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Let’s (not) make a deal


With the Pirates still in contention in the National League Central Division in late June, talk is turning to their trading for a power presence to add some pop to the middle of the batting order.

Obviously, Jose Bautista — aka Joey Bats – could have filled that role had he gone from Baseball Vagabond to the Game’s Best Slugger with the Bucs instead of the Toronto Blue Jays.

Bautista is following a 54-home run, 124-RBI breakthrough 2010 with another season of unprecedented power numbers, at least for him. By going 1-for-3 with three RBI, including a fourth-inning home run off Kevin Correia, Bautista is tied for the major-league lead with 24 homers to go with 52 RBI this season. He never hit more than 16 homers or 63 RBI in his three seasons with the Pirates, from 2006-08, before being dealt for Robinzon Diaz.

Which brings me to the worst trades in Pirates history.

At least, in my lifetime.

My colleague, Bob Cohn, tells me that you evaluate a trade the same way you do talent: You know it when you see it. In that case, Bautista-for-Diaz will go down as one of the most lopsided deals in club history.

While Bautista showed some flashes of power with the Pirates, they never could have predicted this. (Nor could they have afforded him the next four seasons at $14 million per, although his five-year deal with Toronto is looking like a bargain).  Here’s a look at Bautista’s numbers with the Bucs:

Year    Games HR      RBI     BA      OBP    SLG    OPS

2006    117      16        51        .235     .335     .420     .755

2007    142      15        63        .254     .339     .414     .753

2008    107      12        44        .238     .313     .405     .718

Perhaps the Pirates gave up on Bautista too soon, but the Blue Jays deserve credit for tweaking his plate approach and cultivating his power in 2009, when he batted .235/.349/.408/.757 with 13 homers and 40 RBI in 113 games. That’s why I’ll leave Bautista off my top five worst trades:

5. Chris Young and Jon Searles to Montreal for Matt Herges (2002): What makes this trade so bad is not that the Pirates had invested a million-dollar signing bonus on the 6-foot-10 right-hander, a 2000 third-round pick out of Princeton, or that he has a 49-34 record and 3.74 ERA over eight seasons but rather that they cut Herges in spring training.

4. Willie Randolph, Dock Ellis and Ken Brett to New York Yankees for Doc Medich (1976): A one-sided deal that ranks among the worst in baseball history, according to Traded author Doug Decatur, who ranks such things. I’m more forgiving, even though Randolph was a six-time All-Star, because Medich was involved in a nine-player trade with the Oakland A’s that brought second baseman Phil Garner to the Pirates, who won the 1979 World Series. Garner was twice an All-Star with the Bucs, in 1980 and ’81.

 (An aside: Garner also had one of the best nicknames on a team full of them, as those Pirates had Willie “Pops” Stargell at first, Scrap Iron at second, Bill “Mad Dog” Matlock at third and Dave “Cobra” Parker in right).

3. Jason Schmidt and John Vander Wal to San Francisco for Armando Rios and Ryan Vogelsong (2001): In an ominous sign for Dave Littlefield, this was his first trade, the Pirates dealt their 28-year-old ace before he hit free agency. Schmidt only went 78-37 with a 3.36 ERA with the Giants and twice was a top-five finalist for the Cy Young Award. Neither Rios nor Vogelsong made much of an impact here.

2. Aramis Ramirez and Kenny Lofton to the Chicago Cubs for Jose Hernandez, Bobby Hill and Matt Bruback (2003): This was a straight salary dump for the cash-strapped club, which was in violation of MLB’s debt-ratio rule. But to give away not only Lofton, one of the best leadoff hitters in baseball, but also the franchise player Ramirez, who had five consecutive seasons of 25 homers or more, was a crime that became even more cruel once we got a look at Hernandez and Hill. The Pirates have been searching for a long-term replacement at third ever since.

1. Willie Greene, Scott Ruskin and a player to be named later to Montreal for Zane Smith (1990): This is where you can feel free to disagree — and I expect many of you will — because Smith delivered. He was 6-2 with a 1.30 ERA in 10 starts, including three complete games and two shutouts, to help the Pirates win a tight NL East division race. That earned Smith a four-year contract with the Pirates, and he went 47-41 with a 3.35 ERA in that span, including 30-20 between ’90 and ’92, when the Pirates won three consecutive division titles.

But what transpired between Aug. 8 and Aug. 16 of 1990 is what sours me on this deal. That the Pirates included the top prospect in their farm system only conspired to set them on an 18-year streak of losing seasons. That’s because the “player to be named later” was outfielder Moises Alou, a former first-round pick (No. 2 overall in 1986).

