Like most memories first forged in our younger years, baseball is easily romanticized. Chances are you hold a soft spot in your heart for your first baseball hero or favorite team with much the same fondness you have for your first car, first love, first… Well, you get the idea. Colin Wyers recently described the hero-worship phenomenon beautifully here.

For many of the greatest players or teams, there is a moment. An achievement. A record. A championship. A play. Bill Mazeroski, 1960. Perfection from Sandy Koufax (45 years ago Wednesday). The Idiots of 2004. Willie Mays, 1954. It’s at those moments—now frozen in time—when fans yield a part of themselves to those players forever.

So it’s probably inevitable that fans feel hurt—betrayed, even—when a player lobbies for more money or seeks to leave one city in favor of another.

In announcing his retirement in 1993, Hall of Fame third baseman George Brett said, "I could have played another year, but I would have been playing for the money, and baseball deserves better than that.”

Though no one doubts Brett’s love of the game, he did, in fact, earn a salary, like every other player. And his contract status, like that of every other player, was an issue throughout his career.

Brett’s contract paid him a $1.5 million salary for 1991, plus another $450,000 or so from a real-estate investment through Royals co-owner Avron Fogelman. After several players signed contracts paying salaries between $3 million-$3.75 million in the winter of 1991, Brett—the reigning American League batting champion— sought to renegotiate his deal, despite the fact that it had one year remaining, with the Royals holding options for 1992 and 1993.

The Royals considered their options and decided they had little choice but to re-work the contract of the franchise icon closing in on the 3,000-hit milestone. The following spring, Brett signed a new deal worth $7.7 million for the 1991 and 1992 seasons, with an option for 1993.

And Brett is one of the handful of free agent-era players who spent his entire career with one club and—at least in theory—had an easy go of it when it came to the sometimes cruel business side of the game. Brett never seriously entertained thoughts of leaving, and the Royals never reached the point they wanted to be rid of him. But even for that rare group of players, the business side of the game intervenes. As Ben Lindbergh chronicled last week, the Yankees will face a similar situation with Derek Jeter this winter.

Two long-time Chicago icons recently served as reminders that when a prominent player does leave, the fallout can last for years. As the White Sox retired the jersey No. 35 of prodigal slugger Frank Thomas, former Cubs star Sammy Sosa lobbied the North Siders for the same honor. The Chicago tenures of each player included contract disputes and ultimately ended with awkward departures.

The White Sox invoked a “diminished skills” clause in Thomas’ contract after the Big Hurt had slumped to a .252/.361/.472 slash line as a 34-year-old in 2002. The clause—euphemistically known as “revised payment rights”—allowed the White Sox to defer more than $10 million of Thomas’ $10.3 million salary if he did not make the All-Star team, win a Silver Slugger award, or rank in the top 10 of the 2002 MVP balloting. Thomas responded by exercising his right to file for free agency before agreeing to a reworked contract with the White Sox for 2003-05.

The White Sox had persuaded Thomas to agree to the “diminished skills” provision after Michael Jordan had a similar one included in one of his contracts with the NBA’s Bulls, another of the Chicago properties of Sox owner Jerry Reinsdorf.

But the “diminished skills” episode was not the last contract squabble of Thomas’ career. In the afterglow of the White Sox' 2005 world championship, Thomas exercised his $10 million player option to return for 2006. The club, however, chose to decline the option and instead acquired Jim Thome in a trade—a decision that did not sit well with Thomas, who felt slighted that Reinsdorf had not called to tell him of the team’s plan to move in another direction. After a year with Oakland, Thomas signed a two-year free-agent deal with Toronto. However, the Blue Jays released him just 17 games into year two, short-circuiting any chance his $10 million vesting option for 2009 could become guaranteed.

Sosa’s run in the Windy City did not come complete with a fairytale ending, either. In 13 seasons with the Cubs, he hit 545 home runs, including 60 or more in a season three times. After signing a four-year, $72 million contract extension in 2001, Slammin’ Sammy slumped to .253/.332/.517 in 2004. When he walked out on the club before the final game of the season, general manager Jim Hendry began looking to trade his unhappy right fielder, a task complicated by the $25 million left on Sosa’s contract.

Hendry ultimately found trade partner in Baltimore, though the Cubs paid $16.15 million of the remaining money left on the contract. Sosa, for his part, agreed to eliminate language guaranteeing the $18 million club option for 2006 if he was traded. He also agreed to drop a provision adding a $19 million option for 2007 with a trade.

At the time of the trade, both Hendry and Sosa spoke optimistically about change and fresh starts. But now, five years later, Chicago Magazine has quoted Sosa as saying that the Cubs “disrespected” him by allowing other players to wear his No. 21. (Pitcher Jason Marquis wore No. 21 in 2007 and 2008, and it now belongs to outfielder Tyler Colvin.) So his messy exit clearly still touches a nerve.

The problem is as old as the game itself. Babe Ruth held out hope of managing one day. Jackie Robinson didn’t want to leave Brooklyn. Ozzie Smith never wanted to move off shortstop. Tom Glavine wanted one last chance to throw as a Brave. Regardless of the circumstances, telling a franchise icon that you’re moving on without him is one of the touchiest issues a front office can face.

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If Jeter can only muster an OPS around .700-.730, it will sure he hard to justify him in a lineup in the dangerous AL East. I just don't see a right answer for the Yankees this offseason.
I agree with you in theory but in practice it will be very easy for the Yankees to justify it to their fans. I'm not sure how low Jeter's OPS would have to fall before Yankee fans would be OK with someone else taking his spot but it's a lot lower than .700. I think Jeter will be overpaid and overplayed for the rest of his career and no one outside of SABR circles will give a hoot.
I'm a Yankee fan and LOVE DJ but this has been an ugly year - and getting uglier with each game. The problem is who is around to replace him? JJ Hardy? Yeesh. Look at SS eligible players with 200+ ABs and Jeter is 15th - a perfectly league average SS; which says as much about the state of SS's than it does about Jeter. Maybe take a stab at trading for Brendan Ryan - at least his glove has value and if he gives you a .700 OPS then you are on to something.