Who Are Baseball’s Worst And Best Free Agent Signings Of All Time??? Part 2

2nd Of A 3-Part Series On Free Agent Signings 

Today:  The Worst

(10 Thru 1)

Thanks to the courageous stand taken by Curt Flood and Andy Messersmith back in the mid 1970’s,  today’s baseball players have been released from captivity.  They no longer must remain with the team that signed them to their first major league contract.

Freedom of movement was created.  And predictably salaries have skyrocketed.  It’s an agent controlled auction.  Greed has consumed the game.  Agents have become wealthy.  Players have become multi millionaires.

Win At All Cost

The win at all cost  philosophy  is out of control.  Teams with deep financial pockets  rake in the superstars while the less fortunate suffer.  For so many summers it was the New York Yankees who wrote the biggest paychecks.

 Last summer however, the Los Angeles Dodgers spent approximately $300M on payroll.  They were beaten by the New York Mets in the National League Divisional Series.

The loser in all of this is Joe Fan. Although ticket increases varied, parking ,concessions and souvenir prices went through the roof. And strangely, the biggest spenders were not always the biggest winners. It still takes more than money to buy a World Series ring.

Over the years big dollars haven’t necessarily brought big successes. The disappointments are well documented. Some of baseball’s highest paid non-producers are players you might remember.

worst-free-agent-10No. 10 Gary Matthews, Jr.

Gary Mathews Jr. would have made a good travel agent. He might have seen more sights between March 23, 2000 and November 22, 2006 than Rick Steves.

After he made his major league debut with San Diego on June 4, 1999, Mathews barely unpacked his bags. His journey meandered through Chicago (.207), Pittsburgh (.245), New York (.186), Baltimore (.253), San Diego (again! .266), Atlanta (never played a game) and Arlington, Texas (.285).

Perfect Timing

Mathews did however, save the best for last. During his free agent season with the Rangers, Mathews put up impressive (?) numbers while playing in 147 games. He hit 19 home runs, drove in 79 runs, batted .313 and had an OPS of .866.

They impressed the the Angels, who signed the San Francisco native to a whopping 5 yr, $50M contract.

His three years in Anaheim were a disaster. He hit a poultry 30 home runs, drove in only 168 teammates and saw his OPS almost disappear (.708).

On January 22, 2010 the Mets gave him a second chance after owner Arte Moreno threw in some cash. After 35 games  in New York, he was on to Cincinnati  for one month before finally being release for good on July 24, 2010.

Mathew cashed his final $10M paycheck from the Angels in 2011. He was the epitome of a ONE YEAR WONDER!

Major League Record?

worst-free-agent-9No. 9 Russ Ortiz.

Russ Ortiz may hold the major league record for most free agent signings. During his 12 years in the big leagues, the 6’1, 200 pounder inked seven free agent contracts.

Originally drafted (June 1, 1995) and signed (June 14, 1995) by San Francisco, Ortiz had a very successful first six years in the major leagues. His record in his first stop with the Giants was 67-44.

Yet on December 17, 2002 he was dealt to Atlanta where he promptly won 21 games (he lost seven) his first year as a Brave. He was 36-16 during his two year stay in Atlanta and that led to a healthy 4 yr, $33M free agent offer from Arizona.

Injuries Followed…

During his stay in the ‘Valley Of The Sun’, injuries clouded his career. Ortiz won five and lost 16, pitching in only 137.2 innings while his earned run average ballooned to 7.00. So bring on the gamblers and let the free agent parade begin.

First stop, Baltimore (0-3). Then back to San Francisco (2-3). On to Houston (3-6). Ortiz was also signed by the Yankees and Colorado in 2009 but never pitched for either team. Last stop was Los Angeles (0-2) and on April 22, 2010 his career was over.

worst-free-agent-8No. 8 Carlos Silva.

Carlos Silva was the lunch pale type of pitcher. He had a very pedestrian record (70-70) and a very workman like career which saw him average 138 innings over nine years. One really good year, one really bad year.

The Phillies drafted Silva and signed him on March 22, 1996. During his two year stay in Philadelphia, Silva won 8 of 9 games and posted a 3.83 ERA.

After being acquired by Minnesota on December 8, 2003, the right hander posted a record of 14-8 in his first season in the Twin Cities. Although his four seasons with the Twins produced a non-spectacular 47-45 record, Seattle saw something they liked.

