The Yankees and free agency, a look back

If anyone thought Derek Jeter was going to give an informative press conference about his contract situation, they must not have followed Jeter the last 15 years. Jeter says nothing about nothing and turns everything into a discussion about the team and winning.

There is very little doubt that Jeter will retire as a lifelong Yankee. But how will his contract situation be handled? Only time will tell, so until that news breaks, let's take a look back at how the Yankees and some of their top players of the past 30 years negotiated.

Andy Pettitte: What better way to start than one of the "Core Four." In January 2000, the Yankees signed Pettitte to an extension after going 14-11 in the 1999 season. The big lefty would remain with the Yanks until December 2003 when he signed a deal with the Astros. Pettitte felt slighted that offseason when the Yankees paid more attention to signing Gary Sheffield. Pettitte signed a 3-year, $31.5 million dollar contract and rejoined good buddy, Roger Clemens in his home state of Texas. Once that contract expired, he returned to the Yankees and he re-upped each year since.

Mariano Rivera: Another "Core Four" member never had an issue negotiating contract extensions with the Yankees. Rivera received extensions during spring training in 2001 and 2004. Rivera is the only player the Yankees have re-signed during spring training, as the Yanks stick by their firm rule of not negotiating extensions then.

Jorge Posada: The other "Core Four" member has agreed to contract extensions in January 2002 and November 2007. When Posada came to terms with the Yankees in 2007, he received a four-year deal worth $52 million. Posada was 35 at the time of the deal, still playing 140 plus games at catcher. Posada was injured for most of 2008 and only played in 111 games in 2009. The Yankees realized they gave Posada a ton of money on the back nine of his career to play a demanding position, similar conditions the Yankees will face when deciding on Jeter's contract.

Bernie Williams: After the Yankees' historic run in 1998, Williams became a free agent. in the prime of his career. Williams wanted his pay day and played hardball with the Yankees. He was an eye-blink away from playing for the Red Sox. Bernie resigned with the Yankees in November of 1998 to the largest contract given at that time in baseball: seven years for $87.5 million.

Alex Rodriguez: One of the more recent negotiations that was on the back pages every day. It's well documented that the Yankees would not budge on their offer after Rodriguez pulled out of his contract with the player option the Texas Rangers had given him. Things got so bad for A-Rod that he eventually fired super-agent Scott Boras and negotiated his own deal with the Yankees in December 2007. To date, it's the largest contract in all of sports: 10 years, $275 million. A-Rod didn't do too badly as his own agent.

Johnny Damon: The Yankees stuck by their initial offer of two years and $14 million. Damon, seeking two years and $20 million (at least) sat and waited as the market dried up quickly. Enjoy your stay in Mo-Town and the spacious Comerica Park at $8 million for one year.

Hideki Matsui: Yankee fans are still upset that the 2009 World Series MVP will not be back in pinstripes in 2010. The Yankees let him walk. If Yankee fans can get this upset over Matsui, they would tear down the new Yankee Stadium if Jeter ever went elsewhere.

And now, a more historical look at the Yankees and their free agents:

Reggie Jackson: Many compare Mr. October to Derek Jeter when it comes to clutch performances in the postseason, and the way these two figures became the face of the franchise in their respected eras. When Jackson’s contract was up after the 1981 season, the Yanks let him walk, and he signed with the Angels. In an interview on “Centerstage” a few years ago, George Steinbrenner admitted that it was a huge mistake to let a star such as Reggie Jackson leave the Bronx. We’ll see if the Steinbrenner family really learned its lesson. In all fairness, The Boss and Jackson had their ups and downs in the 1980s and much of that led Jackson to leaving the Yankees.

Willie Randolph: Randolph was a beloved Yankee who was an integral part of the Yankee championships in the late 1970s. He was such a cornerstone of the team that in 1986, along with Ron Guidry, Randolph was named co-captain. Then after the 1988 season, the Yankees turned around and signed Steve Sax to play second base.

Don Mattingly: Another Yankee captain that was the heart and soul of the team during the 1980s and early 1990s. Mattingly was seen early on as a bright budding star and the Yankees locked him up with a long contract to keep him out of free agency. There were always rumors that the Cardinals were interested in him and Donnie had a chance to go elsewhere and win. However, Donnie Baseball remained loyal to the Yankees.

Joe Torre: We can’t talk about contract negotiations and not mention Joe Torre. He may not be a player, but Torre is one of the main reasons the Yankees were so successful in his 12 years as manager. Following the 2007 season, Torre’s contract had expired and there were many rumors that the Yankees were ready to move on. However, the Yankees offered Torre a one-year deal worth $5 million and $3 million in incentives for every time the Yankees advanced in a round of the playoffs. Torre rejected the deal and cited the incentives as one of his main reason for not re-signing. Torre said in his press conference that he felt the Yankees gave him the money to motivate him. Torre also didn’t like the idea of coming back on a one-year deal and have his players deal with more questions about a lame-duck manager.

Many in the media speculated that the Yankees gave Torre a deal that they knew he would turn down. The only reasons the Yankees even offered him a deal was to save face with the fans. No one really knows, but it was by far the most public contract negotiations the Yankees have been involved in for quite some time.

Derek Jeter: Maybe the best litmus test to see how these impending negations will happen is to look back when Jeter was about to become a free agent. In 2000, the Yankees gave Jeter a one year deal worth $10 million before giving Jeter the ten-year deal worth $189 million. The talks were quick, smooth, and both parties walked away very pleased. One can argue that Jeter was in his prime and still had a lot to offer. Here’s the thing, Jeter delivered and now it’s time the Yankees reward him.