30) 1927-28 Pittsburgh Pirates
Moves: Traded Kiki Cuyler for Sparky Adams and Pete Scott. Traded Vic Aldridge for Burleigh Grimes. Sold Joe Cronin. 33.6 WAR lost.
In 1927, the Pirates benched their Hall of Fame center fielder, who was still in the prime of his career, and still made it to the World Series (where they were dismantled by the Yankees). It was pretty amazing, and by the end of the season, nobody really understood why. Cuyler felt it was because he had been misrepresented in the press and that he had been unfairly maligned by his manager, though he purported to feel no ill will after the season was over, "I think I have played for the last time in a Pirate uniform. Not because I don't wnat to play in that uniform, but because my employers, I have heard, have other plans." Indeed, the Bucs traded Cuyler for a couple of middling players.
Amazingly, the response from around baseball was that the Pittsburgh had won the trade. John McGraw told reporters, "I think the Pirates got all the better of the deal. Adams is a dangerous ball player, always getting on base, and with a hard-hitting team like the Pirates behind him, he will bother pitchers more than ever. There is a question whether Cuyler is as good as he used to be. He failed in the pinches many times last season." Yankees GM Ed Barrow agreed, "The Pirates seem to have received a lot for nothing. They have fortified themselves where they needed help and where a glaring weakness developed in the world series, and they lost no strength because they would not use Cuyler."
In 1928, Cuyler would post a 117 OPS+ and lead the NL in stolen bases, while his Cubs jumped from 85 to 91 wins. The Pirates dropped from 94 to 85 victories and would finish behind the Cubs in 4th place. Adams would last another season in Pittsburgh, but Scott was gone. Cuyler would re-discover his stroke and be one of the most valuable players in the National League in 1929 and 1930.
Meanwhile, nobody noticed when the Pirates sold a little-used backup infielder back to the minors. But Joe Cronin would be picked up by the Senators later that year and provide them with 25.0 wins above replacement over the next five years.
29) 1971-72 St. Louis Cardinals
Moves: Traded Steve Carlton for Rick Wise. Traded Jerry Reuss for Lance Clemance and Scipio Spinks. 37.4 WAR lost.
The trade of Steve Carlton has been dissected a number of times, and the Cardinals always come out looking fairly ridiculous. The move came on orders from team owner Augustus Busch, who had decided he’d had enough of negotiating with Carlton at contract time. So Busch ordered him deat. The Cards did manage to get a good pitcher out of it in Wise, but not nearly as good as Lefty. Rob Neyer estimates the Cardinals would have won the AL East in 1973, 1974 and 1981 if they’d held on to their ace.
What’s really interesting (and The Common Man doesn’t know if anyone’s made this connection before), is that something really strange was going on in the 1971-72 offseaon, as several teams made absolutely unconscionable deals. Four of them (the Cardinals, Red Sox, Mets, and Astros), as you will see, end up on this list. Whether that’s because of the labor unrest that Spring or not, teams dumped superstars readily that offseason, and got back very little in return. Maybe somebody spiked the punch at the Winter Meetings.
28) 1920-21 Boston Red Sox
Moves: Traded Waite Hoyt, Wally Schang, Harry Harper and Mike McNally for Del Pratt, Muddy Ruel, Hank Thormahlen, and Sammy Vick. Traded Harry Hooper for Shano Collins and Nemo Leibold. 39.1 WAR lost.
The Red Sox big mistake in the winter of 1919-20 gets all the press (and, yes, it will appear on this list, settle down), but this was pretty bad too. Hoyt was just 21, and a virtual unknown when the deal went down. Harper was the big pitching get for the Yankees, as he had been a terrific pitcher on some bad Senators and Sox teams, and was only 25. But he got hurt and would only pitch 8 games for the proto-Bombers. Hoyt, on the other hand, whould throw in 365 more contests, and win 157 of them for the Yanks. And Schang was tremendous catcher, who had had a 126 OPS+ in his three years in Boston.
The real prize for the Sox was Pratt, a slugging 2B who was also a good fielder. The strange thing was, the Sox had some doubt about whether Pratt was going to play in 1921. The Reading Eagle reported, "He signed a contract as athletic coach with a western university [Michigan] at the concusion of last season, and declared his intention to quit baseball. The Yankee management, however, today expressed confidence that Pratt will be ready to get into the game when the 1921 season opens." Pratt was lured back just before the season started, and gave the Sox two excellent years before being traded again. But Ruel was a disappointment for them, and Thormalhlen and Vick did nothing.
27) 2007-2008 Arizona Diamondbacks
Traded Carlos Quentin for Chris Carter. Traded Alberto Callaspo for Billy Buckner, Traded Brett Anderson, Chris Carter, Aaron Cunningham, Dana Eveland, Carlos Gonzalez, and Greg Smith for Dan Haren, Traded Jose Valverde for Chris Burke, Juan Gutierrez, and Chad Qualls. 27.1 WAR lost (so far).
