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Jays Listed: Top 10 Worst Trades

A few weeks ago I went over the Top 10 Best Trades in Blue Jays history, so you had to know the Top 10 worst trades were coming soon. Well, here they are.

Through their 36 years Blue Jays GM’s have made a few boneheaded trades, but thankfully none of them rank up there with Larry Anderson for Jeff Bagwell or Derek Lowe and Jason Varitek for Heathcliff Slocumb.

When going through 36 years worth of trades to pick out the 10 one thing that I found was (unless I missed one) Pat Gillick never made a horrible trade. You will not find a single trade made by Pat Gillick on this list. No wonder the genius is in the Hall of Fame.

Unfortunately for Jays fans the same could not be said for Gord Ash as you will see on the list time and time again. Here we go…


10. 1998 – Ed Sprague traded to the Oakland Athletics for Scott Rivette

Sprague had a few great and a number of mediocre seasons with the Jays, but he had to be worth more on the market than minor leaguer Scott Rivette. Sprague’s best season with Toronto, and best season period, was in 1996 when he hit 36 home runs and drove in 101 runs.

Two years later in 1998 Sprague was hitting .238 with 17 home runs and 51 RBI through 105 game when the Jays sent him to Oakland for Rivette. He scuffled in Oakland with three homers and a lackluster .149 average through 27 games before leaving via free agency to sign with the Pirates. In 1999 he was an All-Star with the Pirates (no offense but being a Pirates All-Star in the late 90′s didn’t mean much) and hit 22 home runs with 81 RBI and hit a career-high .267.

The trade wouldn’t have been too bad if Rivette had done something. Rivette never pitched in the Majors topping out at AA with the Jays. He finished off his career in the Seattle Minor league system in 2000.


9. 1998 – Blue Jays traded Mike Stanley to the Boston Red Sox for Jay Yennaco and Peter Munro.

This was the first trade ever made between the Blue Jays and Red Sox. If it hadn’t happened the 1998 season might have ended a little differently. The Blue Jays sent Stanley to the Red Sox on July 30, 1998 near the deadline. Toronto made a few other deadline moves that season, parting with Juan Guzman, Tony Phillips and Ed Sprague as well.

After arriving in Boston, Stanely’s bat, which has been solid in Toronto, caught fire. With Boston Stanley hit .288 with seven home runs and 32 RBI in 47 games. With Stanley’s help the Red Sox won the Wild Card, while the Jays, despite being gutted at the trade deadline, finished only four games back.

Would the Jays have been able to make up those four games with Stanley’s bat in the Jays lineup instead of the Red Sox?


8. 2011 – Blue Jays traded Mike Napoli to the Texas Rangers for Frank Francisco

Mike Napoli never played a game for the Jays after Alex Anthopoulos duped the Angels into taking Vernon Wells and his fat contract for Napoli and Juan Rivera. As great as the trade was on the Toronto payroll in hind sight AA probably should have gotten more for Napoli when he flipped him to Texas four days later.

With J.P. Arencibia coming up and Travis D’Arnaud on the farm the Jays appeared to have behind the plate covered for awhile, so getting Napoli in the Wells deal only made sense if he was on his way out the door not long after he came through it. In his final season with the Angels Napoli actually played more at first base than he did behind the plate. A big part of that was likely due to Kendrys Morales season-ending broken leg.

During that season he appeared in a career-high 140 games and hit .238 with 26 home runs and 68 RBI. Who could have a guessed that the following season with Texas he would blow those numbers out of the water in 27 fewer games? In his first season with the Rangers Napoli hit .320 with 30 home runs, 75 RBI and a 1.046 OPS, all career highs. Napoli also posted a 5.2 WAR

Francisco was acquired to be the Jays closer for the 2011 season, but ended up starting the season on the DL. When he did make his Blue Jays debut he gave up a home run to Curtis Granderson on his very first pitch. He finished the season with 17 saves, four blown saves and a 1-4 record. He did finish the year on a high note successfully converting his last seven save chances, but Toronto still decided to let him leave via free agency following the season. One year shaky closing seems a little cheap for Mike Napoli now.


