15 worst Toronto Blue Jays free agent signings in franchise history

15. RHP Clay Buchholz - one year, $3M (2018-2019 offseason)

A longtime member of the rival Boston Red Sox, Buchholz came aboard the Blue Jays organization at the tail end of what had been a storied career.

After throwing a stunning no-hitter in just his second big league start, Buchholz went on to be a highly respectable member of the Sox’s rotation, going 81-61 with a 109 ERA+ in parts of 10 years. He made two All-Star Games and was a part of the 2013 World Series winning club.

After struggling mightily with the Phillies in 2017, he signed on with the Diamondbacks and did exceptionally well. In 16 starts for the 2018 D’backs, he went 7-2 with a sparkling 2.01 ERA and 209 ERA+.

This performance warranted a contract from the Blue Jays, but the deal blew up in the club’s face. In 12 starts for the 2019 Jays, Buchholz posted a 6.56 ERA, allowing 11.0 H/9 and seeing a dramatic dropoff in essentially every single relevant pitching statistic.

Buchholz represents the first of many on this list who failed to put it together as a member of the Blue Jays. Unfortunately, it only gets worse from here.

14. OF Mookie Wilson - two years, $2.75M (1989-1990 offseason)

Wilson was initially acquired via trade from the New York Mets, but he elected free agency at the end of the 1989 season. Exactly two weeks later, he had re-upped with the Blue Jays on a two-year contract.

He began his career with the Mets and was a very exciting player in the early days. A switch-hitter, Wilson possessed an impressive ability to hit for some pop, steal a ton of bases and play solid defense in the outfield.

As he aged, all three of those characteristics began to decline rather quickly. By the time he became a member of the Jays, he had no pop left, was stealing less bases, his defensive metrics were poor and his awful eye at the plate became even more exposed than it had been in year’s past.

In 1989 alone, he played in just 54 games for Toronto but struck out 37 times and walked … only three times.

In 1990, his first (and ultimately, only) full season with the Jays, he hit just three home runs in 147 games and posted a .241 average and a 70 OPS+. He saw a minor uptick in both his oWAR and dWAR but overall was not a productive player.

Wilson wound up losing the starting center field job to Devon White in 1991 and didn’t produce at all in an 86-game showing in what was his last season in the majors.

13. RHP Pat Hengten - one year, $2.2M (2003-2004 offseason)

While everyone loves a good reunion story, this one was never meant to be.

Hentgen, one of the earliest true “aces” the Blue Jays had, began his career in Toronto and emerged as one of the most dynamic starting pitchers in the league. In 1993 he broke out, going 19-9 and making his first career All-Star Game. He finished sixth in the AL Cy Young Award voting that year.

He made another ASG appearance in 1994 and then went off in 1996, going 20-10 with a 3.22 ERA and 156 ERA+. He threw 10 complete games and three complete game shutouts and led the American League with a 0.7 HR/9 rate. This was enough for him to win the Cy Young Award that season. 

Hentgen followed up his award-winning performance with his fourth and final All-Star Game appearance. After that 1997 season, he began to slowly decline and eventually made appearances for the St. Louis Cardinals and Baltimore Orioles before coming back to Toronto.

At the age of 35, Hentgen returned to the Jays and looked … awful. In 18 appearances (16 starts), he went 2-9 with a 6.95 ERA and 6.53 FIP. He walked (42) more than he struck out (33) and just looked lost on the mound. This was the last he was seen at the big league level, but he retired as one of the best pitchers to ever wear a Blue Jays uniform thanks to what he did in his first go-round.

12. OF Otis Nixon - two years, $4.4M (1995-1996 offseason)

Prior to his brief career as a member of the Toronto Blue Jays, Nixon had functioned as a pesky leadoff hitter who had some serious wheels for multiple clubs including the Yankees, Indians, Expos, Braves, Red Sox and Rangers.

He was a lock for over 50 stolen bases a year while hitting somewhere in the .270-.290 range and was good for some solid defense in the center field, his position by trade.

Nixon was essentially JUST a singles hitter. He had zero pop whatsoever and didn’t ever post much in the way of extra base hits throughout his career. In 1991, he had 119 hits and only 11 of them were for extra bases.

With the Jays, his contract didn’t necessarily break the bank, but it also provided little in the way of actual value. He had an OPS+ of just 78 over the course of his two year tenure in Toronto and saw his defensive value completely disappear. In 228 games he posted a combined -0.6 dWAR for the club.

Nixon was a slap-hitting switch-hitter who served a clear purpose for teams over the years. The Jays got him at the tail end of his career and ultimately didn’t get much.

11. RHP Erik Hanson - three years, $9.4M (1995-1996 offseason)

After breaking into the league as a 23-year-old back in 1988, Hanson was actually a pretty dang good pitcher for the first seven or so years of his career. 

