With the MLB Hot Stove cooling off and with Spring Training about to begin I thought it would have been best if we brought ourselves back into the baseball world. The Offseason is where we see teams either make some big trades or some key signings. Over the last 20 years we have seen some huge signings like C.C Sabathia signing with the Yankees in 2009 and helping them win their 27th World Championship or in 2000 when Ichiro Suzuki signed with the Seattle Mariners and went on the win both the AL Rookie of the Year and AL MVP in 2001. These free agent signings can either make a huge difference for not only the team involved with signing the certain ball player but also the player himself. But in some cases these free agent signings can also not work out and the player doesn’t play well and the signing becomes a bust. For this week’s Top 10 list I will be ranking 10 of the worst MLB free agent signings of all time. I will be looking at how the player performed for their team and if they helped the team out for the long run. Also contract extensions are possibly going to be included as long as they were in the free agent market during the offseason. Comment below who you think was the worst signing of all time is and let’s countdown the Top 10 Worst MLB Signings of All Time.
Top 10 Worst MLB Signings of All Time
10. Daisuke Matsuzaka (December 2006, 6 Years, $52 Million with the Red Sox) – In 2006 there was a huge bidding war happening for Japanese Pitcher Daisuke Matsuzaka. He was one of the best pitchers at the time in Japan, winning 7 Gold Gloves in his first 8 seasons and he led the league in strikeouts 4 times and ERA 2 times and he won the Rookie of the Year in 1999. He was at the time the biggest free agent of the year and every team wanted in on him as they saw him as the next big thing in baseball. The Red Sox had the winning bid of $51.1 million dollars and would sign the starting pitcher to a 6 year deal worth $52 million. Daisuke Matsuzaka’s first season was pretty rocky as he went 15-12 with a 4.40 ERA with 201 strikeouts, but he still came in 4th place for AL Rookie of the Year voting while also winning a World Series ring. It wasn’t until the 2008 season where we got to see how really good Matsuzaka could be. He only started 29 games after missing a month with a shoulder injury but he finished the season with an 18-3 record with a 2.90 ERA and 154 strikeouts and came in 4th place in the AL Cy Young voting. That unfortunately would be the final season where we saw Dice-K be a dominant pitcher as his next 4 years in Boston he dealt with multiple different injuries including a hip injury, neck injury and an elbow injury where he had to get Tommy John surgery. After his final season in 2012 where he only went 1-7 with an ERA over 8 in just 11 starts the Red Sox would not re-sign him and he went off to become a free agent. He signed a minor league contract in 2013 with the Cleveland Indians before ultimately got released in August 2013 and then 2 days later after being released he signed with the New York Mets in which he spent the rest of the 2013 and 2014 season on and off of the starting rotation and spending time in the minor leagues. He later would return to Japan after spending 8 years in the MLB. While Dice-K’s first two seasons were really good, it was the fact that he dealt with nagging injuries and lost his ability to throw lights out stuff that made this contract signing a bust. It sucks really because this guy had some really good stuff but unfortunately all good things must come to an end. https://www.youtube.com/watch?v=I6ET_Q71GhA
9. Jacoby Ellsbury (December 2013, 7 years, $153 Million with the New York Yankees) – Jacoby Ellsbury is probably one of the best hitters/base stealers/outfield gloves when he is healthy. The time he spent with the Boston Red Sox is very memorable considering he helped the team win 2 World Series rings. He led the league in stolen bases 3 times during his 7 year run with the Sox and he also came in 2nd place in AL MVP in the 2011 season where he hit 32 homeruns, had 105 runs batted in and batted .321 with 212 hits and 39 stolen bases. It was a pretty incredible season for a guy who averaged less than 10 homeruns a season in just his first 4 years. But after the 2013 post season was over he signed with the enemy, the New York Yankees and signed a huge contract with them. Now the Yankees are known for signing huge contracts, just ask Alex Rodriguez and his 10 year $275 million how he is doing. Ellsbury signed a 7 year, $153 million dollar contract with an 8th year option that could have increased it to $169 million. The dude was apparently money at the time but how did he perform. In his first season with the Yankees he did actually pretty well. He hit .271 with 16 homeruns, 70 runs batted in and stole 39 bases. Not bad if you ask me. 2015 he was hit with the injury bug and his performance dropped as in just 111 games he hit .257 and only stole 21 bases while hitting only 7 homeruns. He bounced back the next season but his numbers were kind of similar. Then 2017 came and that’s where our story of why this contract was a bust begins. He went back and forth onto the disabled list, playing only 112 games and regulated on the bench by the 2nd half of the season. Coming in 2018 it was announced that Ellsbury wouldn’t be ready by opening day after he had an oblique strain in Spring Training. He missed the entire season due to the injury and would require surgery. Then the 2019 season began and Ellsbury was on the disabled list again but this time with a foot injury and then it was announced he had a shoulder injury and he missed the entire season for the 2nd straight season. He was then released during the 2019 offseason and the team still owed him $21 million for his 2020 salary. So from 2018 – 2020 Ellsbury was paid over $60 plus million by sitting at home. Talk about a bust as Ellsbury was a good player, when he was healthy. This deal is the worst Yankees signing of all time and is one of the worst contract signings in MLB’s history. https://www.youtube.com/watch?v=btXkMepSez8