Bad Eye Sight

The Mariners signed Silva to a robust 4 yr, $48M contract. Their reward? A record of 4-15 and an ERA of 6.46! He followed that up with a 1-3 record to go along with a 8.60 ERA and on December 18, 2009  was traded to the Cubs for another under achiever, Milton Bradley.

Although he was 10-6 for Chicago, Silva was released, He was subsequently signed and released by the Yankees in 2011 and Boston in 2012. Carlos was a mediocre pitcher who nonetheless made a nice little living.

worst-free-agent-7No. 7 Chan Ho Park.

Rated the 14th best prospect in 1994 by Baseball America, Chan Ho Park was signed by the Dodgers on April 8 that year. Part of the Far East Influx, Park was an immediate hit with the huge Korea Town population in Los Angeles.

It was a media frenzy every time Park took the Dodger Stadium mound. Perhaps the circus atmosphere effected Park initially. He pitched in only two games with no record in both 1994 and 1995. Despite the hysteria, he got his feet wet with a 5-5 record in 1996.

After that season, there was no stopping Chan Ho. Between 1997 and 2001, Park blew the National League away. He won 75 games, lost only 49 with a yearly earned run average that never exceeded 3.71.

And with that consistency Park was able to command big bucks on the free agent market. Texas won the bidding war, signing Chan Ho on January 16, 2002 to a 5 yr, $65M deal.

Never Got Their $$$ Worth

But like so many other monster signings, Park never returned the investment. His records in 2002 (9-8, 5.75 ERA), 2003 (1-3, 7.58) and 2004 (4-7, 5.64) were extremely disappointing to say the least. And after starting 2005 with an 8-5 mark and 5.66 ERA, Park on July 30 was traded to San Diego.

After less than two years with the Padres produced an 8-5 mark accompanied by a 5.66 ERA, Park on June 3, 2007 was released.

After failing to impress the Mets (0-1), Dodgers (again, 4-4) Phillies (3-3) and Yankees (2-1), Park was traded midway through the 2010 season Pittsburgh. He pitched last game on October 1, 2010 against Florida. Chan Ho could never recapture the magic that he discovered during his first tour with the Dodgers.

worst-free-agent-6No. 6 Carl Crawford.

Carl Crawford was the epitome of a true 5-tool player. In other words, he could DO IT ALL! The Tampa Bay Rays may have pulled off one of the biggest heists in baseball history when they drafted Crawford on the second round of the 1999 amateur draft.

Was every other team sound asleep? This belongs in ‘Ripley’s Believe It Or Not’. Proudly, Tampa Bay quickly got Crawford’s name affixed to a contract on June 14, 1999.

Impressive Credentials

In six of his nine years with the Rays, Crawford played in at least 151 games. Five times he stole more than 50 bases, highlighted by his 60 thefts in 2009. On five other occasions his OPS exceeded .800. It peaked at .851 in 2010. Five more years he hit over .300, reaching .315 in 2007.

By the time he reached free agency on November 1, 2020, everybody else had awakened.

All the big money players threw their hats into the ring. And the winner was? The Boston Red Sox. They won the opportunity to pay Crawford $142M over 7 years. Unfortunately, injuries started to rear its ugly head.

His first year in Beantown, Crawford played in 130 games. He hit .255, swiped only 18 bags and had an embarrassing OPS of .694. As difficult as it would be, things actually got even worse.

In 2012 he was a mere shadow of his former self, appearing in just 31 games. On August 25, 2012 Crawford was part of a nine player, blockbuster trade with the Dodgers. The deal wasn’t actually finalized and completed until October 4.

In his three years as a Dodger, Crawford has played in just 290 games, including 69 last season. His batting average is .286. He has just 48 steals and an OPS of .742. At 34, Crawford’s health remains the big question. That and how much gas is still left in his tank.

worst-free-agent-5No. 5 Melvin Upton, Jr.

Known as B.J. until recently, Melvin Upton Jr. was the second overall selection in the 2002 amateur draft. After drafting Upton, Tampa Bay signed him on September 16, 2002.

A durable outfielder, Upton played in at least 144 games from 2008 to 2012. He also had at least 31 steals every one of those years. And between 2007 and 2012 his OPS was under .700 just once. In 2009 it slipped to .686.