As a member of the Seattle Mariners, he made 145 appearances with a respectable 3.69 ERA and 111 ERA+. He was always a pitcher who didn’t rely too heavily on the strikeout (although he did rack up 211 Ks in 1990) and did an exceptional job at limiting walks and home runs.

After leaving the Mariners six years into his big league career, he spent the 1994 season with the Reds and 1995 with the Red Sox, making his first (and only) All-Star Game appearance.

Hanson hit free agency at the conclusion of the 1995 season and he had many suitors on the open market. The Toronto Blue Jays won the sweepstakes, signing him to a three-year deal that would guarantee him just under $10M.

In his first season with the Blue Jays, the wheels completely fell off. He went 13-17 with a 5.41 ERA in 35 starts. He allowed over 10 hits per nine innings, walked over 100 batters and managed an ERA+ of just 93. 

The injury bug bit Hanson in both 1997 and 1998 and he was able to make a combined 14 appearances. His career in Toronto wound up being a total dud, as he was worth just 1.3 bWAR and had an overall ERA+ of 87.

10. LHP Ken Dayley - three years, $6.3M (1990-1991 offseason)

While Dayley was guaranteed less money than Hanson was, his deal easily wound up being worse for the Jays. 

Like Hanson, Dayley had experienced a full career of success before coming north of the border to play for his first American League team. Before coming to Toronto, Dayley functioned as an oft-used middle reliever for the Cardinals and Braves.

He was consistently a lock to have an ERA in the low-3.00s and was one of the best around when it came to limiting the longball.

At 32-years-old, Dayley signed with the Blue Jays on a three-year deal that completely blew up in the face of the club. He was limited to just 10 appearances in those three seasons, eight in 1991 and two in 1993.

Dayley suffered from an intense bout of vertigo that was the largest culprit in his missing so much time. When he did make it onto the mound, he struggled, posting a 6.23 ERA in 1991 while walking (5) more than he struck out (3).

He was not a bad player but this deal turned out to be awful for the Jays.

9. RHP Matt Shoemaker - two years, $7.7M (2018-2019 offseason)

Shoemaker technically signed just a one-year deal with the Jays heading into the 2019 season, but his full contract wound up becoming much worse thanks to arbitration.

Coming off of a successful but injury-plagued stretch with the Angels, Shoemaker was a highly sought-after starter who had shown in the past that when he’s healthy, he can be a very solid pitcher.

The former AL Rookie of the Year runner up made just five starts for the club in 2019 but they were extremely encouraging ones. Across 28+ innings, he posted a miniscule 1.57 ERA and 29 ERA+, striking out 24 batters and walking just nine.

Shoemaker went down with a torn ACL and spent the remainder of that season on the injured list. 

Despite the fact that he was injured, Shoemaker earned a raise through the arbitration process, seeing his salary go from $3.5M to $4.2M in the following season.

When he was finally able to return to a big league mound, the then-33-year-old looked to be a shell of himself. He made six starts this time, posting a 4.71 ERA and ghastly 5.95 FIP in 28+ innings. He surrendered home runs at an alarming rate in what ultimately wound up being the last we saw of him in a Jays uniform.

Shoemaker’s start to his Blue Jays career was filled with so much promise. Once all was said and done, he was paid $7.7M by a club that only saw him take the mound 11 times.

8. INF Maicer Izturis - three years, $9M (2012-2013 offseason)

What a strange contract this was. After playing for the Expos and Angels for the first eight years of his big league career, Izturis signed a three-year contract (plus a fourth option year) with the Blue Jays heading into his age 32 season.

A light-hitting switch-hitter who had a reputation for being a poor hitter but strong defender, Izturis wasn’t even able to continue this trend for his new club. He didn’t hit, he didn’t field and he didn’t even play out the entirety of his contract.

In 2013, Izturis played just 107 games before going down with an injury that took him out of play in the second half. He had hit just .238 with a 65 OPS+, good for -0.1 oWAR. His defense was worse, as Baseball Reference says he was worth -0.3 dWAR in this abbreviated season.

2014 was another wasted season as the middle infielder made just 11 appearances before, you guessed it, going down with an injury that took him out for the remainder of the year. 

Entering 2015, what was going to be the last year on his deal no matter what, Izturis was finally healthy. Until he wasn’t. This time he didn’t even make it out of Spring Training.

He opened the regular season on the injured list and ultimately underwent yet another surgery in June and did not play a single game for the Jays that year. His option was declined at the end of the season and he wound up retiring from the game that offseason despite the fact that he re-signed with the Jays on a minor league deal.

While Izturis was awful during his tenure, he wasn’t making a ton of money, which makes it easier to place him so far down on this list.

