At the end of every year, after the champagne has been cleaned from the World Series Champion’s clubhouse, a number of exemplary players are recognized for their hard work, skill, and entertainment value. The MVP or Cy Young are the belle of the ball and they receive much recognition.
Under the right circumstances, these individual honors can translate into some seriously bloated contract offers. And in some years you don’t even have to be good so long as you play a position in which the market is weak. Pitchers often show up on lists like this and you’ll find no shortage of them here, but there’s plenty of position player mistakes to go around too.
While we blame the players if they don’t perform, there is also a lot of responsibility that ends up on the shoulders of those who brought them in in the first place. GMs come and go and those who are lucky or smart get to stick around despite their influence on the free agent market and the deals they make that implode. You’ll see a few of them mentioned below.
The following list is littered with players that wowed us, sometimes contributed to compelling stories and either lived up to and beyond their compensation or made you want to call up Blo Bros. (1-800-4-A-Potty) and suck up the stink. Here are 8 free agency signings that worked and 7 that didn’t.
15. Worked – Bartolo Colon (Mets)
Bartolo Colon won the Cy Young in 2005 at the age of 32. He won 21 games. Over the next four season, he totaled 14 wins with a collective 5.18 ERA. In 2010 he didn’t even show up. By then most of us thought he was retired. It came as a surprise then, when Brian Cashman signed him in 2011 for the Yankees. It wasn’t Cy Young Colon, but he was back and it confused us.
It wasn’t until 2012 though, when Billy Beane of the As sniffed a bargain, and the subsequent year that we realized this wasn’t one last golden summer. Bartolo had opened up a new treatment with platelet-rich plasma therapy. Some cried foul and others became engrossed in the story of an old man turned young again. He continued to turn our disbelief into pure joy as a fat, grinning 41,42,43 year old pitcher with the Mets, culminating in a magic home run on May 7th in 2016 (then as a 42 year old).
14. Didn’t Work – Carl Pavano (Yankees)
Brian Cashman makes the list again as the signing GM of a bad contract. His presence throughout this list is more due to the Yankees way of business and the influence of “The Boss” – buy everyone worth buying, whatever the cost. Carl Pavano was worth buying and it cost the Yankees $39.95 million for four years of control.
Hindsight being 20/20, the Yankees would not have signed Povano for what ended up costing them $4,438,888 per win. Carl, like other busts on this list, was betrayed by his body and missed significant time.
13. Worked – Roger Clemens (Blue Jays)
The Rocket is a great case for the other side of the risk management coin, opposite Barry Zito. In 1996, Red Sox GM Dan Duquette tried to sign Roger to a generous contract, hoping to keep him a Red Sox through “the twighlight of his career.” Clemens spurned the Sox and went to Canada to pitch for GM Gord Ash and the Toronto Blue Jays. He was basically the best pitcher in baseball for two years before being traded to the Yankees.
Roger won four Cy Young awards after leaving the Red Sox. He won 162 games A.B. (after Boston) and picked up a couple of World Series rings with the Yankees. He even retired, like four times. Who gets away with that? Roger Clemens does, because he was good and someone wanted him.
12. Didn’t Work – Barry Zito (Giants)
By the time Zito became a free agent, he had three all-star nods and a Cy Young award under his belt. In the six full seasons leading into free agency, Barry had thrown over 1,300 innings with an average of just under 223 innings per year. Not a lot of guys could do that. He was armed with a curveball that, at the time, was considered the best in the game.
This is why, in 2007, GM Brian Sabean of the San Francisco Giants signed Zito to a 7-year, $126 million dollar contract. It was the largest contract ever for a pitcher and became a perfect case in risk management. On one side, you have some of the best production in the last six years, expecting it to project for at least the next three or four years until age and wear and tear catch up. It happened almost immediately and the Giants got third or fourth starter production for the price of an ace.
11. Worked – R.A. Dickey (Mets)
Omar Minaya signed Dickey to a minor league contract in 2010. He couldn’t have known then that the knuckleballer would earn all-star honors and bring home the Cy Young award in 2012. This production on an extremely team-friendly contract made R.A. one of the better bargains in a long time.
Then it got even better. After the 2012 season, R.A. was traded to the Toronto Blue Jays where he gave them good production and lots of innings, but didn’t measure up to his Mets days. In return, New York got Noah Syndegaard. “Thor”, as Syndergaard is commonly referred to, is now the backbone of a young and talented Mets rotation.
10. Didn’t Work – Carl Crawford (Red Sox)
Finally, a position player! Bostonians and other Sox fans would prefer that he wasn’t brought up again, but we can’t have this list without including one of our biggest disappointments. We were so excited to have such a dynamic ballplayer. A high batting average, some power, and tons of stolen bases. The SBs were something new to the Sox and on the flip side Carl wouldn’t be stealing 3 or 4 bags a night on us. So we gave him $142 million on a seven year contract.
Crawford ended up playing well below his standards, was oft injured, and became a sullen baby due to the “toxic” Fenway Faithful. Lucky for the Sox, the Dodgers became the new Yankees and took both Carl and Adrian Gonzalez off our hands. Adrian was a good player, but Carl was the price of admission.
9. Worked – Alfonso Soriano (Yankees)
Soriano was an unknown player when he burst onto the scene for New York. He gave them three awesome seasons before being traded. It was shocking because this was the sort of player the Yankees would never let get away. He was traded for A-Rod and cash considerations – probably a deal every GM in baseball pulls the trigger on, but still. In Soriano’s 3 full seasons with the Yankees he hit 95 home runs and stole 119 bases.
