The Twins Worst Trades: Johan Santana

There is no doubt Santana was 1 of the best Twin that didn't make it to the HOF. IMO he was the best pitcher the Twins ever had in the short time he was a starter for them. The trade was regrettable but Twins were desperate. As things worked out it'd have been better if the Twins would have held onto Santana & wait for a better trade & if that wasn't possible keep him & let him become a free agent. 

The J.J. Hardy for Gomez trade was not such a bad trade.  In the seven years following the trade, Hardy put up 17.3 WAR and Gomez put up 19.8 WAR of which 12.8 was in the 2 years of 2013 and 2014.  Over his career Hardy had slightly better WAR 27 to Gomez's 24.  All data is from fangraphs.

The problem was trading after one year Hardy and Brendon Harris to Baltimore for and Jim Hoey and Brett Jacobson.

If I remember correctly the reason why the Twins could not work out a contract extension with Santana was because they traded away Luis Castillo, a good teammate and buddy of Johan's. He was upset that the Twins were not adding pieces to get better and losing Castillo indicated to Johan that the Twins weren't committed to winning. Revenue might have been the deciding factor but Johan also wanted to play for a team willing and able to acquire the necessary pieces to win.

I was hoping for a trade with the RedSox. I wanted Ellsbury.

Thanks for bringing up this salty open sore in Twins history CODY!!!

I felt at the time that if the package wasn't right, the Twins should have held onto him and then taken the extra draft pick when he walked at the end of the year. It would have been one thing if the Twins were rebuilding at that time, but they weren't. They ended up losing the division by one game in 2008 and missed the playoffs. Santana would have made all the difference.

Smith was dealt a bad hand, but I can't think of one trade that didn't blow up in his face. 

I liked the rumored packages from the Yankees and the Red Sox better than the Mets by a lot, so I will always wonder what was really out there. It felt like at the time the Twins were afraid to trade with the Yankees for some public relations reasons and that the rumors about the Red Sox interest weren't that solid (i.e., they weren't really "in" just trying to raise the price for the Yankees).

Go-Go was incredibly fun to watch in the outfield, but he was just helpless at the plate as a Twin. Would things have gone better if he'd had better/more development time? It seems likely, since he never set the world on fire as a hitter in the minors and had been an awful hitter in the majors for the Mets. Defensively, he was ready but offensively he needed more work. But buy, his D was great until he started losing that incredible speed.

I recall Guerra being talked about as the guy with big upside, and it's a reminder that a-ball guys in trades are often just lottery tickets and will bust out much more often that blow up.

Humber & Mulvey were over-valued by the Twins because they were "close" to being MLB ready, I think. No way does the current office make that mistake today.

If they did nothing and just let him walk in free agency, they'd likely have won the AL Central in 2008 by 3 or 4 games instead of losing that game 163 in Chicago. 

It was odd how letting him walk was never an option on the table at the time discussed publicly (and isn't even discussed in this article). But sometimes doing nothing is the best move. 

I look at the package we got and find it depressing.  Your essay needs to be wrapped in a black ribbon.

If they did nothing and just let him walk in free agency, they'd likely have won the AL Central in 2008 by 3 or 4 games instead of losing that game 163 in Chicago. 

It was odd how letting him walk was never an option on the table at the time discussed publicly (and isn't even discussed in this article). But sometimes doing nothing is the best move. 

This is a good point. Keeping a final-year star rather than trading for prospects is just like trading prospects for such a person without the likelihood of a re-signing. You end up with one year of the star but fewer prospects.

The prospects we got didn't turn out very well. And sometimes the prospects we don't give up in a trade for a Lindor, say, don't work out either. But at least we have much better information about our own prospects than about those we get in trades.

I think it is important to remember that Johan had no trade or limited trade clause that really tied the Twins hands.

You had to look at the trade in one other way. The Twins saved $120+ million. Then the question comes, what did they do with that money instead of keeping one of the best players ever that pitched in Minnesota as part of the team for years and years.

I also seemed to remember that Mike Pelfrey's name was bandied around in the Mets package.

Yeah, what was the main Yankee package: Hughes, Cabrera, Kennedy, Chamberlain. I'm not sure what was the tell on that trade. The Twins didn't want Caberra?

I liked the throw-ins of Lowrie and Bowden at the time. It was just what starting arm (Bucholz or Lester, Ellsbury or Crisp). Remember Ellsbury was still an unproven at that point.

I always kind of felt like Denard Span was partly to "blame" (please note the quotes, blame isn't exactly the right word). He was the heir apparent to Torii in center but he had seemingly stalled out a bit in the minors, so the Twins felt like whatever they got for Santana had to include a CF. 

 

On the flip side, the trade seemed to light a fire under Span's butt and he was a much better player after the Twins got Gomez. 