8. Barry Zito (December 2006, 7 years, $126 Million with the San Francisco Giants) – While he might not be the most dominant pitcher of the 2000’s, Barry Zito has one of the nastiest curveballs in baseball history. He won the AL Cy Young in 2002 with the team that would be nominated for the Academy Awards, also known as the Moneyball 2002 Oakland Athletics. He won 23 games that year and also came in 13th in AL MVP voting. He was the best pitcher on the team, and in 2006 he became one of the hottest free agents on the market and later the highest paid pitcher in all of MLB when he signed a 7 year deal with the San Francisco Giants worth $126 million. His first year on the team was pretty slow and he had a record of 11-13 with a 4.53 ERA in 196.2 innings. All in all not bad but not great considering all the money he was being given to be the ace of the team. However he would have a losing record the next four seasons as he went a combined 32 – 48 with a combined ERA of 4.80. He bounced back and finally had a winning season in 2012 with a 15-8 record but the ERA was still above 4. In 2010 when the team won the World Series it was without Zito as he was not on the 25 man postseason roster for the Giants. He would get a ring for being a part of the team that year but still even if the man didn’t do so great, not having the highest paid player on the team is pretty sad. Luckily he made the roster in 2012 when the team won the World Series again. His final season with the Giants came in 2013 where he once again pitched poorly but Giants fans loved him for some reason. He spent his whole career in the Bay area of California with both the Oakland Athletics and San Francisco Giants, hence why he was fan favorite. While he wasn’t the greatest pitcher of all time he still was able to get one of the biggest contracts of the 2000’s and it might have been a bust for both the Giants and Zito’s career, but hey he still had a great time so A for effort I guess. I actually got to witness Zito pitch in person in 2006 against the Yankees in my first Yankee game in my life and I have to say it was cool seeing one of the worst signings in baseball history pitch against my Yankees. Giants might of gave up 120 plus million dollars for a pitcher to get 1 winning season but hey it’s all good, those 2 championship trophies still look good in San Fran. https://www.youtube.com/watch?v=FuysWEuO34Q
7. Carl Crawford (December 2010, 7 Years, $142 Million with the Boston Red Sox) – I mentioned Crawford in my Top 10 Players You Forgot Were Good list a while back as Crawford was once one of the best players in baseball. During his time with the Tampa Bay Devil Rays/Rays Carl Crawford was a stealing machine and one of the best hitters in the league. Just to give you an idea during his first 9 years in Tampa, Crawford stole a combined 409 bases and had a combined average of .294. In 2010 he had his best season yet, stealing 60 bases, hitting .307 with 13 triples, 19 homeruns and had 90 runs batted in while making the AL All-Star team, winning a God Glove award, Silver Slugger award and coming in 7th place for AL MVP voting. Yeah Crawford was a beast in 2010. He became a free agent after that season and signed a huge contract with the Red Sox for 7 years and $142 million. So how did he do? His first 12 games were a nightmare where he only batted .187 with 2 stolen bases and the rest of the 2011 season wasn’t at all any better. Crawford finished the season with a .255 batting average with only 18 stolen bases and an on base percentage of .289. Those are pretty low numbers for a guy who last season was in 7th place in MVP voting and now he is playing like a below average batter. 2012 wasn’t any better as he missed a good portion of the year due to a wrist surgery back in January and also having elbow issues. He was then traded to the Los Angeles Dodgers in August 25th, 2012 including his huge contract that was transferred to the Dodgers organization. He kind of bounced back in L.A but not like how he was back in his first 9 years in Tampa. Crawford said in an interview that his time in Boston was toxic due to the organization and the fans themselves. It caused him to go into a depression and that maybe explains his poor numbers but even so to still play less than how you used to play after leaving a toxic environment kind of shows that his time on top was over the minute he signed his name on that contract. Carl Crawford might had been one of the best forgotten players of all time but his time in Boston and his ridiculous contract will go down in history as one of the worst signings in MLB’s history and Red Sox history. https://www.youtube.com/watch?v=VmddGcA2zkw&t=147s
