How We Got Here: Why Jake Peavy May Be the Least-Liked Ballplayer in Chicagoland

Okay, maybe he isn’t the most disliked person in the area, but in the sports scene, it’s got to be pretty close. Peavy, the 2007 NL Cy Young award winner, spent 9 months (July 08-April 09) being teased in a trade to the Chicago Cubs. Yesterday Peavy’s team, the San Diego Padres, reached an agreement to trade the pitching whiz to the Chicago White Sox in exchange for a few highly touted prospects. The problem: Peavy has a full “No-Trade” clause. So, because he didn’t want to play for the ChiSox, he vetoed the trade.

How did we get here? How did a perennial Cy Young candidate on a perennial losing team decide to turn down offers to two Chicago teams, both who made the playoffs last season? Let me walk you through the saga:

The Contract Situation: Peavy plays for the small-market San Diego Padres, beginning his career in 2002. After putting up solid, but not great numbers in his first season and a half, Peavy posted a stellar 2004 campaign, winning 15 games with a 2.27 ERA. The 2005 season was his final season that he was contractually obligated to be with the Padres, so in February before the 2005 season began, Peavy signed a four-year, $15M contract to stay with the Padres. The contract was set to expire after the 2008 season, unless the club exercised a $9M to retain him in 2009. In 2005, the Padres had a $70M payroll and the team went 82-80 and won the NL West for the first time since Tony Gwynn retired.

His 2006 campaign was decent, but a lack of run-support created a situation in which Peavy went 11-14, but with a decent 4.04 ERA. He responded, though, with his Cy Young winning year, as he won 19 games with a 2.54 ERA. It was clear to the Padres at this point that they needed to resign the 26 year old superstar. In December 2007, he signed a 3 year, $52M extension with the club with a contract which was supposed to be a model for all small-market clubs to retain their superstar pitchers. This deal was to take effect in 2010, giving the Padres temporary finance capability in return for a full “No Trade Clause”. This season, the Padres won 89 games.

Where Things Go Bad: In 2008, the Padres’ owner John Moores began divorce proceedings with his wife. While this normally is not big “sports” news, but combining this news with the economic downturn, the Padres’ brass was told to trim their 2009 payroll down from $73M to $40M. The Padres were stuck in a fire sale, and with Peavy not only as being the highest-paid player, he also had an iron-clad extension in place for 2010. Due to the economic uncertainty in 2008, potential trade candidates for Peavy were limited to big-market, high-payroll teams. This, coupled with Peavy’s “No Trade” clause and his vehement desire to play for National League teams because of his love for hitting, limited the candidates basically to four teams: Los Angeles Dodgers, New York Mets, Atlanta Braves, or the Chicago Cubs.You could narrow out the Dodgers because they would be overcharged due to the club being in the same division as the Padres. You could cross out the Mets, because the Mets' owner had lost a bit of money in the Bernie Madoff scandal, and had just signed lefty Johan Santana to a huge deal prior to the '08 season. This left two teams: the Atlanta Braves and the Chicago Cubs.
The Peavy-to-the-Cubs Saga:  After the 2008 season, the Cubs were believed to be strong suitors for Peavy’s services. They fit all of his criteria: NL team, big market, etc. The issue was the Padres’ acceptance of the Cubs offers. Many believe the Padres were posturing to get a better offer from the Atlanta Braves. The Braves decided to go in a different direction after feeling the Padres' asking price was too much, coupled with the bidding war with the Cubs. So, the Braves responded by signing pitcher Derek Lowe instead to a 4 year, $48M contract. This posturing by the Padres ultimately killed their chances with the Cubs. After all, if you were the Cubs and had no competition for Peavy, why would you still offer the same deal? By spring training, the deal was dead.

The Padres Ownership Change & The Chicago White Sox: Former agent Jeff Moorad in 2009 successfully purchased the Padres from owner John Moores. After his acquisition, he made no bones about it: he wanted to keep Jake Peavy. This season the Padres-though, after a hot 9-3 start, began to cool, losing 19 of their next 23 games. Moorad and GM Kevin Towers, began to look for suitors for Peavy, looking to ‘sell high’ rather than waiting for the trade deadline and looking desperate to shed Peavy and his $52M over the next three years.

The pitching-starved Chicago White Sox yesterday made an offer and agreed to a deal, sending at least two of the team’s highly rated prospects to the Padres in exchange for the Cy-Young winner. The deal was as good as done, except for the fact that Peavy has his “No Trade Clause”. He ultimately chose not to join the White Sox, because that’s what he and his family decided, and no one can really fault him for that.

So, two failed trade attempts later, and Peavy may be the most disliked sports star in the Chicagoland area. Though, one could argue, he can’t be blamed for either. The first trade to the Cubs fell through because GM Towers overplayed his hand and ultimately lost any leverage in negotiations. The White Sox trade fell through because he asked (and had the right to ask) to be traded to a National League team. I find this commendable, more so because I disagree with the designated hitter role in the American League, and applaud Peavy for wanting to play the whole game—pitching and hitting.