7. DH Kendrys Morales - three years, $33M (2016-2017 offseason)

If it weren’t for two decent seasons at the plate, Morales would’ve found himself much higher on the list. He didn’t play out the entirety of the contract but performed admirably enough to warrant being lower on the list.

Morales had been an underrated player throughout his career. He was one heck of a power hitter and had little trouble being a productive big leaguer, it was just his health that was the biggest issue.

After a successful six-tenure as a member of the Angels, Morales spent time with the Twins, Mariners and World Series-winning Royals before signing a three-year, $33M contract with the Jays.

Respect to the Jays for making a “going for it” signing like this, but overall, this contract ended up being a bad one for the club. 

Morales wound up playing in just two of the three years on his deal. He hit over 20 home runs and was at or above a 100 OPS+ but his contract quickly became an albatross and he was flipped to the Oakland A’s for next to nothing. 

After the trade, horribly underperformed with both the A’s and Yankees before retiring at the conclusion of the 2019 season.

6. 3B Corey Koskie - three years, $17M (2004-2005 offseason)

Koskie joined the Blue Jays as a 32-year-old corner infielder with seven years of big league experience under his belt. He didn’t make any All-Star Games and wasn’t ever viewed as one of the premier hitters in the game, but he quietly went about his business and posted a combined 116 OPS+ with the Twins.

A power-hitting, sleek defender at third base, Koskie signed a fairly significant contract by the Jays standards heading into the 2005 season. His addition to the club was viewed as a “going for it” type of move just as Morales’ was.

Out of 486 possible games over the next three years, Koskie played 97 contests for the Jays, all coming in 2005. After an injury-plagued season, he was traded away just one year into his contract.

This deal just never worked out for the Jays. The club’s biggest move in the 2004 offseason was quickly viewed as expendable with multiple other third base options in the organization like Eric Hinske, Troy Glaus and Shea Hillenbrand. He was moved to the Milwaukee Brewers and made just 76 appearances for them before retiring due to post-concussion syndrome.

5. LHP Jaime García - one year, $8M (2017-2018 offseason)

García, a longtime member of the St. Louis Cardinals, came over to the Blue Jays at what ultimately was the end of his big league career. When he was healthy, he was one of the better left-handed pitchers in the game, but that was exactly this problem. He was never healthy.

After his eight-year tenure with the Cardinals, García played for three teams in 2017, the Braves, Yankees and Twins. He made 27 starts but his strikeouts were down and his 4.41 ERA and 4.25 FIP were not where he had been in previous years.

The Blue Jays signed him to a one year, $8M contract heading into the 2018 season in hopes of capturing lightning in a bottle and seeing him return to his 2010-2012 and 2015 form. 

There’s no way to describe García’s tenure in Toronto other than saying he stunk up the joint. His Jays debut was excellent: six innings, one run, seven strikeouts. Essentially every outing after that was a downhill descent for him.

As he fought through injuries all year long, García limped to a 5.93 ERA and 72 ERA+ in 74 innings for the Jays, making 25 total appearances with just 13 of them being starts. He struggled mightily to keep the ball in the ballpark and was an overall eyesore for the Jays and their rotation.

He wasn’t even able to make it through the full season. Released in August, García latched on with the Cubs and struggled there as well before retiring at the end of the season.

4. DH Frank Thomas - two years, $18M (2006-2007 offseason)

It’s understandable why the Blue Jays were interested in a slugger like Frank Thomas. “The Big Hurt” was one of the most fearsome sluggers of his time and was well on his way to the MLB Hall of Fame once he hung it up.

However, this contract was such a massive overpay, it’s a wonder why anyone thought it was a good idea to sign a 39-year-old to such a significant contract. Two years was a lot to begin with, but the amount of money Thomas was to be paid is what made it ridiculous.

Thomas’ first year in Toronto went well. He played in 155 games (his highest in seven years) and hit 30 doubles, 26 home runs and drove in 95 runs. His 125 OPS+ was the second-highest on the 2007 Jays behind Matt Stairs.

In 2008 at the age of 40, the wheels completely fell off for the player who once had can’t-miss at-bats. Making roughly $12.5M on the year, Thomas completely imploded at the plate, making it through just 16 games and 72 plate appearances before seeing his playing time begin to dwindle.

After hitting just .167 with a 72 OPS+, Thomas was benched and immediately went running to the press to express his distaste with the decision made by Blue Jays management.

Shortly after his outburst, the Blue Jays made the decision to release him from the team. 

Even though his first season in Toronto went well, it’s easy to label this signing as a dud. Thomas melted down in his second season and was paid entirely too much money for someone as old as he was.