6. Jason Bay (December 2009, 4 Years, $66 Million with the New York Mets) – This might be the most hated name in the city of Queens and Mets fans as many New York Mets fans consider Jason Bay the worst contract signing of all time. Jason Bay was at one point one of the best power hitters in the league and he is a former NL Rookie of the Year back in 2004. He had his best season in 2009 with the Red Sox hitting 36 homeruns with 119 runs batted in and came in 7th place in MVP voting. He declined arbitration with the Red Sox and became a free agent. The New York Mets swept him up not with a huge contract, only 4 years and $66 million dollars. At the time Bay was on course of becoming a future star not only on the team but in baseball as he was in the prime of his career and was one of the top players in the league. But as we can see it didn’t go so well, in fact it went the opposite direction. Jason Bay’s first season in the Big Apple was a disaster. During a game against the Dodgers Jason Bay collided with the outfield wall while attempting to make a catch. While he did catch the baseball, his head connected with the fenced wall and he was unable to get up on his own as Bay suffered a concussion. He would only play 95 games in his first year on the team due to the concussion but the concussion would play a key role in the rest of his career. From 2011 – 2013 Bay would constantly go onto the disabled list and play poorly and the Mets decided to terminate his contract on his final year. Jason Bay’s career went from becoming one of the best clutch bats to one of the worse players on the field. I kind of take the multiple concussions and injuries on the field as the blame but the poor guy just couldn’t stay healthy. He played one final year with the Seattle Mariners and retired after the 2014 season. The Jason Bay/Mets contract might be the worst yet in the franchise’s history but hey I mean at least they still aren’t paying him until 2039 like they are with Bobby Bonilla. https://www.youtube.com/watch?v=3UkcTSYM8NU
5. Josh Hamilton (December 2012, 5 Years, $125 Million with the Los Angeles Angels) – The Angels the last decade have made some big contract signings. From Albert Pujols’ huge 10 year, $254 million contract to the 10 year, $425 million contract to Mike Trout. Yeah Angels like to spend money but yet they can’t seem to make it into the playoffs. Well the 2012 offseason came and a certain big name was on the market and on December 13th, 2012, Josh Hamilton and the Angels made a huge deal, not like Pujols and Trout but still pretty huge. Josh Hamilton was at the time one of the top names in baseball and one of the most feared hitters. If you saw my Top 10 most overrated MLB Players of All Time list then you know I had the 2010 AL MVP on that list as Hamilton’s career is a rollercoaster ride, on and off the field. But the Angels decided to sign him anyway to a big deal because they thought he could help them lead the way into the World Series. That 2013 Angels lineup looked pretty scary with 3 time MVP Albert Pujols, former Rookie of the Year and future 3 time MVP Mike Trout and 3 times suspended because of drug use Josh Hamilton. Okay all jokes aside Hamilton wasn’t terrible, but he wasn’t worth $125 million considering he is injured prone and a liability with all the problems he has had off the field. So let’s see how he did. Hamilton who hit .285 and 43 homeruns the season prior would only hit 21 homeruns and .250 in his first full season on the team. Okay so it was a bad season for the Angels that year anyway, maybe 2014 will be better. In 2014 Hamilton only played 89 games and hit 10 home runs with a .263 batting average. So what did the Angels do to maybe fix the problems Hamilton was having? They traded his ass back down to Texas for cash. Not only was this a bad singing but this goes to show you that Hamilton was overrated as hell. A man who signed for 5 years and $125 million only stayed 2 years and did nothing to help the team. Not a shocker to me that he is on this list but it goes to show you why the Angels can’t afford any big names not named Mike Trout. https://www.youtube.com/watch?v=XVjxTyw-Krw
4. Pablo Sandoval (November 2014, 5 Years, $90 Million with the Boston Red Sox) – So after the first two signings on this list that went downhill you should know by now Red Sox have made some bad signings in the course of the last 20 years. Pablo Sandoval was never a big time hitter. He was average and came up clutch when his team needed a big hit. He was a fan favorite in San Francisco and he was so loved that he was given the nickname “Kung Fu Panda” because of his speed on the bases, power with the bat and his figure. He also helped the Giants win 3 World Series rings including in 2012 where he won the World Series MVP. Pablo Sandoval was a key name to have in any lineup and the Red Sox decided to take this key and send it over for 5 years for $90 million, which also included a 6th year option worth $17 million, meaning if he stayed on the team he would had made a grand total of $107 million. Like I said Sandoval was an average player and he wasn’t going to have numbers like the best players in the league like Mike Trout or anyone else that played very well during that time. The 2015 season began and as expected it wasn’t a good season for the Panda. Pablo played poorly as his defense was bad, he swung and missed a lot and he only hit .245 with an on base percentage below .300 and he only hit 10 homeruns. 2016 came and Boston decided to bench Sandoval because he was becoming overweight. And that might be the smartest decision because Sandoval got injured early on in the season and required surgery that sidelined him for the remainder of the 2016 season. 