets in a Busy Offseason

The Boston Red Sox’s 2023 trade deadline strategy might go down as one of the bigger “what-if” moments in recent team history. Reports say the club nearly landed Minnesota Twins right-hander Joe Ryan, but the deal fell apart at the last minute because of timing issues.

Boston ended up making a smaller move instead — grabbing Dustin May. That decision backfired, leaving fans and analysts scratching their heads.

This episode really shows the Red Sox’s ongoing struggle to find reliable starting pitching. It also highlights just how important it is to act decisively in high-stakes MLB trades.

Boston’s Pursuit of Joe Ryan

Multiple sources say the Red Sox got deep into talks to bring Joe Ryan to Fenway Park just before the 2023 deadline. Ryan had become one of Minnesota’s steadiest starters — exactly the kind of pitcher Boston needed at that moment.

He seemed like the perfect fit for a rotation that desperately needed a boost. A guy who could deliver quality starts down the stretch? That’s what Boston was looking for.

Timing That Killed a Blockbuster

The Twins were reportedly surprised by Boston’s late interest. With only a few hours left before the deadline, Minnesota didn’t think there was enough time to work out all the details.

The talks collapsed. For Boston, missing out on Ryan stung, especially with the postseason looming.

The May Move — and Its Fallout

After the Ryan deal fizzled, Boston quickly pivoted to Dustin May. The hope was that May could eat innings and bring some stability.

That didn’t happen. Not even close.

Struggles on the Mound

May’s time in Boston was rocky. He finished with a 1–4 record and a 5.40 ERA.

Those numbers just didn’t justify trading for him. His struggles got so bad that the coaching staff left him off the Wild Card Series roster against the Yankees.

That move said a lot about the team’s lack of confidence in him when it mattered most.

Early Exit and Bigger Questions

The Red Sox’s playoff run ended sooner than most people expected. A lot of analysts pointed to the deadline decisions as a big reason why.

Boston’s failure to get Ryan, and May’s disappointing stint, just kept the same old question alive: Why can’t they land the right pitchers at the right time?

Free Agency Uncertainty

After the season, May hit free agency. His future in Boston? Totally up in the air.

The Red Sox now face another offseason wondering how to finally get dependable, top-tier starting pitching.

Lessons in MLB Trade Strategy

This whole Joe Ryan saga has a few takeaways for front offices and fans alike. Timing matters just as much as talent in these deals.

When you push late for a big name, there’s barely any time to negotiate, review medicals, or sort out the finances. It’s a risky game.

The Costs of Indecision

In baseball’s trade market, chances can disappear in a blink. By waiting until the last hours to call Minnesota, Boston made it a lot harder to get Ryan.

The result? A less impactful trade, a weaker playoff run, and more pressure to fix the rotation this winter.

Moving Forward: What the Red Sox Need

May has come and gone, and Ryan’s still pitching for the Twins. Boston’s front office has to scan the market again for a starter who fits.

This whole episode really highlights a few priorities for the Sox:

• Decisive action — They’ve got to talk to target teams early, or risk getting stuck in deadline chaos.
• Quality over quantity — Go after arms that actually move the needle, not just another middle-of-the-road guy.
• Rotational depth — The staff needs more muscle to handle injuries and those inevitable slumps.

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Here is the source article for this story: In the market for arms, there’s no shortage of offseason targets for the Red Sox