Hard to top the '88 one. I mean, what kind of person thought Campusano was a better prospect than Ducey, Fielder, and any number of others who were blocked at the time? Sheesh. The Jays were addicted to athletes and Campy was the peak of that addiction.

For other moves that seemed dumb at the time... Ash thinking that salaries would go down after the strike in '94 thus waiting until after the '95 season to sign Alomar certainly ranks up there. For players Tony Fernandez listening to a dumb agent who told him the $1.5 million offer from the Jays post-93 was an insult then Tony had to take under $800k from the Reds to play third when no other offers came about.

I absolutely hated the Roger Clemens trade when it was made.  I had been somewhat supportive of Gord Ash up to that point, but my opinion of him changed significantly when he completed that one.

I understand why Clemens probably needed to be traded, but I hated the short-sightedness of the deal at the time.  Wells and Lloyd were both on the wrong side of 30 and both were in the final year of their contracts.  Lloyd, a lefty specialist who had pitched less than 40 innings in the previous season, was not someone I would've wanted in exchange for the team's most valuable commodity.

I also wasn't crazy about Homer Bush at the time and the belief that he was going to put an end to the team's revolving door at second base.  Often cited as justification for his inclusion in the trade was the fact that he'd hit .380 in 1998, but that was in just 72 at-bats and had fluke written all over it, especially since his minor league record was rather unremarkable.  I believed he was going to be significantly below average as a regular player.

The trade worked out reasonably well for the Jays, at least in 1999.  Wells was a passable starter that year, Lloyd was usually reliable out of the bullpen in his 72 innings, and Homer Bush turned out to be a big surprise.  Things changed after that year, with Lloyd leaving for Montreal at the end of the season, Bush battling injuries and poor performance during his remaining years, and Wells being shipped off to Chicago after the 2000 season for essentially two spare parts in Kevin Beirne and Brian Simmons.

My preference would've been to use Clemens to acquire some younger major league-ready players who could have not only helped the team in 1999, but in the future as well.  Even under a best-case scenario for this trade, the Jays probably would've only had Homer Bush to show it within two or three years.  I understand the constraints Ash was under at the time, but I still don't feel he got particularly good value for Clemens, all things considered.

The whole Clemens-Wells thing stands out as one bad decision in my mind.  In return for the greatest pitcher of all time, coming off two of the best seasons of all time (think about that for a minute), they got a reliever, journeymen second basemen, and above average pitcher, who they then traded for an injured pitcher?  The Ash Jays were like a well run version of the Pittsburgh Pirates - they'd sign enough veterans to never lose badly, but never make the moves to win big.  Both the Clemens and Wells deals were trades that the Jays could have won big, but instead they took the... I don't even know if it was the easy way, but it was the wrong way.

Do your best to consider moves that actually worked out okay for the Jays

Like tossing Dustin McGowan into the rotation this May. Dumb, I stil say - but it worked out great.

Wells for Sirotka worked out poorly, but it wasn't a completely dumb idea.

The trade that brought Carlos Garcia and Orlando Merced (along with Dan Plesac) made me crazy. They didn't give up much of anything (well - Craig Wilson and Abraham Nunez), I just didn't want those two guys on the team.

Signing Otis Nixon - Shannon Stewart was ready!

Cito Gaston playing Pat Borders instead of Greg Myers against Minnesota in the 1991 playoff. Myers absolutely wore out the Twins that year (9-16 - .563!!). More important, he could actually catch Candiotti's knuckleball. Which Borders couldn't do, and Candiotti became reluctant to throw his only quality pitch. That worked out great.

Obviously, the Sil Campusano Project gets my vote - it looked dumb at the time, and it could hardly have worked out worse: they basically lost two fine young prospects (Cecil Fielder and Campusano himself), the physical deterioration of the brilliant outfield continued without respite, and Rob Ducey never did get the opporunity he needed and deserved.

I think the Shawn Green for Raul Mondesi trade was the worst. Ash traded an elite hitter just reaching his prime for someone whose best days were behind him. Mondesi played the same position, but was worse in every single way and was ridiculously overpaid. On top of that, they guaranteed his next two option years. Sadly, it was a typical trade for Gord Ash.

I think the Shawn Green for Raul Mondesi trade was the worst.

