To no one's surprise, Holliday's agent believes there is no comparison.
Scott Boras, bringing a mid-afternoon buzz to the Indianapolis Marriott lobby before the announcement of the big Detroit-Arizona-Yankees trade, told reporters that Bay's negotiations have no bearing on Holliday's pursuit of a new home, because Holliday is so much more versatile and well-rounded a player.
"They're different players for me," Boras told reporters. "Matt is a very athletic player. He's a complete player. Certainly Jason Bay is a very fine hitter. But Matt Holliday is a great baserunner. He's really athletic. He could have played in the NFL. He's that kind of guy.
"He has the type of power with a line-drive swing that allows you to play in bigger ballparks and still produce 100 RBIs and 100 runs scored. He is, to me, more capable of delivering the production in a wider variety of ballparks."
With trade talks and this weekend's non-tender deadline making for slow going for free agents, it's likely that the Holliday and Bay negotiations will drag on a while. In an ESPN.com poll earlier this winter, 11 of 20 executives surveyed said they preferred Holliday to Bay, but both players have their supporters.
Holliday, 29, is a three-time All-Star and the 2007 National League MVP runner-up. He declined a football and baseball scholarship to Oklahoma State to sign with Colorado in the 1998 draft. Bay, also a three-time All-Star, posted his fourth career 30-homer, 100-RBI season this year in Boston.
The Cardinals, Red Sox, Mets, Giants, Mariners and Angels are among the teams believed to have a potential interest in Holliday or Bay, depending on how events unfold.
Boras touched on Holliday's situation from several angles during a 35-minute give-and-take with reporters. He compared Holliday's production to Mark Teixeira's (but declined to say if that equates to a $180 million, Teixeira-type contract). He suggested the Cardinals could make it more enticing for Albert Pujols to stay in St. Louis by keeping Holliday and strengthening their lineup. And he stressed that Holliday's suitors have just as much input in the timetable as he does.
"The time frame of these things is predicated more on the clubs," Boras said. "I don't write checks. I can go in and talk about a lot of things, but I don't make that decision."
Boras contends that Damon's ability to get on base and hit second in the order still make him a valuable commodity in left field for the Yankees. Although Granderson hit 30 homers this season in Detroit, he struck out 141 times and posted an on base percentage of .327. Damon had a .365 OBP hitting in the No. 2 spot behind Derek Jeter.
Indications are that New York is interested in bringing back Damon, but short-term and not for the longer, three- or four-year deal that Damon wants.
New York general manager Brian Cashman said Wednesday that Granderson's array of attributes made him particularly attractive to the Yankees with Damon and Hideki Matsui both possibilities to leave through free agency.
"This gives us a comfort level in knowing we have such an important piece of our lineup taken care of," Cashman said, "but the next few decisions we have are just as important. We're continuing to try and reshape this thing moving forward."
Jerry Crasnick is a senior baseball writer for ESPN.com