7. 2003 Blue Jays traded Shannon Stewart and Dave Gassner for Bobby Kielty

This trade turned out all right for the Jays in the end as they were able to spin Kielty to Oakland a year later for Ted Lilly, but is that really all they could get for Stewart near the trade deadline in 2003?

In the season before being traded Stewart hit .303 with a .371 OBP, 10 home runs, 14 steals and 103 runs scored. He also had a WAR of 3.0. At the time of the trade in 2003 Stewart was hitting 294 with a .347 OBP, seven home runs and 47 runs scored through 71 games. By comparison, at the time of the trade Kielty was hitting .244 with a .358 OBP, with 12 home runs in 112 games for the Twins.

Following the trade Stewart was an immediate spark for the Twins. In 65 games with Minnesota Stewart batted .322 and clubbed six home runs. He also scored 43 runs and and had 38 RBI. Stewart’s red-hot bat down the stretch for the Twins helped them win 12 of their last 15 games to capture the AL Central and helped him to finish fourth in MVP voting that season.

During the same time in Toronto Kielty played in 62 games for the Jays and hit .233. He only hit four home runs and had 25 RBI. His WAR with the Jays in 2002 was -0.2. Stewart’s WAR with the Twins at the same time was 2.5. Looking at the numbers for Stewart and Kielty before and after the trade it looks like the Twins majorly ripped off the Jays with this deal.


6.1996 – Blue Jays traded John Olerud to the New York Mets for Robert Person

With Carlos Delgado ready to takeover first base John Olerud was expendable following the 1996 season. The trade itself was a good move that way, but was Robert Person really all Toronto could get for Olerud?

The 1996 season likely didn’t bolster Olerud’s trade value. The former batting champion hit only .274 with 18 home runs and 61 RBI in 125 games. Those numbers immediately sky rocketed with the Mets. In his first season in New York Olerud’s average climbed to .294 and he clubbed 22 home runs while driving in 102 runs. The following season he was even better setting a Mets’ record with a .354 average and a .447 OBP.

While Olerud flourished with the Mets, Person floundered with the Jays. He was placed in the starting rotation in his first season in Toronto but struggled to find consistency while posting a 5-10 record, a 5.61 ERA and a 1.44 WHIP. The following season he was moved to the bullpen and spent some time as the closer.

The bullpen didn’t bring the best out in Person though as his ERA climbed to 7.04 and his WHIP was an ugly 1.748. In 1999 he appeared in 11 games for the Jays still getting clobbered to the tune of a 9.82 ERA and a 2.18 WHIP before Toronto traded him to Philadelphia for Paul Spoljaric.

Control was a big problem for Person while with the Jays, as he averaged nearly five walks per nine innings and he was also plagued by the home run, having given up 29 home runs in only 177.2 innings. Not surprisingly Person’s WAR while with the Jays was -1.9


5. 2000 – Blue Jays traded Darwin Cubillan and Michael Young for Esteban Loaiza

How could the Jays let Darwin Cubillan go? Seriously though, this trade hurts because of what became of Michael Young. Where do we start with Young? Well, the Jays drafted him in the fifth round in 1997. Since arriving in Texas Young has been a seven-time All-Star and a gold glove winner who has played every position around the infield. Young has hit over .300 seven times and topped the 20-home run mark four times. Instead of Michael Young at shortstop or third base for the last decade the Blue Jays had guys like Chris Woodward, Russ Adams, Royce Clayton and David Eckstein.

In case you’re wondering about Darwin Cubillan he only appeared in 13 games for the Rangers, all out of the bullpen in 2000. In those 13 games he had a 10.70 ERA after giving up 21 earned runs on only 17 2-3 innings.