Well, not one of Gord Ash's greatest moments. But not as bad as dealing Michael Young for Esteban Loiaza, surely?

But it's often forgotten that Shawn Green forced the  trade. He wanted out of Toronto. It wasn't like Ash woke up and wanted to trade Green for Mondesi. But he did want to get something for him in return. He probably would have done better with the Dodgers other corner outfielder, who didn't make quite as much money (a fellow named Sheffield).

A couple of other things - while Green looked like he was becoming an elite hitter (he was coming off a tremendous season, and he was just 27 years old), as it turned out he didn't actually become one. He's had three great seasons (1999 in Toronto, 2001 and 2002 in Los Angeles) - but over the rest of his career he's been a pretty good player, but no more. Hardly a star.

Mondesi was just two years older than Green, a better outfielder, a better baserunner, and a right-handed power bat (three 30+ homer seasons in Dodger Stadium) to go with Delgado. He was a hustling player, a guy who played the game hard. Unfortunately, he lived just as hard off the field and was completely unfamiliar with the concept of "taking care of your body." Which is the main reason Green is still around, and Mondesi isn't.

But it's often forgotten that Shawn Green forced the  trade. He wanted out of Toronto. It wasn't like Ash woke up and wanted to trade Green for Mondesi. But he did want to get something for him in return.

As I recall, Green indicated he was likely to leave as a free agent the following year, but he was willing to wait until that time.  I think "forced" is too strong a word here.  Green's decision may have led Ash to believe a trade would be prudent, but Ash certainly didn't have to trade him.  Ash had the choice.

To be honest, it would have been better for the Jays to simply let Green leave as a free agent and receive the draft picks from the team that signed him.  I actually argued this at the time.  Mondesi was a terrible use of the team's financial resources.  The team could have used the money saved and acquired a cheaper player with little or no drop in production and have money left over to improve the team in other areas.  I forget what outfield alternatives were available at the time (I think Bobby Higginson was one), but I do know there were several possibilities out there.

Well, for Lloyd we did get 2 draft picks and they were used for Dustin McGowan (sandwich pick) and Pete Bauer (2nd round, never made it out of the minors from the looks of it).  Not bad for a loogy eh? 

Just a reminder of how valuable draft picks can be.  Clemens might be retired now, Lloyd is long retired, Wells might be too yet McGowan should give the Jays a few more solid years before free agency (heck, before arbitration!).

An FYI on compensation picks...
2004: For Kelvin Escobar: Lind and Zack Jackson
1996: For Robbie Alomar: Joe Lawrence & Pete Tucci (ick)
          For Al Leiter: Brent Abernathy (later traded for Mark Guthrie & Steve Trachsel) & Clayton Andrews
1993: For Tom Henke: Chris Carpenter & crap
          For Jimmy Key: crap
          For David Cone: crap
          Lost for signing Paul Molitor: crap (Kelly Wunch)
          Lost for signing Dave Stewart: minor league crap

Not a lot of picks gained or lost over the years from what I can tell.  Weird.  The 1993 setup worked nice, getting a few years of Carpenter, Molitor, and Stewart for Tom Henke, Jimmy Key, and David Cone.  '96 sucked though and '04 is on the edge of sucking.

coming off two of the best seasons of all time (think about that for a minute)

For a minute, hah!  I've been thinking about it every time I watch the Jays. It haunts me. Those seasons were indescribable.

But a few weeks ago I found a tidbit of information to satisfy my schadenfreude: the active leader in CG and SHO has only 4 complete games and 2 shutouts in the nine seasons since he left Toronto.

One shutout was against Frank the Cat and his hapless Detroit Tigers (featuring Frank as the first baseman, need I say more) box.

The other shutout was in 2003 against David Eckstein the DH and the Vladless Angels. box

Why do I take joy in this? Because how much I enjoyed watching every Clemens start watching to see if he would go the distance and go for a shutout, which he seemed eminently capable of every time he took the ball.

He's had some good times (two more Cys) and bad since he left, but he's not going to end up nearly as high on the career shutouts list as he seemed he might before he so sweetly requested to go to a real baseball team.

It hurt to see him go, but like getting dumped by someone you adore. He'd never be so great again, but at least we have the memories of 1997.