3. OF José Bautista - one year, $18M (2016-2017 offseason)

This was a tough decision. Bautista is one of the most prolific power hitters to ever suit up for the Blue Jays. His stretch of play from 2010-2016 will live on in the hearts of Jays Nation forever, and rightfully so.

After becoming a free agent at the end of the 2016 campaign, Bautista had a chance to hit the open market and potentially leave Toronto, the city where he rose to stardom.

However, he re-signed with the Jays in January of 2017 after declining the $17.2M qualifying offer extended by the club.

It was immediately clear that this was not the Joey Bats of years past. He played 157 games for the club (his highest since 2010), but struggled mightily at the plate. This was an unwelcome development for Jays fans, as he had not performed this poorly since a 21-game cameo in 2008.

Bautista still hit 27 doubles and 23 home runs, but he just barely stayed above the Mendoza Line with his .203 batting average and had an OPS+ of just 79, meaning he was 21 percent worse than league-average. His -1.0 bWAR was easily the lowest he had put up since all the way back in 2006 as a member of the Pittsburgh Pirates.

The reason this contract isn’t ranked even higher is because of the fact that the 2017 Blue Jays were never meant to be winners. After all, this is a club that trotted out Darwin Barney, Ryan Goins, Steve Pearce and Kevin Pillar on a daily basis. The pitching staff consisted of struggling pitchers like Marco Estrada, Francisco Liriano and Joe Biagini.

Bautista deserves every bit of recognition and fame that he gets from his peak years in Toronto. However, this contract was an extreme overpay and he offered next to nothing on the 2017 Jays.

2. RHP Tanner Roark - two years, $24M (2019-2020 offseason)

What makes the Roark contract worse than Bautista’s is the fact that he was brought aboard to help shore up a rotation of a contending club. Signed prior to the COVID-shortened 2020 season, Roark was expected to be a key part of a rotation already consisting of Hyun Jin Ryu, Taijuan Walker, Robbie Ray and Matt Shoemaker.

Before joining the Blue Jays, Roark was a quietly solid pitcher for the Washington Nationals for the first six seasons of his career. He spent 2019 as a member of the Reds and A’s and performed decently there as well.

As a member of the Jays, he just looked lost on the mound and couldn’t find any sort of sustained success to save his life.

For the amount of money the Jays were forking over to him on this contract, he should’ve done better.

In 2020, he made 11 starts and had a dreadful 6.80 ERA and an even more dreadful 6.86 FIP and 65 ERA+. He allowed 14 home runs in just 47 innings and walked 4.3 batters per nine innings, easily the highest mark of his career.

The club was able to make it to the AL Wild Card Series without any help from Roark, but ultimately lost to the Rays in a 2-0 sweep.

In 2021, the Jays were looking to further improve on what was a successful season in 2020. The team won 91 games and saw Robbie Ray win the Cy Young Award, but Roark once again was absolutely no help.

He made just three appearances that year and was shelled on the mound once again. His 6.43 ERA and 8.17 FIP were just awful, despite the fact that it was a small sample size. In seven innings, he allowed five earned runs and surrendered three home runs.

Even though he was making $12M on the season, the Jays released him in May and he never made another appearance at the game’s highest level.

1. LHP B.J. Ryan - five years, $47M (2005-2006 offseason)

Ryan is still one of the most expensive free agent signings the Blue Jays have ever made. He was a very successful reliever for the Orioles in the seven years leading up to his deal with Toronto and had many, many ups and downs with the Jays.

What makes this contract the most frustrating is the fact that he did very well in two of the four years he spent in Toronto. In 2006, Ryan was an All-Star and had a 1.37 ERA in 65 games, earning 38 saves along the way and posting an impressive 0.4 HR/9 rate.

Then in 2007, he made just five appearances before going down with injury. In that time, he had a 12.46 ERA in 4.1 innings, walking four batters and striking out three, no longer showing the impressive control he had shown off in the year prior.

In 2008 with health on his side, Ryan once again excelled for the Jays. He made 60 appearances of 2.95 ERA-ball and earned 32 more saves. Once again, his 0.6 HR/9 was one of the best in the league and he continued to excel at limiting the walk.

Ryan’s contract with Toronto was insanely backloaded, meaning it was cheap in the first two years but the AAV went way up in the last two before he was released. In 2006, he made $4M. In 2007, he made $7M. In 2008 and 2009, he made $12M.

His final year with the Jays came in 2009 and he was a shell of the pitcher he once was. Ryan made 25 appearances and had a 6.53 ERA and 7.60 FIP in 20.2 innings. His control was completely gone and he gave up home runs at an alarming rate.

The Blue Jays had no choice but to release him, in part from the inconsistency he had shown over the years and partly because he was that bad in 2009. At the time of his release, he was still owed the $10M he was guaranteed for the 2010 season.