Esteban Loazia spent three mediocre seasons in Toronto, compiling a 25-28 record with a 4.96 ERA and a 1.45 WHIP. His WAR over those three years was only 3.1, of which 2.2 came in one season in 2000. That 2000 season was arguably his best in Toronto when despite a 3.62 ERA and a 1.31 WHIP he had a losing record at 5-7. Who needs Michael Young when you get that kind of production from the rotation?


4. 1996 – Blue Jays traded Brandon Cromer, Jose Pett, Jose Silva, Mike Halperin, Abraham Nunez and Craig Wilson for Orlando Merced, Carlos Garcia and Dan Plesac

This nine-player deal was supposed to be a big part in the Jays resurgence during the 1997 season by netting them a former Rookie of the Year runner-up in Orlando Merced and a former All-Star in Carlos Garcia. Also during that offseason the Jays signed Roger Clemens and Benito Santiago and changed the team’s logo for the first time. The end result? A Cy Young for Clemens but a 76-86 record and a last place finish for the Jays.

But anyway, back to the trade. Let’s start with Orlando Merced. In his last season with the Pirates before the trade Merced had hit .287 with a career-high 17 home runs and 80 RBI. Those numbers did not follow him to Toronto. In his only season with the Jays injuries limited Merced to only 98 games. He hit .266 with nine homers and 40 RBI, but he did have a better than expected WAR at 2.3

The way they hyped Carlos Garcia following the trade he never had a chance to live up to his billing with the Jays. Some daft reporters actually said Toronto has finally found a suitable replacement for Roberto Alomar at second base. Boy, were they wrong. With the Pirates Garcia was an All-Star in 1994 and had his best season in ’95 when he hit .294 and drove in 50 runs in 104 games. In Toronto his bat went cold and he hit a lousy .220 with 23 RBI and only 29 runs scored in 103 games. He also posted a -2.3 WAR, the worst in Jays history by a position player.

Oddly enough the best player the Jays acquired in the trade was Dan Plesac, who was considered a throw-in at the time. Plesac ended up being a reliable left-handed specialist out of the Jays bullpen recording a strikeout rate of 10.9 per nine innings in his first season in Toronto. He was traded to Arizona in 1999 for Tony Batista and returned to Toronto as a free agent a few years later in 2002.

The Pirates received six prospects in the deal that weakened the Jays minor league stockpile, but only two of them really made any impact for Pittsburgh. Abraham Nunez played eight seasons in Pittsburgh mostly at short stop, third base or off the bench. He was never a star, hitting .238 with 11 home runs and 117 RBI while with the Pirates.

The best acquisition for Pittsburgh in the deal was Craig Wilson. He spent six seasons with the Pirates, batting .268 with 94 home runs and 282 RBI. His best season was in 2004 when he played in a career-high 155 games and hit .264 with 29 home runs, 82 RBI and a 3.6 WAR.

The Jays may not have lost much overall to the Pirates in the deal, but what they received in return was so underwhelming it became another black spot on Gord Ash’s Toronto resume.


3. 1998 – Blue Jays traded Woody Williams, Carlos Almanzar and Peter Tucci to the San Diego Padres for Joey Hamilton

What a disaster this trade turned out to be. In five seasons with the Padres Hamilton posted a 55-44 record with a 3.83 ERA so it looked like the Jays were getting a solid No. 3 starter. That turned out to be far from the case. Hamilton actually started his Toronto career at AAA with Syracuse. After getting the call from the big club in his first season with the Jays Hamilton went 7-8 with a 6.52 ERA.

The 2000 season was a complete wash for Hamilton who spent most of the year on the DL. He started only six games, posting a 2-1 record with a 3.55 ERA. Things didn’t get any better in 2001 as Hamilton posted a 5.89 ERA and a 5-8 record in 22 starts before being released on August 3. In parts of three seasons with the Jays Hamilton posted a 14-17 record with a 5.83 ERA and an ugly 1.59 WHIP. His WAR while with Toronto was a miserable -0.4.