Back on topic, I wish baseball allowed the trading of future draft picks. Because Ash should have landed a handful of first rounders.

I was going to say the Randy Myers signing in 1998, but after looking at it in more detail, it ends up being worse in retrospect than it was at the time.

Cons:

• The Jays probably did not need to make him the highest paid reliever not named Wetteland
• His WHIP was always a bit on the high range
• He was at an age where pitchers are generally on the decline

Pros:

• He had a great year in 1997. 
• Lets Escobar move into the rotation, where help was terribly needed.

So even though I didn't like it, it was sort of understandable.  Plus, claiming Myers off of waivers should probably be considered San Diego's worse move ever, so it wouldn't be fair if the same contract is considered in Toronto's worse move ever as well.

Wells for Sirotka may not have been dumb, but missing the torn labrum in the first examination was pretty bad.  The Young/Loaiza trade is up there too.

Since it hasn't been mentioned yet, I'll throw my vote to the Cone trade in 1995.  He went to the Yankees for essentially nothing.  I would considered it a reasonably good idea if it is looked at as a pure salary dump.  But since it was positioned as a trade to get better by Ash, I can't help but think that better prospects(Rivera) could have come the other way. 

2 classic trades of Ash's:

• John Olerud AND $5 million for Robert Person
• David Cone for Marty Janzen & a couple of no-names

And there's one of the Jays' first trades-not-made:  Just prior to their opening season, Gillick had swung a deal to trade Bill Singer to the Yankees for Ron Guidry, but it was nixed by his boss, Bavasi. According to Gillick, one of the reasons his deal  was turned down was that the media guide had already gone to print with Singer's photo on the cover, and it wouldhn't have looked good to trade away their "poster boy"... 

The David Cone for Janzen deal is worse than it seems as it became the reason Ash was scared to death of trading for youngsters and probably encouraged him to trade them away. I remember an interview he gave once where he said something about how the Janzen trade taught him not to trade for prospects as you don't know what you are getting.

The Singer for Guidry trade that never happened was also a turning point as it taught Bavasi, and the Jays in general, to trust Gillick and let him do his thing from that point forward.

Thus two trades, one made, one not, helped shape the team for two different GM's tenure. One made the GM so scared of prospects he wouldn't even consider them as the keys to a trade and would dump them in a second for a 'proven vetern'. The other made the ownership recognize the value in trusting the guys they hired to run the team and to get out of the way, thus allowing many trades to occur that may have been blocked by management at one time (the Barfield and Upshaw trades come to mind as both were popular and an interfering owner might have blocked them).

No mention of the Prokopec deal yet? :)

It was a bad trade, not only for trading 2 assets, which could have helped the Jays at least in the short term, but it also made JP very gun shy for a couple of years.  It really hindered his GM style and for a while was only making little itty bitty dink and dunk type of moves.  Heck, it probably STILL has impacted his ability and confidence in trading for any young players.

Michael Young for Esteban Loaiza seemed a reasonable trade at the time, and a year or so later it looked like Loaiza was much more valuable than Young as he was one of the AL's top starters. Unfortunately, the Jays had let him go to the WhiteSox by then. I think it could be argued that THAT was the poor deal - letting Loaiza go just before he had his near-Cy season.

I agree about Michael Young. There was nothing in his minor league record that screamed out "big things ahead". He hit well enough in the minors, but was old for his levels.

Miguel Tejada is a subject of discussion in another thread, and I find it interesting how perceptions compare with reality when it comes to these two. They are virtually the same age and had virtually the same OPS+ in 2007 (109 for Tejada, 107 for Young). One is seen as a player in freefall while the other is seen as an all-star.

I've always been intrigued by, "The Sil Campusano Project."

Sil was a "can't miss" prospect. BUT, not only were we wrong but so was Basball America and most other commentators. Everybody thought this guy was "can't miss." When you think of us mucking about with a Moseby, Barfield and Bell outfield to put this kid in it makes your brain hurt.

Definitely a bad trade, but IIRC, the Prokopec trade was basically a salary dump as were most of JP's first year deals.

It should also be pointed out that Prokopec was a pretty good pitching prospect.  He just had the misfortune of suffering a career-derailing injury.  I really liked the trade at the time.

