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Remembering the Red Sox’ pursuit of Andy Pettitte 02.04.11 at 6:11 pm ET
By Alex Speier

The Red Sox made an aggressive offer to then-free-agent Andy Pettitte in 2003. (AP)

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, Print  |  Email  |  Bark It Up!  |  Digg It
  • bosoxyaz8

    2003-2004 just a mindblowing period in sox yanks history. the greatest two years ever in baseball history.

  • Steve

    Thanks Alex for the reminder of the Sox attempt to lure Andy which would have made for some remarkable news! Can’t imagine though, no Thanksgiving trip to the Shillings, no bloody sock, etc.

    Have to respect Andy Pettitte.

  • dano_in_ny

    You’ve got to finish the thought. If Pettitte was signed, then Schilling likely wouldn’t have been. If Pettitte got hurt in 2004, then we likely wouldn’t have made it back, which took all of Schilling’s ability and guile in the postseason, along with the bloody sock. And we wouldn’t have gotten the monkey off our back, but we would have had Pettitte as a no.2 to no.4 starter and we might have made the postseason in a few more years, which ones? when Schilling was hurt or gone.

  • babe ruth

    Just think about it Pettittle won more championships in his career then the whole Sox franchise in 100 years.

  • Steve

    A classier guy than Johnny Damon.

    Who leaves every team on bad terms, but is now on his “dream team,” the Rays.

    You go, Johnny.

  • SoxOrGoHoMe

    Actually that’s not true, Babe Ruth. 100 years ago would be 1911, right? Okay. The Philadelphia Athletics won the world series in 1911, exactly 100 years ago. Then in 1912, the Red Sox won it all. They won the world series again in 1915 and 1916. Then in 1918, their last year with Babe Ruth, they won the series for the final time that millenium. In 2004, the Sox had the biggest comeback in sports history and beat the hated yankees. They won it all again in 2007. Thats 1912,1915,1916,1918,2004, and 2007. Just in case you can’t count, that’s six championships in the past hundred years. Pettitte has won 5 in his career.

  • babe ruth

    I stand corrected, thanks!! There is one thing i am sure of, New York Yankees team of the century

  • Robert

    How could he have turned down 52 million from the Sox, and the signed in Houston for 31 million. Had he signed with the Sox,they may have won all three trophys from 05 to 07. After, 04 Schilling was pretty much done.Alex,you might want to recall the lousy stunt that Bernie Williams pulled on the Red Sox when he used them to up NY’s offer. Now, that would have altered history.They had a chance to alter history this winter by signing Rivera and Jeter.

  • Robert

    Does the 2000 WS victory by the Yankees over the Mets count as this century or last? If it counts for this century,the Sox and NY are even.

  • Matt

    C – Jason Varitek
    1B – Mark Teixeira
    2B – Dustin Pedroia
    3B – Mike Lowell
    SS – Derek Jeter
    LF – Johnny Damon
    CF – Bernie Williams
    RF – Trot Nixon
    SP – Curt Schilling
    SP – Andy Pettitte
    SP – Mike Mussina
    RP – Mariano Rivera

    That’s my all-Sox/Yanks NICE GUYS team in recent years…hopefully I’m not forgetting anybody…

  • Robert

    If you are a Red Sox fan, Bernie Williams was a hated Yankee.He used the Red Sox to get more money from NY.He had that obnoxious pop up slide,as he always seemed to be crossing the plate.He killed the Sox on the field.He was also one of the most underated players of all time.There wasn’t anything he couldn’t do.He should go to the Hall but his numbers won’t support it.If anyone was a pillar to those great 90′s team’s,it was he.I can’t think of any Yankee that’s is a nice guy. To want to play for a team and a city that has won so much is a front runner.So many of them want to play there,it is sickening.(Hello Sabathia and Tex)Cliff Lee told them to stick it and went to the Phillies.Way to go, Cliff!

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  • Randy Stream

    Glad they didn’t suspend him because then he would’ve missed Tuesday night’s rematch.

  • paul

    not a surprise

  • Brad

    I hope Shanahan goes missing.

  • http://twitter.com/jetsjets1028 joe lepianka

    wow shanahan is joke if it was a bruins player deff wouldve been suspended what joke shanahan biasness

  • Nitetrain

    Should have gotten 1 or 2 games. Having said that, I am thrilled he’ll be in uniform on Tuesday in Boston.

  • Misc22

    I’m from Boston, but this hit wasn’t worthy of suspension, he came around to the side/front before he laid the hit on him, and if you didn’t listen to Jackass Edwards (sry but hes an idiot), you wouldn’t think it’s as bad. Jack made it sound like he was going 100 MPH and jumped 5 ft in the air and hit him with a hammer in the head…penalty…sure, suspension? Nah….and come on…you can’t tell me that Lucic hit on Miller was unintentional? 

  • Smac3407

    You leave your feet, you get suspended. Consistent application of the rules please. However, Lucic will handle the discipline on Tuesday night…

  • Cory Ducey

    I’m sorry.  But he clearly stated that if primary contact is to the head, there will be supplementary discipline.   There was contact to the head and it was blind side.

    No consistency…

  • http://pulse.yahoo.com/_RQDEFBPO2D4T3KVBEFNLQUDPFY Peter

    Give Shanahan credit, he and the disciplinary office are consistent when it comes to reviewing hits against any Bruin player. Still waiting for someone to get suspended for a hit to the head on a Bruin. 

  • Risingart13

    Sure! I bet if it was Lucic hitting Turris he would of been suspended. I don’t know who’s worse this year the Hockey League Operations or the f***’n officiating! Another blown call, thanks Shamaham you jerk!!

  • Gman

    Sorry, Thorny will beat Lucic to Turris.

  • Mike66r

    Once again the league falls down and as always the Bruins will settle this issue for themselves.
    Tuesday will be a war.
    Good luck Turris. ha ha ha ha ha

  • Christophermehegan

     good point there i wanna see turris in a tussle with shawn thornton betch ya who wins that bout

  • Josh4390

    If the primary contact is the head…..then suspension!  How bout a fine!!!!  Something.  Isn’t that what we have been led to believe.  Regardless of the intent.  He should have gotten at least a game or two.  The hit was not quite the ”crime”  that Edwards portrayed, but still a punishable offense. 

    This years Horton hit (how does a guy get a possible season ending concussion in open ice without contact to the head?) and in the same game Kelly took a hit in front of his own net to the side of the head and no call or conference from the officials or the league.

    No consistency Shanahan!!!!!  None.

  • Alexander Ienzi

    what a joke…

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