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The Deals NOT Made

This past summer Yankee General Manager Brian Cashman was under intense pressure to upgrade the Yankee rotation at the trade deadline, even if it meant reaching deep into farm system. The Yankee GM didn’t find a deal he liked, and stuck with the team as constituted at that point through the rest of the season. For those who felt he dropped the ball, they may want to take solace in the success of some deals that didn’t happen.

In 1992, the Yankees drafted high school shortstop Derek Jeter in the first round, sixth overall. After a rough start in his initial season at age 18, he worked his way through the Yankee system, attaining elite prospect status after a 1994 season win which he batted .344 over A, AA and AAA stops.

In 1995 he made his MLB debut, and played fifteen games. In 1995, the Yankee starting shortstop was Tony Fernandez. The three time all-star struggled at the plate, batting just .245, but had a long history of solid defense. With the hiring of longtime National Leaguer Joe Torre as manager prior to the 1996 season, the team was looking to put more emphasis on pitching and defense.

Defense was not considered a strength for Jeter. He made 29 errors at Columbus and in his breakout season of 1994 committed…56 errors.

The plan in Spring Training 1996 though was to give Jeter an opportunity to win the shortstop job, with Fernandez the safety net. Then suddenly Fernandez broke his elbow and Jeter was not enjoying a particularly good Grapefruit League season. There was considerable anxiety that the 21-year old wasn’t ready and his spring performance would carry over into the season. A backup plan was needed and Seattle called GM Bob Watson offering a solution – Felix Fermin. Fermin was a thirty-two year old .260 lifetime hitter who was at least an average defender at shortstop and second base. He was coming off of a .195 season in 1995 but batted .317 in 1994 for the Mariners.

The Mariners inquired about a couple of young pitchers – Mariano Rivera or Bob Wickman – in a deal for Fermin. Rivera had also made his MLB debut in 1995, and split time as a starter and a reliever, going 5-3 with an unremarkable 5.51 ERA. A tempting deal to make, and one that owner George Steinbrenner was considering heavily. Then assistant GM Brian Cashman recalled:

“It was a fight to convince The Boss to stand down and not force us to do a deal none of us were recommending,” Cashman said. “And it wasn’t because we knew what we had in Mo or Wickman, it was we had committed to go with young Jeter. Thankfully, we didn’t do that deal. That was as close as we ever came to trading Mariano.” As fans know, the deal was not made and Jeter and Rivera were major cogs in the 1996 World Series Champions. Jeter as AL Rookie of the Year, playing shortstop with a maturity and composure beyond his years. Rivera as half of a lethal bullpen combo with John Wetteland that basically shortened games to six innings.

Just think, Felix Fermin could have been both the trade bounty for Mariano Rivera and the one to block Derek Jeter in the lineup.

Interestingly, Fermin was released by Seattle in April 1996 and was signed by…the Yankees! He played seven games at AAA, then was released again on May 22, 1996. They must have felt they had something in Jeter, who at that point of the season was batting .265 and making the plays at shortstop.

That’s not the only deal the Yanks were glad they didn’t make. Andy Pettitte

Pettitte was another home grown Yankee who debuted in 1995. He finished third in 1995 AL Rookie of the Year Voting and second in 1996 AL Cy Young voting, and added his 1996 game five World Series pitching masterpiece to his resume. He averaged seventeen wins in the 1995-1998 seasons which saw the Yanks return to the postseason after a fourteen year absence and take two World Series titles. At age 26 in the beginning of the 1999 season he clearly looked to be a pillar for the Yankee staff, primed to become one of the great pitchers in franchise history.

Then the tall lefty struggled in 1999 though and was 7-8, 5.65 as of July 28th, and with the trading deadline just three days away Steinbrenner entertained offers. He had a deal on the table from Philadelphia for three minor leaguers –Adam Eaton, who went on to a 4.94 ERA over a ten-year career, Reggie Taylor, a minor leaguer who later batted .231 over five seasons with three teams and pitcher Anthony Shumaker, who went on to appear in eight career games. Thankfully Torre, now GM Cashman and pitching coach Mel Stottlemyre talked the Boss out of making the deal.

Pettitte righted himself and went 7-3, 3.46 the rest of the way, and won two postseason games. He averaged seventeen wins annually from 2000-2003, and was inexplicably allowed to leave as a free agent after winning 21 games in 2003. After three years in Houston, he came back to the fold in 2007 and finished his career with 256 wins, 219 of them in Pinstripes.

Bernie Williams

In the mid-1990s Bernie Williams looked to be slowly growing into the regular centerfield job for the Yankees. There were growing pains through the process, and his steady improvement didn’t satisfy Steinbrenner, as the soft spoken switch hitter was rumored to be dealt to Montreal for Larry Walker in 1993, and to San Francisco for Darren Lewis in 1995.

Despite establishing himself as an elite player in 1996 and 1997, the rumors continued, and after the 1997 season there were rumors of Bernie heading to Detroit for young pitchers Mike Drumright and Roberto Duran, who went on to combine for no MLB victories over their careers, and to Chicago Cubs for Lance Johnson.

Steinbrenner seemed to finally take to Williams after his .997 OPS, Gold Glove season in 1998, and a personal appeal made by Williams to be a long tenured Yankee. The Yankee owner signed the outfielder to a 7 year, $87.5-million dollar deal which kept him in pinstripes the remainder of his fine career.


It will be interesting to watch the intrigue of the upcoming off-season and determine who will – or will not – be the Yankees to be dealt. The names being floated like Andujar, Frazier, Garcia all look to have high ceilings, and be major leaguers for years to come. One thing we’ve discovered the past few years is that Cashman will not rush into deals for short term fixes. With the Yankees’ young core primed to produce tangible results, deals made to compliment the core gain increased importance and scrutiny. The stakes are high, be it in those acquired, or those dealt.

Perhaps he has learned some lessons from the past.


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