Ryan, I thought the trade was bad, but not terrible at the time.  I was a big Quantrill fan, and I liked Izturis.

I just think the biggest impact that it had was it really affected the way business was done with the Jays.  JP was completely afraid of making any real big deals for a while after that.  Let alone for a young player.  Have we brought in a single young player as a centerpiece to a trade since Prokopec?  Santos at best can be argued as a throw in (maybe that is a little harsh, but his value was in the tank).

Here's a dumb move for you: releasing David Wells after the '92 season. They just let him walk away, because they didn't like him. Well, I can understand not liking him, but... guy's had quite a few good seasons since then, and it might have helped if he had had a few more of them here.

I won't elaborate on the one's already discussed but a ranking would go like this for me:

1. Clemens deal - verbal agreement or no, keep him
2. Green deal - for already explained reasons
3. Cone deal - like Clemens, further compounded because you never EVER help the Yanks
4. Guidry non-deal
5. The Felipe Lopez deal. Maybe I just can't let it go but Arnold and JFG was such a useless return for a kid who had been touted as worthy of making the big 3 into the big 4....I still hate that deal even though the wheels are coming off Lopez

Yes, Caramon, Ricciardi has traded for a young player since Prokopec. He traded Hillenbrand for Accardo.

Does anyone know who we ended up picking in the draft when Escobar signed with the Angels? I liked that JP let him walk, but his contract has been a bargain for the Angels so far. Does anyone remember the years and dollars he signed for?

Brent - looking back a few posts you will see
2004: For Kelvin Escobar: Lind and Zack Jackson

So good picks but nothing great.  One might become another Matt Stairs while the other was a key piece in the trade for Overbay. 

I'm pretty sure the Angels signed Escobar to a 3/18 deal - I expect he's since signed another deal, but don't recall

For contracts I always check http://mlbcontracts.blogspot.com - Cot's Baseball Contracts.

Escobar is listed there as signing at first for 3/$18.75 then an extension for 3/$28.5 in early '06 which covers the 07-08-09 years.  The Jays never paid more than $3.9 million for him.

There have been some pretty terrible moves made by the Jays over the years (many of which were detailed above), but I really can't see how any trade could be worse than the Olerud for Person trade.  Olerud was coming off his age 27 season, during which he had posted an OPS+ of 116.  This was viewed as the continuation of a disappointing trend, since he had followed up his historic age 24 season in 1993 (363/473/599 for an OPS+ of 183!!!) with seasons of 124, 111 and 116.  Still, this was an above average defensive first baseman, in the prime of his career, with a history of being an above average bat and the proven ability to be (at times) a superstar caliber hitter.  Person was a pitcher coming off his age 26 season (his rookie year) in which he posted an ERA+ of 89.  Granted, this was a salary dump to a certain extent (although the Jays GAVE cash in the deal), but Olerud was a player that should have had tremendous trade value, and all the Jays ended up receiving for him was a spare part.  All of this point to the trade being, at the time it was made, an obvious mistake (something that CANNOT be said about the Young/Loaiza deal, as bad as it ended up being).

The results of the trade just confirmed the belief at the time that this was a terrible trade.  Olerud went on to post OPS+'s of 135, 163 and 128 over the next 3 years with the Mets, while continuing to be an excellent player with the Mariners for the next 4 years after that.  Person, in his two seasons with the Jays, posted ERA+'s of 81 and 65 before being moved to the Phillies for Canadian lefty and current Toronto Maple Leaf Paul Spoljaric.

As I said at the start - the Jays have made some bad moves over the years, but none were as bad as this one.  This was a crushing blow, especially when you consider that the Jays choice of whom to get rid of essentially came down to Olerud or Joe Carter, who would have probably returned more in a trade if he was dealt at the time (rumours at the time had him going to the Braves for Jermaine Dye) and went on to post an OPS+ of 77 the following season, his last with the Jays.  The choice should have been obvious at the time, but Ash was blinded by Carter's reputation as a world-class "RBI Guy" and his local popularity.

Anyway, thats my case.  Sorry for the rant, but this move still makes my blood boil after all these years.

forgot all about that, the Olerud deal would have to slip in at #3 or 4 on my list.

Also, I thought letting Esco walk was a big screw up. Possibly worthy of my top 10.