And, within the internal discussions in New York's front office, the Yankees appeared on the verge Friday night of making an offer to the Twins that included Hughes.
"If they put Hughes in the deal," said one person familiar with the talks, "that could get it done for Minnesota."
Even if the Yankees and Twins build a framework for a Santana deal around Hughes, center fielder Melky Cabrera and another top minor league prospect, this would be only the first step toward completing the trade. Because Santana has a full no-trade clause, the Yankees may have to offer the two-time Cy Young Award winner a record-setting deal of something in the range of $25 million a year for six years.
No pitcher has ever received a multiyear deal for more than $20 million.
Up until now, sources say the Yankees have been willing to talk about pitcher Ian Kennedy, Cabrera and others, but not top pitching prospects Joba Chamberlain and Hughes and second baseman Robinson Cano. The Red Sox have talked about a willingness to offer pitcher Jon Lester, center fielder Coco Crisp, minor league infielder Jed Lowrie and a minor league pitcher -- but Boston doesn't want to surrender center fielder Jacoby Ellsbury or pitcher Clay Buchholz.
But there is more pressure on the Yankees to acquire Santana or another veteran pitcher, because the projected Yankees' rotation, as of today, lacks experience, and because friends of left-hander Andy Pettitte believe there is a real chance that he is going to retire. The Yankees may not learn until late December or January about what Pettitte's plans are for 2008.
Those considerations may nudge the Yankees into adding Hughes to their offer for Santana.
The Yankees and Red Sox are also engaged in ongoing talks with the Oakland Athletics about Dan Haren, an accomplished pitcher who is a much cheaper option than Santana. Haren would cost, in prospects, a package comparable to what Santana is commanding, but he is already under contract for the next three years at $16.25 million (presuming his team exercises an option for 2010).
Buster Olney is a senior writer for ESPN The Magazine. Information from ESPN.com senior writer Jayson Stark was included in this report.