Boom Or Bust: All-Time Best & Worst Free Agent Pitchers

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Each year Major League Baseball franchises evaluate the free agent pitcher market in an attempt to strike it rich. Sometimes teams strike it just right when they land a future Hall Of Famer. While other teams get absolutely no positive return on their investments. It can not be described as an exact science, in fact it’s as much of a crap shoot as any transaction in baseball due to the fact that a pitcher’s career could end after any one particular pitch.

Next season there are an amazing amount of talented starting pitchers available via free agency. The likes of David Price, Mat Latos, Johnny Cueto, Jeff Samardzija, Yovani Gallardo and Ian Kennedy can be signed by any team. The list grows even stronger when you add names like Tim Lincecum, Jordan Zimmermann, Doug Fister, Mark Beurhle, Bartolo Colon, A.J. Burnett, Tim Hudson, John Lackey, Bud Norris, Rick Porcello, and Justin Masterson. Next year’s class is unprecedented, and surely one or two teams will be on the wrong side of a contract. It’s no knock on these pitchers, it’s just a numbers game and the fact starting pitchers fade every season.

In the wake of Max Scherzer‘s seven-year, $210 million dollar deal, let’s take a closer look of some of the best and worst free agent pitcher signings in Major League history. No relief pitchers were considered for the following rankings. The parameters for the list are most/least value gained by the franchise through the whole contract. There are many different factors when determining value, since this list is for an individual accolade, then postseason victories and team championships are not the sole qualifications. This list is strictly an opinion and I invite you to add to the list yourself. Whom else deserves the distinction of being a boom or bust free agent acquisition? The top 5 for each category will be displayed.

Mandatory Credit: Ed Szczepanski-USA TODAY Sports

BUST

The worst all-time free agent signings of a major league starting pitcher. Total years of the contract and total amount paid overall wasn’t the only determining factor for this list. Production and health are key factors as well. If a player signs a $100 million-plus contract, I am not going to automatically deem the contract a failure. However that player should at least be available and play the whole tenure of the contract. Remember this is an opinion not to be misconstrued as fact.

HONORABLE MENTIONS

Kevin Brown (1999) Los Angeles Dodgers 7 years-$108 million

Barry Zito (2007) San Francisco Giants 7 years-$126 million

Chan Ho Park (2002) Texas Rangers 5 years-$65 million

Mandatory Credit: Jon Soo Hoo/Dodgers

#5 Darren Dreifort, Los Angeles Dodgers (2001) 5 years-$55 million

Despite a 39-45 career record and a history of arm problems, the Dodgers decided to sign Darren Dreifort to a five-year contract after the 2000 season. Even though he was already a Dodger, he was allowed to declare for free agency, thus qualifying for this list. Super money agent Scott Boras sold the Dodgers on the fact Dreifort had tremendous upside and youth.

Boras also reportedly told Dodger management Dreifort was close to signing with the rival Colorado Rockies. That was enough, and the Dodgers yet again invested millions of dollars on their pitching staff. Dreifort almost immediately hurt himself after inking the contract. The five year totals were 204.7 innings, a 4.64 ERA , 1.53 WHIP and a 9-15 record. That’s a whopping $6.1 million dollars for each win! What a horrible contract.

Mandatory Credit: NYDN.com

#4 Roger Clemens, New York Yankees (2007) 1 year-28 million

On May 6th, 2007 during the 7th inning stretch of a Yankee game, Roger Clemens appeared in George Steinbrener’s owner’s box. Shortly thereafter, it was announced the 44-year old would sign a one-year, $28 million dollar contract. Clemens was clearly on the downside of his career and failing to show for spring training (let alone the month of April) rubbed some of his Yankee teammates the wrong way.

He would go on to compile a 6-6 record and a 4.18 ERA for the Yankees who failed to win it all. That works out to roughly $4.7 million per month prorated, or slightly over $1 million dollars per start! What a horrible investment made by the free-spending Yankees. To essentially rent a player for six months and disturb the harmony in your clubhouse. Tisk Tisk

Mandatory Credit: vincesbaseballblog.wordpress.com

#3 Carl Pavano, New York Yankees (2005) 4 years, $39.95 million

Often hurt and dubbed “American Idle” by the New York Media, Carl Pavano was another mistake by the New York Yankees. Perhaps it was his 2003 World Series (Game 4) masterful performance against the Yankees that first started their infatuation with him.

Despite posting an 18-8 record and 3.00 ERA ( in 2004 for Florida Marlins) the Yankees got hosed by Pavano as he only managed 26 total starts in his four years in Yankee pinstripes. He finished his tumultuous Yankee career with a 9-8 record and a 5.00 ERA to go with a 1.455 WHIP. At $1. 54 million per start, and a ridiculous $4.44 million per win for the Bronx Bombers, Pavano definitely makes this list. He was ushered out of New York with a round of applause as the Yankee faithful could not wait to get rid of this underperformer.

Mandatory Credit: bleacherreport.com

#2 Mike Hampton, Colorado Rockies (2001) 8 years-$121 million

In shear size alone, this contract seemed horrible from the start, factor in the length, and it is just plain old silly! After aparentley missing out on the Darren Dreifort sweepstakes the Colorado Rockies decided to make a huge splash in the free agent market.

Hampton only lasted 2 seasons in Colorado, and posted a 21-28 record with a 5.75 ERA and a mind-blowing 1.677 WHIP. In 79 games with the Rockies, he did club 10 home runs as a pitcher. He only spent two out of the eight years in Colorado, and had some decent years with the Atlanta Braves, but $15.125 million per year for Hampton was horrible. At $1.44 million per win in his two years in Colorado, Mike Hampton is #2 on the list.

Mandatory Credit: espn.go.com

#1 Jason Schmidt, Los Angeles Dodgers (2007) 3 years-47 million

Despite a steady decrease in velocity, the Los Angeles Dodgers attempted to steal their rival’s best pitcher. Schmidt was indeed the San Francisco Giants’ best pitcher, but those in and around the baseball world were well aware of his dip in velocity. Schmidt was a power pitcher and without his four-seam fastball in the high 90’s, he was nothing more but a shell of himself.

After his third start as a Dodger, Schmidt came out with shoulder issues. He ended up missing 1 1/2 years after getting his shoulder completely rebuilt. In 2009 he briefly played again, but ultimately hurt his shoulder and was forced to retire.

Career for the Dodger….10 starts and a 3-6 record with a 6.02 ERA and a 1.708 WHIP. Schmidt earned $4.7 million per start and a HORRENDOUS $15.7 million per win! Even though this wasn’t a long commitment or $100 million dollar contract, in sheer value this was the worst free agent pitcher acquisition in the history of the game.

Next: Any Free Agents That Can Help The Padres?

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