"The Red Sox had a prime free agent target in the winter of 2009, and it wasn't Jason Bay or John Lackey.

It was Matt Holliday.

They didn't get their man. The Cardinals outbid them by nearly $40 million.

But it's nevertheless a fun parlor game to wonder how different the 2011 Red Sox would look with Holliday in left field instead of Carl Crawford and Lackey pitching God-knows-where instead of here.

Because had the Sox signed Holliday, they almost certainly would not have signed Lackey that same winter. And a year later, they'd have had no room for Crawford, who ended up signing for seven years and $142 million.

The Red Sox' interest in Holliday was real, and it was mutual.

"I thought there was a chance," Holliday said at the All-Star Game. "Going in, I didn't know what to expect, but I thought there was a chance."

Holliday had a number of criteria. He wanted to play in a market where baseball mattered, the team competed, and the World Series was a realistic annual goal. "The Red Sox had all of that," he said.

While Bay was believed to be the team's No. 1 priority, the reality was those negotiations had collapsed the previous summer over concerns about his health. When free agency began, the four-year, $60 million deal Bay was supposedly leaving on the table had actually already been yanked off it, replaced by a lesser one.

The Sox had no such trepidation about Holliday. They offered him a five-year, $85 million deal early in free agency. His agent, Scott Boras, countered at a number roughly double that."