Soriano was an All-Star for five consecutive seasons after his trade. He hit another 291 home runs for the Rangers, Nationals, and Cubs to go along with another 161 stolen bases. While A-Rod won 2 MVPs and helped the Yankees to the World Series title in 2009, it’s legitimate to wonder if Cashman would like a do-over on the deal that brought New York baseball’s greatest all-around dink.
8. Didn’t Work – Jason Bay (Mets)
Jason Bay was NL Rookie of the Year and a three-time All-Star before he got his first crack at free agency after the ’09 season. The Red Sox wanted him back and offered him arbitration, but he declined and tested the waters. The New York Mets gave him a four-year, $66 million dollar contract. The Sox received the 39th and 57th pick in the 2010 first-year player draft as a result.
Although the picks ultimately did not greatly help the Sox they must have breathed a sigh of relief that they were not tied down to a contract that was basically worthless. Bay was also Boston’s way out of the Manny Ramirez experiment as he was involved in the trade that brought them Bay in the first place. If nothing else, Bay was addition by subtraction.
7. Worked – Robinson Cano (Mariners)
Like Alfonso Soriano, Cano’s is a case where everything made sense except his employer. By the time he hit free agency Cano was a five-time All-Star, five-time Silver Slugger, and a two-time Gold Glove recipient. Again, just the sort of player that New York would overspend for if he was a free agent from another team. How could they let someone this talented on both sides of the ball walk?
When Cano signed with the Seattle Mariners we thought he and the Mariners had made a mistake. $240 million over 10 years is a long time and a lot of money. Perhaps Cano thought he’d retire at the end of the contract and therefore didn’t have to worry whether Safeco Field would drain his power and ability to land another lucrative contract. Seattle wasn’t worried about it and he rewarded them last season with 39 home runs and an 8th place position on the MVP ballot.
6. Didn’t Work – Andruw Jones (Dodgers)
Andruw Jones was arguably the greatest center fielder of his time. This was a time that included guys like Ken Griffey, Jr. and Torii Hunter. He won 10 consecutive Gold Glove awards, garnered 5 All-Star invites, and was in the top 16 or better for MVP on five separate occasions. He and Chipper were Gods in Atlanta.
After the ’07 season, Jones signed a two-year, $36.2 million dollar deal to play for the Dodgers. He played in 75 games and hit 3 home runs. Andruw felt like a gift to baseball fans and we felt it when the wheels fell off. He never played a full season again and we were left to wonder, what if?
5. Worked – David Ortiz (Red Sox)
In 2002, Terry Ryan, then GM of the Minnesota Twins, did the Boston Red Sox the greatest favor anyone ever has. He released Big Papi. Every year that decision looked worse and worse, starting with year 1 when Papi came in 5th place in the MVP race. Theo Epstein could not have known what David was going to become when he signed him to a $1.25 million dollar contract.
Besides becoming a favorite son of Boston, and standing up for the city in a moment that will forever mark American patriotism and defiance, the man could hit. He averaged just under 35 home runs a season for the 14 years he spent with the team. He was a 10-time All-Star, was the pre-eminent DH of his time, and did as much as anyone and more to end the curse of the Bambino.
4. Didn’t Work – Kevin Millwood (Rangers)
Kevin Millwood was never really a great pitcher. He gave up a lot of home runs and generally had a high ERA. He did pitch a lot of innings which was probably why the Texas Rangers gave him $60 million dollars on a 5-year contract. He pitched 2 games over .500 for Texas before being traded to Baltimore where he promptly lost 16 games. At least the Rangers got out before that mess of a season.
There’s not much more to say about Millwood. He had a good, never brilliant, career that ultimately led to 169 wins in 16 seasons. He’s a great example of why it pays to be a starting pitcher in the Major Leagues.
3. Worked – Jose Fernandez (Marlins)
Due to a complication in his high school years, Fernandez came close to being a free agent rather than draft-eligible. Since he won his appeal to join a U.S. high school this ends up being a cheat entry. Fernandez was, in short, the most electric and invigorating personality to join the game in a long time. Like other players from Cuba, Jose was known for his sense of flash and fun.
Before his tragic death in 2016, the Marlins pitcher compiled a 2.58 ERA over four seasons to go with a Rookie of the Year award and two All-Star appearances. There surely would have been many more accolades had his career not been shortened by both injuries and a terrible boating accident.
2. Didn’t Work – Joe Mauer (Twins)
The Minnesota Twins never let Mauer hit free agency. Perhaps, they should have. They may have been outbid and later relieved when they saw someone else overpay for a great catcher that once hit 28 home runs. He was a 3-time batting champ at a premium position so no one was really surprised when GM Bill Smith gave him an 8-year, $184 million dollar extension.
The assumption was that on top of being a great pure hitter, Mauer now had power and that would translate even after his legs couldn’t take the beating of being a catcher any longer. If Mauer had continued to play catcher you could almost justify the contract even when the power never came back. Instead, he hasn’t played the position since 2013 and the Twins have a first baseman who can’t hit a dozen home runs in a season. Ouch.
1. Worked – Francisco Rodriguez (Brewers)
When Rodriguez signed a one-year deal to pitch for the Milwaukee Brewers in 2014, he was five years removed from his last All-Star appearance. He wasn’t the K-Rod of old, but he got the job done. He parlayed the 44 save ’14 season into a nice $13 million dollar, two-year deal.
After another successful season in 2015, Rodriguez was traded to the Detroit Tigers where he continued his impressive work. Thanks to his career revival in Milwaukee and Tigers, along with a glittering four-year stretch during his time with the Angels, Francisco now sits in fourth place on the all-time saves list.
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