Yankees battling Red Sox for trade deadline reunion with Gerrit Cole's friend

When the Yankees had the ability to obtain right-hander Jameson Taillon from the Pittsburgh Pirates back in 2021, they knew they were receiving a former top prospect whose solid MLB production had never quite matched his pedigree, with injuries getting in the way. They relied heavily on Gerrit Cole's assessment of his ex-teammate and close friend, ultimately pulling the trigger on a deal that included four players who haven't exactly been missed in the Bronx.

Taillon's two years of team control were solid if unspectacular, but Cole's assessment was likely appreciated. The righty, who battled issues throughout his Pirates career, avoided major injury, making 29 and 32 starts in his two seasons with the Yankees. When the dust settled, he was distinctly average, posting ERA+ marks of 100 and 101 in those campaigns. There was value there, but the Yankees' decision to let Taillon walk to Chicago on a four-year, $68 million contract was widely lauded, even if it left a void in the clubhouse and some uneaten innings.

And yet ... here we are again. According to Bob Nightengale, both the Yankees and Red Sox are interested in adding Taillon if the Cubs decide to bite the seller bullet. It would be out of character for the modern Red Sox to absorb so much money, and it seems fair to wonder if they'd be willing to include a higher-tier prospect to tempt the Cubs into making a deal they'd rather not dabble in.

The Yankees? Nothing is more in character for them than soaking up money as a player ages, except maybe listening to their stars (like Cole) on personnel moves. This tracks.

Yankees, Red Sox vying for Jameson Taillon trade with Cubs

On its face, Taillon would be a competent and familiar pickup. From a value perspective, though ... the Yankees were unwilling to match Taillon's price on the open market last winter. Now, they'd suddenly be willing to absorb the pricey final two years of his contract ($18 million per season) without getting the benefit of his youngest year-and-a-half on the deal?

Adding a starter who's been worth 1.8 bWAR in 16 starts (7-4 record, 3.10 ERA) seems like solid insurance for the second half. Strictly from a value perspective, though, surrendering assets for only the back half of a deal you deemed too expensive in early 2023 is deeply silly (and so emblematic of the way the modern Yankees spend).

The Yankees could do worse than Taillon, and while they have bigger needs than the rotation at the moment, importing steadiness would be wise. The right-hander is also far from the worst Gerrit Cole Friend they could bring in down the stretch.

It should be noted, though, that Taillon has already suffered from recurring back issues this season. Just like the Scott Effross trade, "team control" might not be as valuable as the Yankees believe it to be. It's not ideal if the player is in the early stages of a lengthy breakdown, the cost of which you just opted to absorb.

Just something to be aware of as Cole likely counsels them to outbid Boston.