It doesn’t take much effort or courage to second guess a player’s contract.  However, every once in a while, a deal is so awful that nearly everyone correctly pans it immediately after it was signed.  Today, we’ll look at three awful deals.

Barry Zito

Zito was a former Cy Young award winner and a lefty to boot.  After the 2006 season, the San Francisco Giants signed the free agent pitcher to a seven year contract worth $126 million.  So, what’s wrong with that?

Well, since that Cy Young year in 2002 (23-5 with a 2.75 ERA), he had been pretty mediocre, going 55-46 with a 3.83 ERA.  His numbers, across the board, were slipping.  He was giving up more hits, more walks, more homers, and was striking out fewer batters (strikeouts aren’t a panacea, but it you stop striking out people without compensating in another area, it’s going to hurt you).

In essence, a pitcher who began his career with aspirations of the Hall of Fame (47-17, 3.04 ERA in his first three seasons) appeared to now be just average, or maybe slightly above.  Unfortunately, the Giants were paying him ace money.

What happened?  Despite moving to the allegedly weaker National League, Zito’s numbers got even worse.  He went 11-13 with 4.53 ERA in 2007 and slid further to 10-17, 5.15 in 2008.  He was an utter laughingstock.  Zito bounced back a bit in 2009, posting a 4.03 ERA (along with a 10-13 record) while putting up improved numbers in other areas.  Three years into the deal, the pundits have been proven correct.  Zito will have to put up dominant numbers for the rest of the years in the contract in order for the Giants’ money to be well spent.

Gary Matthews Jr.

In 2006, Gary Matthews put up by far the best season of his career, hitting .313 with 19 homers and 79 RBI.  He was selected to the All-Star game and finished 30th in the MVP balloting.

His reward was a five year deal from the Anaheim Angels worth $50 million.  The baseball world was stunned.  Even with his 2006 season, Matthews had been a below average offensive player during the course of his career (posting a career OPS+ of 97, with 100 equating to an average player).

If Matthews had been a bit younger, the deal would have made more sense.  It could have been argued that Matthews was having a breakout year in 2006 – with more of the same on the horizon.  Matthews was 32 at the end of the 2006 season, though.  There’s a special term for “breakout” seasons that happen at that age.  Fluke.

After three lackluster seasons with the Angels which saw him as a part time player toward the end, Matthews was traded to the Mets with two years and $23.5 million remaining on his contract.  Also traded to the Mets in the deal was $21 million in cold, hard cash to offset Matthews’ contract.

Tom Glavine

Tom Glavine is, without argument, a future Hall of Fame pitcher and one of the best left handed pitchers of this era.  What’s he doing on this list?

After the 2007 season, Glavine was signed to a one year, $8 million deal by the Atlanta Braves, for whom he pitched during most of his career.  Although several of Glavine’s secondary statistics seemed to indicate that he was in decline (common for a pitcher of his age), the $8 million salary was not the problem.

The problem was that Glavine was a type A free agent.  The team losing Glavine would get the Braves’ 2008 first round draft pick (#18 overall) and well as a sandwich pick between the first and second round (which would end up being the #33 overall pick).  That meant that the team losing Glavine would get two potential building blocks for the future.

That all sounds pretty bad, huh?  Well, to make it even worse, the team losing Glavine (and gaining those picks) was the Braves’ bitter division rival, the New York Mets.  As someone who is quite familiar with the free agency compensation system, I very nearly spit Pepsi onto my monitor when I saw the Braves inflict this sort of damage upon themselves.

So, what happened?

Minor league expert John Sickels has the player picked at #18 (Ike Davis) as the #4 prospect in the Mets system and the player picked at #33 (Bradley Holt) as the 9th best Mets prospects in his 2010 Mets Prospects list.

As for Glavine?  Well, there really wasn’t much chance of significant upside for the Braves.  A 42 year old pitcher is always working on borrowed time.  But even I expected more than a 2-4 record and 5.54 ERA in 13 starts during his final stint with the Braves.

So, what were the Braves thinking?  It seems that they were blinded by sentimentality.  Glavine was a huge part of their success in the 90s, and it felt good to bring him back.  A front office with as much experience as the Braves should have made this decision with their head instead of their heart.

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Kosmo is the founder of The Soap Boxers and writes on a variety of topics. Many of his short stories have been collected into Kindle books.

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