2 years and he only played 129 games in 2 seasons and he is making a lot of money for playing like shit. 2017 came and shocking Sandoval was doing poorly again. He only batted .212 with the team before they designated him for an assignment and ultimately released him on July 19th. Sandoval signed back with the Giants but man what a terrible 3 years for a guy who was so loved in baseball and then just hated during his time with the Red Sox. Sandoval remained with the Giants for the next couple of years before being released by the team in 2020 as the player he used to be was gone. Now I don’t think you can blame Sandoval fully as this happens to many players who go from playing in the National League to the American League plus Boston’s environment isn’t the healthiest. But at the same time Sandoval had a choice to be healthy with his own weight and instead he let himself go and his career went south. It’s pretty sad when you think about it but what can you do. https://www.youtube.com/watch?v=JLdxjNiNmzE
3. Homer Bailey (February 2014, 6 Years, $105 Million with the Cincinnati Reds) - The career of the lookalike of Christian Bale is very confusing as Homer Bailey is only 34 years old and feels like he has been in the league for almost 20 years and yet he made his debut in 2007. Bailey’s career is also a rollercoaster ride as he isn’t an ace pitcher but somehow managed to throw two no hitters. Homer Bailey was at one point one of the top prospects in the MLB and let’s just say that this might be a typo. Homer Bailey has only a handful of winning seasons on his belt and by the time of this contract he was only 27 years old and entering his 8th year with the Reds. The Reds re-signed Bailey for 6 years as he was coming off 3 straight decent seasons and they were looking to make him their top ace pitcher in the starting rotation. He signed for a 6 year contract worth $105 million and at the time of the contract he was the 3rd highest paid player on the team, only behind Brandon Phillips and Joey Votto. His first year under his new contract he did pretty well but was diagnosed with arm fatigue, ending his season early with only 23 games pitched and having a 9-5 record with an ERA of 3.71. Not a bad year for someone who missed the final month and a half of the season but this now leads us to why this was a bad contract signing. Homer Bailey the next season only played 2 games as it was announced that not only was he having arm fatigue, but he also needed to get Tommy John surgery. He missed most of the 2016 season as well and only pitched in 6 games. His 2017 season started on the disabled list as well and he missed a good month and a half. Once he did return he wasn’t any good. His ERA that season was 6.43 and then in 2018 he had an even worse year where he went 1-14 with an ERA just above 6. He pitched so bad that the Reds took him off the starting rotation. Now of the last 4 years prior to his decent 2014 season, Homer Bailey was the 2nd highest paid Cincinnati Red, behind Joey Votto. It’s pretty sad that pretty much your 2nd highest paid player that you are giving 10 million – almost 20 million a year in those 6 years can’t pitch because of injuries or when he is healthy he pretty much is pitching terribly. From 2015 – 2018 his combined ERA is 6.18 and he was being paid again 10 – 20 million a year to be there ace pitcher. Bailey had potential to be the top pitcher on the Reds but injuries and poor playing really plagued Bailey’s 2nd half of his years with Cincinnati. Had he stayed healthy we could have seen an ace pitcher. It’s a shame really as he was beginning to become a top pitcher before he signed that huge contract, but once the name was signed on the dotted line his career took a big turn for the worse and went downhill. https://www.youtube.com/watch?v=kOqnP-fb-0M
2. Mike Hampton (December 2000, 8 Years, $121 Million with the Colorado Rockies) – Prior to this signing Mike Hampton was making a name for himself. His first few seasons were back and forth but he showed true potential of being an ace starting pitcher and in 1999 at the age of 26, Mike Hampton had an amazing season with a Win/Loss record of 22-4 with a 2.90 ERA and came in 2nd place for Cy Young. The next season he was traded to the Mets and pitched pretty well. He became a free agent after his one year stint with the Mets and found himself with a huge contract with the Colorado Rockies, a deal worth $121 million for 8 years. Hampton at the time had the largest contact in all of MLB and was literally the talk of the town since he was considered one of the best starting pitchers of the last few years and well apparently he forgot how to pitch like an ace because Hampton struggled big time. Hampton was hitting pretty well as a pitcher and won a couple of Silver Sluggers during his time with the Rockies but he was having command problems with his pitching and was giving up a lot of hits and runs. His first two seasons while under contract he had a combine 21-25 record with an average ERA of 5.78. He also gave up a combined 464 hits and 273 runs in a combined 381.2 innings pitched. Talk about a terrible signing and the fact that this guy was the highest paid player at the time and pitching so terrible makes this one of the worst signings ever. But then after his 2nd season with the Rockies, he was traded to the Marlins and Braves in one month. Hampton would pitch pretty decent in Atlanta but the damage was already done and he was seen as a different pitcher. He was no longer an ace but maybe a 4th or 5th starting pitcher in the rotation. It’s a shame on how Hampton career took a downward spiral in Colorado as he was once one of the best pitchers in the league.