Making things even worse for the Jays, the main part of the deal heading to San Diego, Woody Williams put up much better numbers than Hamilton. In his first season in San Diego Williams went 12-12 with a 4.41 for an awful Padres team that finished dead last in the NL West. He would spend parts of three season with San Diego before another trade saw him get shipped to St. Louis. His numbers with San Diego included a 30-29 record, a 4.35 ERA and a 5.3 WAR. Williams would go on to win a career-high 18 games with the Cardinals in 2003 and he posted an ERA under 3.00 in 2001 and 2002.

The other pieces of the trade Almanzar and Tucci never really panned wherever they ended up. Almanzar had a rough season in the San Diego bullpen in 1999 with a 7.47 ERA and a 1.68 WHIP. His WAR that season was -0.7. He was traded to the Yankees prior to the 2001 season and after a respectable year in the New York bullpen he bounced around numerous clubs making short stops in Colorado, Cincinnati, Texas, Atlanta and Boston.

Peter Tucci never played a game in the Majors and in some ways I’d rather have that than what the Jays got out of Hamilton in his three seasons in Toronto.


2. 1995 – Blue Jays traded David Cone to the New York Yankees for Marty Janzen, Mike Gordon and Jason Jarvis

With the baseball strike finally over the Jays prepared for the 1995 season by acquiring the reigning Cy Young Award winner, David Cone from the Royals on April 6, 1995. Cone’s second stint with the Jays would prove to almost as short as his first in 1992. With the Jays in 1995 Cone started 17 games and posted a 9-6 record with a 3.38 ERA before getting shipped to the Yankees on July 28.

Cone continued to be a dominant starter while with New York. During the rest of the ’95 season he went 9-2 with a 3.82 ERA in 13 starts. In 1996 he only started 11 games due to injury but was highly effective with a 7-2 record and a 2.88 ERA. His ERA would remain under 3.00 the next season at 2.82 and in 1998 he won 20 games for the second time in his career. Cone also pitched a perfect game against the Expos during the 1999 season. In six seasons with the Yankees Cone went 81-51 with a 3.13 ERA, was a two-time All-Star and won four World Series.

With numbers and accolades like that the Jays must have got a good haul in return for Cone right? No, doesn’t do justice to that question so let’s just put it this way. In six years with New York Cone won 81 games. The three pitchers the Jays got from the Yankees for Cone won a combined six games in the Majors in their careers. Two of those players, Mike Gordon and Jason Jarvis never threw a single pitch in a Major League game. The other was Marty Janzen.

Janzen was supposed to be the jewel of the Cone trade for Toronto. During the 1995 season in the minors split between the New York and Toronto systems Janzen appeared in 28 games and posted a 16-6 record and a tidy 2.87 ERA. He also struck out 8.1 batter per nine innings and had a respectable 1.12 WHIP. The following season in AAA Syracuse the wheels started to fall off. In 10 starts at AAA Janezen was roughed up a lot and posted a 3-4 record and a 7.33 ERA.

Despite those struggles he still made his Major league debut that season. In his debut on May 12 out of the bullpen Janzen actually picked up the win after pitching three shutout innings. He also turned in a solid outing in his first career start a few weeks later, holding the White Sox to three runs over seven innings. In his next two starts though he was pounded for 15 runs in 11 innings. After starting the season 3-0, Janzen would win only one more game the entire season and his ERA quickly ballooned from 1.84 to 7.33 by the end of the season. In his final outing of the season the Tigers feasted on him for seven runs in 4 2-3 innings.

In 15 total appearances in 1996 Janzen went 4-6 with a 7.33 ERA. In 1997 he continued to struggle at AAA with a 0-5 record and a lofty 7.20 ERA. He did make 12 appearances with the big club that season, but they were all out of the bullpen, as he went 2-1 with a 3.60 ERA. Following the ’97 season Janzen was left unprotected in the expansion draft and was snatched up by the Arizona Diamondbacks. The D-Backs sent Janzen back to the Yankees in a trade a few months later, but he never appeared in a Major League game again.


