Henderson signed as a free agent with the Red Sox in 2002 and became the oldest player to play center field in major league history with them. At age 43, he played in just over 70 games and still managed to hit 5 home runs and steal 6 bases. Henderson's arrival in Boston marked a curious statistical oddity. From his 1979 debut through the end of the 2001 season, he had stolen more bases by himself than everyone who had ever played for the Red Sox combined: 1,395 steals for Henderson, 1,382 for the Boston franchise. The Red Sox finally "passed" Henderson on April 30, 2002. While statistically, Henderson certainly didn't have a huge impact on the Red Sox, his signing marks the beginning of a critical philosophical shift in the organization. Prior to Henderson, the Red Sox were always built as a slugging team. Sure there were guys like Ellis Burks who came along every now and then who could steal a base or two, but the Sox were never built as a team who could take the extra base on a single (and we Red Sox fans now know how important that can be following Dave Robert's steal in game 4 of the 2004 ALCS). They were always built to put men on base and either score them via a home run or leave them stranded. Henderson was the first step in an evolution that is still on-going with the 2009 team.
Here’s an anecdote I found about Rickey’s time with the Red Sox over on Buckey Planet:
“Henderson signed a minor league deal last year with the Boston Red Sox that included an invitation to spring training and a $ 350,000 salary if he made the team. After he played his way onto the Boston roster with an impressive spring, Henderson groused that the Red Sox were underpaying him.
Interim general manager Mike Port reminded Henderson of the conditions he had agreed to.
"Oh, that?" Henderson replied. "I canceled that contract."
Says Port, "It was the first and only time I've ever had a player tell me he canceled his contract."
Red Sox president Larry Lucchino telephoned San Diego G.M. Kevin Towers, asking how Towers had appeased Henderson during their contract squabbles in the past. "I was on the golf course late in spring training one year when Rickey called to close a deal," Towers says. "I was putting, and my wife took the call. I said to her, 'Ask him what he wants.' She said, 'He wants a living allowance.' And I did it. That's how we closed the deal."Lucchino liked that idea. The Red Sox agreed to pick up the tab on the suite Henderson was renting at the Boston Ritz-Carlton, which ran $ 10,000 a month.”