1. Chris Davis (January 2016, 7 Years, $161 Million with the Baltimore Orioles) – I mean giving $161 million to one of the most overrated players at the time of the deal proves why this is the worst signing ever. Chris Davis prior to this deal was never a great player but his biggest thing he was known for was hitting dingers. Early on in his Orioles career, Davis hit 53 homeruns and came in 3rd place in the MVP voting but since that season he struggled to get on base and always had a low betting average while striking out a lot. The one thing he was still doing was crushing baseballs over the outfield walls. So when the 2016 season was coming, the Orioles wanted to keep their top slugger, even though he struggled to get on base and hit a batting average above .270. So they did what any dumb team would do, they re-signed him to a huge 7 year contract worth $161 million. I guess you can say what happened next as his career went downhill after this deal. He hit 38 dingers in his first year back with the team but once again struggled with hitting and getting on base. The next few seasons he then struggled to do the one reason why the Orioles signed him for over $160 million, he struggled to hit dingers. His power was decreasing each season and so was his ability to hit a baseball. In fact in the 2019 season he started it with being hitless in 54 consecutive at bats. He barely played in the 2020 season due to a knee injury but I mean the damage has already been done as Davis career became a huge joke. Think about this Davis is pretty much making $23 million a season and he is being paid over $20 million to play terribly and be the worst baseball player in the league. This isn’t just a terrible contract for the Orioles, this is the worst contract ever in baseball history. There is a reason why Baltimore can’t afford big names in the free agency because most of the salary is going towards Davis to pretty much participate. https://www.youtube.com/watch?v=zurwRZXeEfw&t=550s
Honorable Mentions:
Kei Igawa (5 Years, $20 Million with the New York Yankees) – This was a signing that included a $26 million bid for the Japanese starting pitcher. While under contract with the Yankees, Kei Igawa was terrible. In his first start alone he gave up 7 earned runs and it never got better over time. He mostly played in the minor leagues and was released in 2011. He only played a handful of games in the major leagues and had a 2-4 record with a 6.66 ERA.
Rusney Castillo (7 Years, $72.5 Million with the Red Sox) – Rusney Castillo is another international signing gone bad as he barely played in the major leagues with the Red Sox. In just 7 years of his contract he played 99 games in the major leagues and barely did anything memorable for the Red Sox.
Mo Vaughn (6 Years, $80 Million with the Anaheim Angels) – This signing is on here for unfortunate reasons as Mo Vaughn was actually playing really well with the Angels but a big injury and a weight problem plagued Vaughn’s career with the Angels in the 3rd year of his contract. He was traded in the final days of 2001 and his career took a downward spiral.
Carl Pavano (4 Years, $39.5 Million with the New York Yankees) – 2004 was Pavano’s best season. He finished in 6th place for the NL Cy Young and had a 18 – 8 record with a 3.00 ERA. Prior to this Pavano wasn’t seen as a big name pitcher but heading into the 2004 offseason he was seen as a possible big signing. He signed with the Yankees for 4 years and in those 4 years Pavano couldn’t stay healthy and pitched terribly. To think he only pitched 26 MLB games in those 4 years and was getting paid pretty much $40 million to sit on the disabled list.
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