Giving up Greene, another a former first-rounder (18th in 1989), was worth it even though the third baseman/right fielder played nine seasons in the majors. He had a career .234 batting average, hit 86 home runs with 307 RBI. And Ruskin, who was 2-2 with a 3.02 ERA with two saves with the Pirates in ’90, was 11-9 with a 3.95 ERA in four major-league seasons.

But Alou became a six-time All-Star in 16 seasons, hit 332 homers and had career numbers of .303/.369/.516/.885. He could have been the star player the Pirates so desperately needed to replace Bobby Bonilla in right field and in the cleanup spot, the All-Star to fill the void when Barry Bonds left.

Instead, we watched a slow, steady decline.

What makes the Smith-for-Alou deal so bad in my eyes is that the Pirates mortgaged their future for a chance to win a World Series. While Smith helped them win three consecutive division titles, the Pirates never won the pennant, let alone played for the world championship in those years. The Pirates could have included any other player in their system and the deal would have been a smashing success — Bleacher Report still ranks it as one of the top 10 waiver-wire deals — but adding Alou was a major mistake.

That should serve as a warning to Pirates GM Neal Huntington when looking to make a deal so this club can contend for a championship. It’s one thing to add a valuable piece to your club, but be careful that you don’t give up a more valuable one in the process.



  1. PokeyReese says:

    It doesn’t surprise me that I am the only one to comment on this irrelevant article. The Pirates are in the hunt and the fans actually have some hope this season so this moron decides to write this garbage. This article is overdone and outdated. The only reason I even saw this was because I was making my way to DK’s blog. You are a joke and unoriginal. This stinks of the trash that the Trib is known for outside of DK.

  2. chris says:

    You’re SUPPOSED to mortgage your future when you have a chance to win the World Series. That’s the time to be aggressive and forget the future and try to win now, even if it means trading away elite prospects. The Zane Smith deal was a brilliant trade that nearly helped the Bucs get that championship. You may have disliked including Alou in the deal, but calling it the worst trade in history, when it nearly helped the team win a title, is disingenuous, and was clearly done merely to make people angry and stir the pot. You can’t possibly believe in all honesty that was the worst deal this team has ever made.

  3. Kevin Gorman says:

    @Chris: Nothing disigenuous about it, and it wasn’t done to “make people angry or stir the pot.” I didn’t call it the worst in history, just my lifetime. The Pirates mortgaged their future for a slightly above-average player, not a superstar, and didn’t win the pennant, let alone the World Series.

  4. Better Days Coming says:


    One critical piece to the Smith trade was not just that he was a quality lefty, but he was a Met killer. He had an exceptional record against New York, the team to beat in the NL East and the Bucs went out and got him.

    I’m not questioning your motives but I think that’s a critical piece to the equation.

  5. Hford89 says:

    Can’t cite nicknames from the ’79 Buccos and leave out “The Antelope” — Omar Moreno!

  6. Rich says:

    The Zane Smith trade is one of the best trades in Pirate history. They took a shot and Smith got them over the hump that was the NY Mets to win the division. He dominated the Mets. Without Zane, the Bucs don’t win the division 3 straight years. Clearly NOT a bad trade and certainly not worse than the other on your list as well as many more.

    And you are only able to say this is a bad deal after 18 years of hindsight and Alou becoming a very good player. That’s too much time. When the deal was made it was a no brainer great deal. Every other trade on your list was a loser from the moment it was announced (though I don’t recall the feeling on the Doc Medich deal). Even several years after the Smith trade was made, nobody thought it was a bad deal. Having Alou on the team probably wouldn’t have prevented 18 years of losing anyway. He would have been gone quickly in some other deal.

  7. IA Pirate says:

    Trading Johnny Ray to the California Angels for Miguel Garcia and Bill Merrifield was a disaster too. I would have loved to have seen Ray hit with guys like Bonds, Bonilla, and Van Slyke in the lineup.

  8. Kevin Gorman says:

    @BDC: Good point about Smith being a “Met killer,” but my point is that the Pirates gave up too much just to win the division title (albeit three consecutive years). They gave up a rookie pitcher and two first-round picks who spent a combined 26 years in the majors — including one who would develop into a six-time All-Star — and never won the pennant, let alone the World Series.

    @Hford89: Good call on Omar Moreno.

    @Rich: I agree that, at the time, the trade paid immediate dividends. But when you look back almost two decades later, I believe you can make a correlation between that trade and the 18 consecutive losing seasons that followed Barry Bonds’ departure. The Pirates went for broke to win a World Series, failed to win the pennant and then just went broke.

  9. jpg says:

    Did you forget about Matt Morris?

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