When the Yankees almost traded Andy Pettitte

Analyzing Tim Lincecum's mechanics
Avert your eyes! Another Santana update

Two weeks ago, I had fun with a little What If? scenario involving Randy Johnson in 1998. This time, at the suggestion of Hollaforskolla, I’m jumping ahead a year to the 1999 trade deadline when Andy Pettitte was nearly traded.

It is the morning of July 30, 1999, and the Yankees are right where they should be. At 61-39, the defending World Series champions are in first place with a 6.5 game lead over the Red Sox. But all is not well in Yankeeland.

Andy Pettitte, 27 and not too far away from free agency, is struggling. Two days before, Pettitte couldn’t get out of the 4th inning against a pathetic White Sox team, and the lefty finds himself 7-8 with a 5.65 ERA. The Yanks are on the hook in 1999 for $5.95 million and are facing another year of arbitration before free agency. While to us in 2008, that seems like small beans, to George Steinbrenner in 1999, Pettitte is not coming through and the Boss has made it known that Andy Pettitte is on the trading block.

The next four days bring a whirlwind of rumors and near-trades. The stories provide us with a glimpse into what could have been a very costly move. On July 30, Buster Olney, then the Yankee beat writer for The Times writes that Steinbrenner “did not order that Pettitte be traded, but the actions of his subordinates in the hours after the staff meeting in Tampa, Fla., suggested that they were working hard to formulate an acceptable deal before the deadline Saturday night.”

That day, the Yankees are rumored to be in discussions with the Phillies. A potential deal with net the Philadelphia Phillies Andy Pettitte, and the Yanks would get Adam Eaton, Anthony Shumaker and Reggie Taylor. At the time, those were three highly touted prospects. It’s funny how things work out.

Also on the table is a deal with the Giants for Shawn Estes. Olney, proving that old habits never ever die, does indeed call Estes “a better fit” for the Yankees because he’s due just $2.15 million in 2000. Imagine Andy Pettitte’s almost getting traded because of a $4 million difference.

As the clock ticks down to midnight on July 31, 1999, Pettitte’s future in pinstripes looks dim. As Olney notes, on the same day they reacquired Jim Leyrtiz, the Yanks had a deal in place with the Philadelphia Phillies. This deal however is contingent upon another deal: If the Yanks can land Arthur Rhodes or Roberto Hernandez, Pettitte is gone.

There are a few hitches. To get Rhodes, the Yanks would have to send D’Angelo Jimenez and Luis De Los Santos to the Orioles. At the time, Jimenez was a highly-regarded prospect. A terrible motorcycle accident would change his career a few years later. To give up Hernandez, the Devil Rays wanted one of two young kids: Alfonso Soriano or Nick Johnson.

Well, as we know, nothing happened, and the fallout exposed some divisions in the Yankee organization. George Steinbrenner, for one, was less than enthusiastic that Joe Torre intervened to keep Andy Pettitte. ‘Our manager seems to think things are all right,” Steinbrenner said. ”I have great confidence in my manager.”

Pettitte wasn’t too enthused by that statement, according to Olney. ”You want your owner to want you around,” he said.

The next day, George backtracked a little. ‘The manager is happy,” he said. ”That’s good by me.”

But when all was said and done, Andy Pettitte came oh so close to getting traded on that fateful night in July. But he wasn’t traded, and he responded in kind. Through August and September, Pettitte would go 7-3 with a 3.46 ERA, and he threw two stellar starts in the ALDS and ALCS before getting bounced early in game 3 of the World Series. The Yanks would eventually win that game on a home run by Chad Curtis in the 10th.

We know what happened after 1999 with Andy Pettitte. He had some stellar seasons in the Bronx, and except for a terrible start in the 2001 World Series, he pitched his heart out in the postseason. His game 6 start in the 2003 World Series against the Marlins was brilliant even though he was overshadowed by Josh Beckett.

This is one trade that the Yanks are glad they never made. Andy Pettitte has been far superior than Adam Eaton, and the money stopped being an issue for the Yanks shortly after they won again in 1999 and 2000. But eight years ago, without hourly-updated blogs and the constant surveillance of the Internet, not too many people knew that Andy Pettitte came to within a hair’s breadth of being traded. In the end, Pettitte and the Yanks were, to borrow a phrase, a good fit.