 

Also, don't forget the impact of Terry Ryan leaving Bill Smith to hold the bag that offseason. 

^^ That!!!   Specifically Ryan leaving and giving Bill Smith the job of dealing with Johan.  That was a straight garbage move.   

At the time I thought the Santana deal was ridiculously bad for the Twins and time has proven that to be true. Bill Smith just wasn't up to the task and was taken advantage of by the Mets. If he had a bit more backbone he would have just kept Santana and gone all in for a playoff run. Getting 200 innings from Santana plus at least a couple playoff starts would have been significantly more valuable than the crap package they got back.

At the time I thought the Santana deal was ridiculously bad for the Twins and time has proven that to be true. Bill Smith just wasn't up to the task and was taken advantage of by the Mets. If he had a bit more backbone he would have just kept Santana and gone all in for a playoff run. Getting 200 innings from Santana plus at least a couple playoff starts would have been significantly more valuable than the crap package they got back.

Feels like Billy Smith tried to play the Yankees and Red Sox against each other and get them in a bidding war and then both of them bailed out completely and he went to the 3rd place team out of desperation and convinced himself their prospects were worth it.

Clearly a trade with Boston would have worked out better, based on the three names mentioned and how they did, assuming they would have done similar things in MN, no evidence they would have.  The NY guys were all ehhh with big spikes in their careers but nothing super.  

I would not say the trade of Gomez for Hardy was bad, as Hardy was a good SS for years, just not with the Twins because we gave him to Baltimore for basically nothing.  Had we stuck with Hardy and he was similar to what he did in Baltimore that would have been a fine trade.  

Really, the whole thing showed how bad Smith was.  He did make some good international signings, but his trades were mostly very bad.  He also made some bad international signings as well.  He should go down as worst GM in Twins history.

 

Also also, I will never forgive Gardy and the Twins for mishandling Hardy. He hurt his wrist, still had an average season offensively for a shortstop while playing good defense, the Twins decided Hardy was a disappointment and shipped him off for Hoey/Jacobsen and sign Nishioka, and then Hardy's wrist received better treatment while with the Orioles and he returned to being a top shortstop. It's no wonder that "total system failure" resulted. 

I think it's way worse. I believe Gardy's treatment of Hardy, the trade, and putting Nishioka on the field lost him the clubhouse. And a championship caliber team turned into doormats for almost a decade.

I think it is important to remember that Johan had no trade or limited trade clause that really tied the Twins hands.

That is important and though Santana made it clear he would not consent to a trade mid season I would have called his bluff.     If the Twins were out of it and he could have been traded to a contender I am guessing he would have jumped at it.    I would have gone for the Lester trade even up but what I remember was arguing for keeping him for the year if they didn't get an amazing deal.   So often fans balk at the idea of paying gigantic amounts for multiple years to free agent pitchers because of the risk and I am one of them so the idea that we had to get rid of him because we couldn't keep him long term was just silly to me.   If Santana was on the free market for 11mil for one year anyone would jump at it but because we already had him the idea of keeping for that year at that price wasn't appealing?   Just seemed silly to me.   Very likely cost us a playoff spot.   Conceivably cost us a shot at a WS.

 

Yeah, what was the main Yankee package: Hughes, Cabrera, Kennedy, Chamberlain. I'm not sure what was the tell on that trade. The Twins didn't want Caberra?

 

I liked the throw-ins of Lowrie and Bowden at the time. It was just what starting arm (Bucholz or Lester, Ellsbury or Crisp). Remember Ellsbury was still an unproven at that point.

I recall that although the Yankee offer was originally reported as Hughes AND Kennedy, it became Hughes OR Kennedy.  Not sure in the Yankees changed their minds or that the original details were incorrectly reported.

Jon Lester had, in the latter part of 2006, been diagnosed with a rare form of non-Hodgkin's lymphoma.  At the time of trade it was not clear that he would remain in remission ( in young men non-Hodgkin's lymphoma has a 5 year survival of about 84%) . Therefore the Twins had wanted more than Jon Lester. (In 2007 Lester appeared in 11 games with an ERA of 4.57 and an FIP of 5.24

I am a little confused about the link below as they are reporting Lester's cancer to be both a lymphoma and a blood cancer.  I don't really understand that.

http://archive.boston.com/sports/baseball/redsox/articles/2006/09/02/lester_diagnosed_with_cancer/

... though Santana made it clear he would not consent to a trade mid season I would have called his bluff. If the Twins were out of it and he could have been traded to a contender I am guessing he would have jumped at it.  ... 

I completely agree. Teams are desperate for pitching mid-season. Teams are desperate for pitching while they are trying to keep their arms healthy and their bullpen from getting worn out.

Teams are desperate to deal when they want to put the best arm they can out on the mound to start games.

I don't know that the Twins got the best package possible for Santana during the off-season.