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Remembering the Red Sox’ pursuit of Andy Pettitte

02.04.11 at 6:11 pm ET

It was an offer that could have changed history.

It was weeks removed from the 2003 postseason, and the Red Sox were trying to recover from the crushing end of their 2003 season. That the Yankees had lost to the Marlins in the World Series was little consolation to a Sox team that had come within five agonizing outs of finally escaping the yoke of their divisional oppressors, only to suffer an infamous defeat in Game 7 of the ALCS that would soon lead to the firing of Grady Little and an effort to bolster the Sox roster for the following year.

Andy Pettitte had played a part in the Sox’ demise that postseason. The left-hander, as part of a spectacular postseason in which he went 3-1 with a 2.10 ERA in five starts, had shut down the Sox in Game 2 of the ALCS, helping to restore order for the Yankees after the Sox had won Game 1. Though Pettitte claimed a no-decision in Game 6 of the series (a Sox win), the 31-year-old had established himself as one of the most important members of the Yankees, and one of the best southpaws in the game.

Pettitte was a free agent at an opportune moment. He had gone 21-8, made all his starts (33), achieved a 4.08 ERA while punching out a career-high 180 and finished sixth in the AL Cy Young race. The Yankees wanted to retain him, but the Red Sox were desperate to find a front-of-the-rotation complement to help them make a run at the Yankees.

And so, recalled one multiple sources involved in Red Sox decision-making at the time, as soon as the free agency period began and teams were allowed to make offers to other teams’ free agents, the Sox came in with an immediate offer for Pettitte. The offer was for four years, $52 million.

Though their interest was genuine, the Red Sox were anything but confident in their chances of signing the left-hander. They had every expectation that he would either re-sign with the Yankees or join the Astros in order to pitch close to home. Realistically, the Sox were hopeful that a significant offer might help push the left-hander away from the Yankees (or at least make the cost of retaining him even greater).

Pettitte, in a 2007 interview, said that he never seriously considered joining the Sox.

“I couldn’t see myself competing against the Yankees as a [member of the] Red Sox,” Pettitte told the Hartford Courant in 2007. “They made a great offer. I love their franchise. They have a great organization. But with the friendships I’d built up [in New York], I couldn’t see myself doing that.”

He took little time to turn down the Sox’ offer, and the Sox moved on almost immediately. But, whether influenced by the disparity between the Sox’ and Yankees’ offers or not, Pettitte did end up leaving New York that offseason. He signed a three-year, $31.5 million deal to pitch for the Houston Astros and live in his Deer Park, Tex., home; the Yankees, according to reports at the time, made a final offer of three years, $39 million.

That left both the Sox and Yankees to address holes in their rotation. The Sox made their deal for Curt Schilling — described as the Sox’ “most serious and purposeful” pursuit of that winter — later in November, while the Yankees agreed to a deal with the Dodgers to acquire right-hander Kevin Brown.

All of that makes for a couple of fascinating hypotheticals: How would history have been different had Pettitte switched allegiances and joined the Red Sox? Alternately, how might the rivalry’s script be different had Pettitte not left New York after 2003?

Obviously, no one can answer those questions. But Pettitte’s subsequent performance against the Sox when he returned to the Yankees following the 2006 season makes the subject no less interesting to contemplate. In his second tour with the Yankees, his team went 10-6 in the pitcher’s remaining 16 career starts against the Sox. Pettitte retires as not just one of the winningest Yankees of all time but also one of the most successful pitchers of all time against the Sox, having gone 18-10 with a 3.91 ERA in 39 career appearances (37 starts) against Boston.

In fairness, Pettitte’s numbers against Boston during that time were more modest: He went 5-5 with a 5.38 ERA over the past four years against the Sox. Moreover, Pettitte was limited by injuries in his first season with the Astros, making his last start in August and missing the 2004 postseason. He came back with tremendous seasons in both 2005 and 2006 for the Astros before returning to New York as a free agent for the last four years of his career, but if Pettitte hadn’t been healthy in 2004, then he would have been able to do little to help the Yankees withstand the Sox in their historic ALCS comeback en route to Boston’s first World Series in 86 years.

Still, while the Sox’ offer to him after the 2003 season is nothing more than a footnote in the left-hander’s career, it conjures a fascinating exercise in revisionist history.

Read More: Andy Pettitte, Curt Schilling, kevin brown,
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