Analyzing Tim Lincecum's mechanics
Avert your eyes! Another Santana update
  • Phil McCracken

    Good read Ben. I had almost forgot about those potential Pettitte trades. I remember I liked Estes back then.

    Not even Joe Torre could stop Steinbrenner when he let Pettitte walk as a free agent after the 2003 Series. Even though Cashman had wanted Pettitte to return. While the Yankees did eventually put up an offer, their failure to show enthusiasm is what let Pettitte to Houston. Pettitte walked, we got a walking timebomb in Kevin Brown, and a first round pick from Houston.

    If anyone should be getting credit for landing Phil Hughes, it should be Steinbrenner.

  • Deezer

    GREAT feature. I want more.

  • Geno

    Does this look back make a case for getting Santana? It seems like every prospect involved in that whole deal didn’t work out. The only one who did work out was the established commodity – Pettite.

    That being said, I still want to see the young guys develop in pinstripes.

  • huuz

    did any of the phillies prospects have any MLB experience, or were they still in the minors at the time of the trade? our “big 3” have *some* MLB experience to back up their great minor league numbers.

    Geno has a valid point. we all *love* our prospects, but so few of them make it that getting the known commodity while their value is high is also good business.

    i’m not even sure how i feel about trading hughes + others for santana, but it is a difficult call.

    • http://www.riveraveblues.com Ben K.

      It’s impossible to compare Adam Eaton to Phil Hughes or Ian Kennedy. Eaton’s MiLB numbers and his prospect profile were miles worse than Hughes’ and Kennedy’s. Not even close.

  • huuz

    wow, you’re right. i just checked Adam Eaton, Anthony Shumaker and Reggie Taylor on baseball-ref and looked at their numbers from the minors. none of these guys were any good. eaton never had more than 1K/IP, gave up lots of hits and had average control. shumaker got worse as he went from A to AA, and got worse by repeating AA. and taylor was just garbage. an outfielder whose minor league OPS barely cracked 0.700…ouch.

  • Joel

    At least Hank has the hot’s for one of the best lefties in baseball. That Eaton, Shumaker & Taylor deal would have been a disaster. There’s not one blue chipper in the bunch.

  • steve (different one)

    crap like this is why it is so hard to evaluate Cashman’s tenure before 2005. how do you make a good trade when your owner orders you to trade someone while their value is at its absolute lowest??

    don’t think Pettitte didn’t remember this incident when he left in 2003. the fact that Cashman was able to lure him back in 2007 indicated to me that a lot of Pettitte’s problems were with Steinbrenner.

  • Joel

    Till this day Cashman takes the public hit for Wright when I remember him on the radio saying he had no idea the Yankees signed him.

    Wells round 2, Giambi (Cash wanted Tino back), Wright, Womack, Mondasi, Lofton, Sheffield (Cash wanted Vlad), Brown (Cash wanted Pettitte back)

    ^^^^ thank god the old man is retired!

    • Kyle

      I thought I remembered reading that the Yankees had all but signed Vlad until Big George signed Sheff on his own?

    • http://www.riveraveblues.com Joseph P.

      Ah, but to play the hindsight card on you, if the Yanks kept Pettitte, there would be no Hughes.

    • DCR

      I don’t mind Giambi over Tino.

    • davon

      that would of been crazy vlad in a new york uniform just imagine the yanks lineup right now a rod jeter VLAD TEIXEIRA cano it would of been crazy but no steinbrenner had to mess things up sheffield did do gud but vlad??? i pick vlad over sheffield anyday

  • AndrewYF

    Of course, things could have been very different in 2005 and 2006. Not 2004, because Pettitte had his surgery that year.

    • YankeeJosh

      Who knows. Pettitte’s elbow finally gave out on a check swing in 2004. He wouldn’t have been batting with the Yanks. Maybe he survives the year and leads the Yankees to victory. Maybe he defers surgery until 2005. It’s really hard to say. Either way, I’d have felt better with an injured Pettitte starting as opposed to a healthy Kevin Brown.

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  • DCR

    I still think that Pettitte is pitching hurt. He will benefit a lot from the ASB and I expect him to have a good second half.

  • http://youcantpredictbaseball.wordpress.com/ bexarama

    Thank you God this did not happen.

    /mega late reply’d

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