Family Reunion

In those eight eight years with the Rays however, his batting average was just .255.

Perhaps Atlanta felt a reunion with his brother, Justin might kick start his career. So on November 29. 2012 the Braves wooed Upton with a 5 yr. $75.25M contract.

Yet sometimes the best laid plans of mice and men fail. Such was the case with Milton.

In 267 games during his two year stay in Georgia, Upton batted .198, hit 21 home runs. drove in 61 runs, had an OPS of.593 and on April 5, 2015 was shipped to the Padres.

Perhaps it’s curious that although Upton hit a microscopic .259, slugged (?) five home runs a knocked across only 17 teammates in 87 games for San Diego last season, he is still one of the most sought after free agents this winter.

His resume however, might not produce the big money the 31-year old outfielder is seeking. Time will tell.

worst-free-agent-4No. 4  Andruw Jones. 

The Atlanta Braves signed Andruw Jones on July 1, 1993. Jones career wasn’t exactly something that you’d write home about. He spent his first 12 seasons in Georgia, and didn’t exactly tear major league pitching apart. With the exception of 2000 when he hit .303, Jones never exceeded .277 (2003).

Ironically,  his final season as a Brave was perhaps his least productive. His .222 batting average was his lowest since his rookie season (1996) when he hit .217. His OPS of .724 was also lowest since his rookie season (.709). But to his credit, Jones deposited 26 fair balls outside the playing field and drove in 94 runs.

Numbers Plummeted

He obviously impressed the Dodgers. They inked Jones to a 2 yr, $36.2M contract. Los Angeles probably expected to get more than 75 games in return for their investment. After all, from 1997 through 2007 Jones never played in less than 153 games.

But things got even worse. In his only season on the West Coast, Jones’ numbers plummeted. Hit hit a grand total of three home runs, drove in 14 runs, had an OPS of .505 and a batting average of .158.

His accomplishments were indeed underwhelming!

Released by the Dodgers, Jones signed with Texas on February 8, 2009 where he hit 17 home runs, drove in 43 runs and batted .214 in 82 games.

Next stop was the White Sox where his line was 17/43/.231 in 107 games. In his final two years with the Yankees Jones hit 27 home runs. knocked in 67 and hit .220 in 171 games.

The end came on October 29, 2012 when Jones was released.

Neagle Blossomed

No. 3  Denny Neagle.

Signed on June 22, 1989 by the Twins, Denny Neagle pitched in a grand total of seven games spanning 20 innings that resulted in a record of 0-1 before being traded to Pittsburgh in 1992.

He started coming out of his shell in 1995 when he was a 13-game winner. He improved to 14-6 the following year.

Traded to the Braves on August 28, Neagle blossomed in 1997 when he became a 20-game winner (he lost five). He followed that up with a 16-11 mark the next season.

Give Me The Money!!!

Two years in Cincinnati (17-7) and one summer with the Yankees (7-7) for some inexplicable reason earned Naegle a 5 yr, $51M contract with Colorado.

It wasn’t the arrival of the savior the Rockies had hoped for.

In his first three seasons in Denver, Neagle was 9-8 with an ERA of 5.38,  8-11, 5.26 and a swan song season of 2-3, 7.90.

He didn’t even pitch in 2004 and was released on December 6. He actually signed with Tampa Bay on February 7, 2005 but never pitched there either.

worst-free-agent-2No. 2  Mike Hampton.

Signed by Seattle on June 4, 1990, Mike Hampton had an uneventful 1-3 record in his only season with the Mariners and was dealt on December 10 to Houston. It was his coming out party.

From 1996 through 1999, the 5’10 185 pound lefty flourished. He went 58-31 those four seasons, including a mark of 22-4 in his final year before being shipped off to he Mets.

YOU CAN’T BUY SUCCESS

After going 15-10 in New York, Hampton followed Denny Neagle to Denver. On December 12, 2000 Hampton sent the whole free agent market back on its heels.

He signed a staggering 8 yr, $121M contract that had the industry reeling. Within eight days, Colorado had gone to the vault for $172M in hopes of bringing a world championship to ski country.

As impressive as those figures were, the games are played on the field, not on paper.

When the dust had cleared, all Denver had to show for its wheel barrels full of money was a record of 82-80. That was good for fourth place in the National League West, 15 games behind the division winning Giants.

