Following the 2009 season, there was much speculation whether the Red Sox would attempt to re-sign Jason Bay or if they’d go for an even bigger fish and try to sign Matt Holliday in free agency.
As it turned out, they did neither. With both Bay and Holliday still waiting around for bigger offers to come in, the Red Sox spent $82.5 million to sign John Lackey and then chose Mike Cameron to round out their outfield. A year later, they signed Carl Crawford to a $142 million deal to take over as their long-term left fielder.
The Red Sox did offer Holliday $85 million for five years, though. And he was interested in playing in Boston.
“I liked playing there in the (2007) World Series,” he told the Boston Herald. “They were a team I was interested in. I knew some people in the organization and they were obviously very competitive, with a chance to win the World Series every year. They had everything I was looking for. And so did St. Louis – but I was definitely considering Boston if they had stayed in it.”
Of course, Holliday eventually re-signed with the Cardinals for $120 million over seven years, and he seems to have no regrets.