1. 2001 Blue Jays traded David Wells and Mat DeWitt to the Chicago White Sox for Mike Sirotka, Mike Williams, Kevin Beirne and Brian Simmons

Good ‘ole “Shouldergate.” Just thinking about this trade and how the Jays got duped makes me feel sick. David Wells returned to Toronto prior to the 1999 season as the major piece of the Roger Clemens trade. In two season he won 37 games, including 20 in 2000 when he finished third in Cy Young voting. It was no secret that Wells hated playing in Toronto and the trade to the White Sox before the 2001 season was no surprise. Wells spent only one season with the White Sox, posting some of the worst starting numbers of his career with a 5-7 record and a 4.46 ERA. At least he actually pitched though! Wells returned to the Yankees the following season and would win 15-plus games three more times in his career.

Matt DeWitt never played a game for the White Sox and was quickly dealt back to Toronto for Mike Williams three months after the Wells deal. He signed with San Diego as a free agent following the 2001 season. He played in only five games for San Diego and never appeared in the Majors again after 2002 while playing in the Minors with Cleveland, Baltimore and Milwaukee.

The big piece heading to Toronto in the Wells deal was supposed to be Mike Sirotka. In 2000 Sirotka won 15 games and posted a 3.79 ERA for the White Sox. The southpaw looked like he was coming into his own at only 29 years of age. Blue Jay fans would never get to see Sirotka pitch in Toronto.

After the trade it was discovered that Sirotka had a damaged shoulder and needed surgery. The surgery proved to be career ending as Sirotka never pitched a single inning in the Majors again. Toronto GM appealed to the Commissioners office to have the trade overturned due to information of Sirotka’s shoulder being withheld by the White Sox. However, the blame realy fell on the Blue Jays medical staff who examined Sirotka’s shoulder and found no issue. Bud Selig ruled in favor of Chicago and Toronto ended up with Sirotka’s dead shoulder.

The other pieces of the deal also proved to be useless to the Jays. Mike Williams was shipped back to Chicago for Matt DeWitt, while Kevin Beirne saw limited action out of the Toronto bullpen in 2001. It was likely limited due to the fact he surrendered 10 runs in only seven innings. Brian Simmons saw the most time on the field for Toronto, appearing in 60 games in 2001. Those 60 games didn’t mean much though as he hit a paltry .178.

Now that you’ve seen the list time for a GM count. From the 10 trades that made the list eight of them were made by Gord Ash. Eight! That means one goes to J.P. Ricciardi and one goes to Alex Anthopoulos. If you wanna know why the mid to late nineties and early 2000s were so bad in Toronto there’s part of your answer.

Agree with the list? Or, maybe disagree with it? That’s cool too. Let me know in the comments section below.

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3 thoughts on “Jays Listed: Top 10 Worst Trades

  1. Peter DeMarco Reply

    The Mike Stanley deal does not deserve to be on this list as this was actually a good deal for the Jays as it was an addition by subtraction type of a deal. Stanley’s presence on the Jays actually hurt the team and getting rid of him for nothing was a good move. The Jays went on to have a 35-19 record after trading him to the Red Sox.

    Also, the Jays later traded Peter Munro for fan favorite Dave Martinez.

    Maybe replace this deal with trading future Cy Young award winner Pete Vuckovich for Victor Cruz and Tom Underwood.

    • David Harrison Reply

      See your point on the Stanley deal Peter. That was one of the last one’s to make the cut and is more of a point of view on the trade than a rip off like some of the others.

      Good call on the Vuckovich trade too. I shouldn’t have missed that one! thanks.

  2. Dan Winegar Reply

    Mike Napoli ouch! That could go on the list for the Angels too!

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