Hampton accumulated a 21-28 record during his two year stay with the Rockies. Colorado basically paid him approximately $5.76M PER WIN, YIKES!

Over the course of two days in November, 2002 Hampton went from Denver to Florida to Atlanta. After achieving a 35-24 record during his first three years with the Braves, Hampton missed the entire 2006 and 2007 seasons with injuries.

Drysdale Weighs In

This reminds me of a conversation I had over dinner with Hall Of Fame pitcher Don Drysdale in the press room at Texas (Arlington) Stadium during the early 1970’s when free agency was in it infancy.

Drysdale, a member of the Angels broadcast team, was very adamant in his belief that because of the wear and tear pitchers are subjected to in their shoulder, arm and elbow, they should never be offered more than a two year contract.

After missing those two seasons, Hampton returned with a thud! In 2008 he pitched in just 13 ineffective games (3-4, 4.85) and was on his was back to the Astros.

He was 7-10 in his not so triumphant return to Texas and wound up his career the following season with a token appearance in Arizona (0-0, 10 games) before retiring December 8, 2010.

worst-free-agent-1No. 1  Josh Hamilton.

Josh Hamilton was signed by the Tampa Bay on June 3, 1999. His well documented alcohol and drug addiction story delayed the start of his major league career.

In 2006 he was a Rule 5 draft selection by the Chicago Cubs. The same day he was drafted by the Cubs, December 7, he was purchased by Cincinnati.

In 90 games with the Reds his rookie season, Hamilton put up respectable numbers: 19 home runs, 47 RBI, and OPS of .922 and a batting average of .292.

It was his only season with the Reds.  He was dealt to Texas on December 21, 2007. He was an instant hit with the Rangers. In his first year, Hamilton cracked 32 home runs. drove in 130 runs, hit .304 and had an OPS of .901.

Two Most Valuable Player Awards

Two years later, Hamilton was named the American League’s Most Valuable Player. His resume included 32 home runs, 100 RBI, a .359 batting average and an out of sight OPS of 1.044. He was also named MVP of the AL Championship Series.

His final season with the Rangers again included extremely impressive statistics. Forty three home runs, 128 runs batted in and a .285 batting average and OPS of .930.

He was one of the winter’s most sought after free agents. The drama that played out was full of intrigue.

Hamilton and his wife Katie, were wined and dined by Angel owner Arte Moreno and wife Carole in Texas, The Hamilton’s were more impressed as the evening wore on.

Eventually Hamilton accepted the Angel’s 5 yr., $125M offer to come to Anaheim. But the feeling within the Angel organization was divided. Rumor had it that then general manager Jerry Dipoto was not on board with the decision.

MORENO V. DIPOTO

Although it was all smiles and everybody was gracious and kind and said the right words at the introductory press conference, which was attended by approximately 1,000 boisterous fans in the parking lot at Anaheim Stadium, the rift had already developed.

The owner and his general manager  weren’t on the same page. The organization tried to cover it up as best best they could, but the damage had already been done.

The friction wouldn’t go away. It followed Hamilton wherever he went. This was one wound that time couldn’t heal. Yet Hamilton was still able to put up respectable numbers during his first season in Anaheim.  In 151 games he slugged 21 home runs, drove in 79 runs and hit .250.

Hamilton played in just 89 games in 2014 and his production fell off considerably. Ten home runs, 44 RBI and a slightly improved batting average of .263 hardly warranted the money Moreno was paying him. His tour in Anaheim was, to be kind, a BUST.

To make matters worse, Hamilton relapsed during the winter and went into rehabilitation. But because he wasn’t suspended by Major League Baseball, Moreno still had to pay him.

There were rumors that the owner was furious. Almost as a last resort, Moreno took the only offer he got, from Texas. The Rangers only accepted the deal after Moreno agreed to chip in $60M to  help pay Hamilton’s contract.

Thus on April 27, 2015 they closed the book on one of the saddest chapters in Angel history.

This list was compiled by A.J. Eisma of MLB. com.

John Stellman

I was born with sports in my blood. I began coaching little league baseball at 15. I was the sports editor of my high school newspaper. I did football play by play for the college radio station. I broadcast high school basketball for a local commercial station. But baseball was always my passion. During the 1970's I covered the Angels for the Orange County Register. And now I am back where I belong...
John Stellman

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