1 former Yankees starter Red Sox should target if dream trade rumors fall flat

The 2025 MLB postseason isn't even over yet, and still the Boston Red Sox find themselves mired in rumors for the biggest starting pitchers on the market. Both Hunter Greene and Tarik Skubal have had their names floated by various insiders in recent days, with the Red Sox name-dropped as suitors for either ace, should they truly become available.

That checks out, of course. The Red Sox's lack of impact starting pitching was made painfully apparent in their Wild Card loss to the New York Yankees, and Brayan Bello is probably a little miscast as a No. 2 playoff starter in the current rotation.

The only issue with the plans laid out above: the cost for either Greene or Skubal is going to be prohibitive. Greene is one of the highest-upside young starters in the league with multiple years of team control remaining, and Skubal is about to be a two-time reigning AL Cy Young Award winner. We saw the team balk at the rumored cost for Joe Ryan at the trade deadline, and it's hard to imagine two better pitchers will be handed out for a more reasonable price this winter.

Thus, the Red Sox could turn their immediate attention to a pitcher who is grabbing practically no attention right now: Jameson Taillon. The Chicago Cubs starter is entering the final year of his eminently reasonable deal, and his late-season surge paints the picture of a pitcher the Red Sox can turn into an elite arm in Andrew Bailey's pitching lab.

Jameson Taillon can fix Red Sox's rotation woes as under-the-radar trade target

Taillon flies a bit under the radar as the Cubs' No. 3 starter, but rest assured, he pitched above his billing to close out the 2025 campaign.

Despite dealing with separate calf and groin strains in the second half, Taillon was brilliant after the All-Star break. The former Yankees starter (who has a career 3.46 ERA at Fenway Park) authored a 1.57 ERA in 34 1/3 second-half innings, and opponents slashed just .194/.237/.298 against him. He continued that pace in the postseason, allowing just two runs in eight innings across two starts.

Oh, and he's also one of the pioneers of the kick change, a pitch that the Red Sox have toyed with for some of their right-handed pitchers who struggle against lefty hitters. He'd be a fine mentor to help a few of Boston's young arms learn that offering.

It should also be noted, beyond even the talent cost to acquire Greene and Skubal, the financial burden will be heavy. Skubal is going to demand the largest contract ever for a starter, and Greene will need an expensive new deal at the end of the decade once his current contract expires.

Taillon, on the other hand, is owed $18 million in 2026, the final year of his deal before free agency. As a rental starter without Skubal's résumé, he wouldn't cost an arm and a leg to acquire via trade, and at 35 years old next offseason, he could be re-signed for relatively cheap if the Red Sox want to keep him around a little longer.

So, why would the Cubs deal such a pitcher? Well, their owners, the Ricketts family, are as money-conscious as any big-market owner in the sport, and Taillon's $17 million AAV could be the difference between them re-signing Kyle Tucker or letting him walk.

Likewise, a metric ton of the Cubs' current core (including Taillon) is slated to hit free agency after next season; they could try to cash in on him before he hits free agency in order to restock the cupboards.

There's not nearly as much smoke here as there is surrounding Greene and Skubal, but that's precisely why Craig Breslow would be wise to call up his old team and strike a deal for Taillon, who signed in Chicago when Breslow was still there, by the way. The cost won't ruin other offseason plans, and Taillon could lengthen the rotation as a playoff-tested No. 3 starter.