Cody Ross  counts outfielder Josh Willingham  as one of his closest friends in baseball. Both achieved status as big league regulars with the Marlins in 2006, when Willingham made a splash as a 27-year-old rookie who swatted 26 homers and Ross finally getting a big league opportunity with a Marlins team that acquired him for $1 from the Reds, hitting 11 homers in 91 games with Florida while showing the ability to play all three outfield positions.
The two outfielders spent three years together with the Marlins, but after the 2008 season, he was dealt to the Nationals, spending a couple years in Washington before going to Oakland in 2011. Ross, meanwhile, remained with the Marlins until 2010 before he was sent on a waiver claim to the Giants  for the stretch run that yielded an unforgettable October. He remained in San Francisco for 2011, living near his former Marlins teammate.
But after the 2011 season, both Ross and Willingham found themselves on the same team — which is to say, none at all. The two were free agents, albeit ones in strikingly different boats.
Willingham had a strong walk year with the A’s, smashing 29 homers and driving in 98 while hitting .246/.332/.477/.810 in 136 games as a 32-year-old. Ross, as a 30-year-old, put up far more modest totals, hitting .240/.325/.405/.730 with 14 homers in 121 games for the Giants in 2011.
While the two expected to receive calls from similar sets of teams — chiefly, those in the market for right-handed-hitting outfielders with power — Ross also understood that he would be in line for a different sort of deal than his friend.
“I was talking to him throughout the offseason, seeing who was interested and who wasn’t, just kind of bouncing stuff off of each other,” Ross said during the season. “He had a little better season than I did last year, and got paid — rightfully so. I knew he was going to be one of the guys to set the market as far as power-hitting right-handers. Obviously I couldn’t compare myself to him, but I was so happy for him to be able to get his deal.”
Willingham received a three-year, $21 million free agent deal from the Twins. Ross, meanwhile, took a one-year, $3 million deal with the Red Sox , opting to pass on two-year offers that would have given him more than $3 million per year (but less than $5 million per year) in hopes of going to a favorable hitting environment (a departure from Florida and San Francisco, both of whom play in parks and divisions that tend to be hostile to big power numbers) where he could boost his numbers in anticipation of another run at free agency following the 2012 season.
The strategy paid off, as Ross slammed 22 homers in 130 games while hitting .267 with a .326 OBP, .481 slugging mark and .807 OPS, with his OBP and OPS both ranking as career-best marks for any season in which he had at least 200 plate appearances. That line closely resembled the one that Willingham delivered with the A’s (albeit in more challenging hitting environment) prior to getting his three-year deal from Minnesota.
“I felt like this was a perfect spot for me to get my value back up and basically I rolled the dice on a one-year deal,” Ross said of Boston. “Hopefully it pays off.”
It seems extremely likely that Ross will secure a multi-year deal, though it remains to be seen whether it’s with the Red Sox.
Sox GM Ben Cherington said on the final day of the regular season that the team had talked with Ross about the team’s potential interest in retaining the outfielder.
“Cody fit in well and had a good year,” said Cherington. “[Outfield] is an area of need going forward.”
John Farrell  likewise said that he’d exchanged texts with the free agent by the time of his introduction as Red Sox manager last week. Still, with the exclusive window for teams to negotiate with their own free agents closing just after midnight on Saturday, it seems likely that Ross will explore his market value, with the Sox more inclined to keep the door open to the outfielder rather than rushing to lock him up before he can talk to other clubs.
Where does that leave Ross? It remains to be seen.
But it’s worth noting that the Sox are focused on disciplined spending in the very mold that netted them Ross last offseason — chiefly, waiting out the top-of-the-market signings and then waiting for players who are open to short-term deals and who represent promising fits for their ballpark and team. If the team opts to go that route, looking for buy-low candidates such as Ross and Adrian Beltre , then the likelihood of retaining Ross once he starts talking to other clubs seems likely to diminish.