Despite being outscored, the 2007 Arizona Diamondbacks won 90 games and the NL West crown in one of the flukiest seasons of all time. So, of course, they decided to double down on 2008. First, they traded the disappointing Carlos Quentin to the White Sox, where he promptly became an MVP candidate. Then, they took the prospect they got in that deal (Chris Carter), and traded him and what was left of their farm system to the Oakland A’s for Dan Haren. Haren was terrific, but so was the package they sent north, which included 2010 MVP candidate Carlos Gonzalez and one of the best young arms in the Majors, Brett Anderson. The team predictably slipped back to 82 wins, and finished two games back of the Dodgers.
26) 1971-72 San Francisco Giants
Moves: Traded Gaylord Perry and Frank Duffy for Sam McDowell. Lost 39.1 WAR.
It's hard to blame the Giants for making this deal. McDowell, in his prime, was a better pitcher than Perry (although Perry was more durable; that guy was iron). He had MUCH better stuff, and was 4 years younger when this trade went down. And Duffy wasn't much, just a slick fielding SS who had never had an OPS above .675 in three minor league seasons. McDowell, famously, was a very hard drinker, and had not endeared himself to the Indians in 1971 by asking to be released from his contract after Commissioner Bowie Kuhn negated some of the incentive clauses for games won and innings pitched (but not the contract in total, since it was the middle of June). The Indians threatened to sue McDowell, and he backed down.
That offseason, they struck the bargain with the Giants, who were very pleased. Perry allegedly showed up for camp "in the best shape he's been in four years" (Hi, Craig!), and advocating acupuncture that "helped him get rid of adhesions in his left shoulder last spring." In his Spring debut, McDowell was tagged for eight runs in the first inning against the Cubs, and things didn't get much better. McDowell's ERA would wind up 18 percent below the league average, and he would only win 10 games in 164 innings. Perry, meanwhile, won the AL Cy Young award with a 1.92 ERA in 342 innings, and 24 wins for a 5th place club. And Duffy settled in as the Tribe’s starting SS until 1977.
25) 2009-10 Seattle Mariners
Moves: Lost Adrian Beltre. Signed Chone Figgins. Traded Brandon Morrow for Brandon League and Johermyn Chavez. Traded Carlos Silva for Milton Bradley. Traded Bill Hall for Casey Kotchman. Signed Eric Byrnes and Erik Bedard. Traded JC Ramirez, Phillippe Aumont, and Tyson Gillies for Cliff Lee. 7.7 WAR lost so far.
The Mariners' moves weren't so bad in isolation. They felt they had seen enough of Beltre that they didn't want him back, but he ended up signing a short, team-friendly deal in Boston. Similarly, the signing of Figgins was defendable, and the trade of Silva brought back a player with some upside. Morrow had underwhelmed as a starter and reliever. And, of course, Cliff Lee was coming to town. The biggest trouble was the high expectations that these moves created, both in Seattle in across the rest of the baseball world. Seattle was considered a potential dark horse, and every move by its darling GM, Jack Z, was praised.
But then reality set in. Silva bounced back nicely for the Cubs while Bradley was an unmitigated disaster in his new home. Similarly, Bill Hall revitalized his career in Boston, while Casey Kotchman couldn't play with that fork sticking out of his back. Bedard was out for the entire season. Byrnes was too far gone to be of any use. Morrow blossomed into an impressive young starter. And Beltre enjoyed one of the best seasons of his career while Figgins floundered. Lee was great, but was shuffled off in July in a more realistic attempt to create the next competitive Mariners squad. The M's remain a warning about the perils of groupthink, and the importance of impartiality. Having a crush on a GM isn't healthy for good analysis.
24) 1989-1990 Kansas City Royals
Moves: Signed Storm and Mark Davis. Re-signed Frank White and Willie Wilson. Traded Charlie Leibrandt and Rick Luecken for Gerald Perry and Jim Lemasters. Signed Richard Dotson. Traded Jose de Jesus for Steve Jeltz. 17.6 WAR lost.
The free agent acquisitions of Storm and Mark Davis are still, 20 years later, among the greatest of Free Agent busts. The Royals, after winning 92 games in 1989, felt like a big market club, and spent like it, ending up with the largest payroll in Major League Baseball. They signed Storm for three years and $7 million, and NL Cy Young winner Mark for four years and $13 million. Between the two pitchers, Kansas City netted -1.1 wins above replacement. The Charlie Leibrandt trade was just as disastrous, however. Perry was a 1B with speed, but no patience and no power, who had hit an empty .300 in 1988. The Royals thought they could alternate him and George Brett at 1B and DH. But Perry, predictably, was awful, hitting .254/.313/.361, with just 8 homers. Leibrandt, who had suffered through a tough '89 (likely because of bad luck and because he was hurt), bounced back over the next three years with the Braves, winning 39 games and helping them get to two World Series.
The Royals never really recovered from a psychic standpoint. Learning that the Free Agent market is fraught with peril, they largely avoided it over the next several years, considering themselves too small-market to pursue the players they needed. They have only finished above .500 three times in the last 20 years, and their highest win total has been 84.
23) 2000-01 Colorado Rockies
Moves: Signed Mike Hampton and Denny Naegle. Signed Ron Gant. 6.9 WAR lost.
In the first eight seasons in Denver, nobody could quite figure out how to build a pitching staff at altitude. They tried curveballers (Daryl Kile), but that didn't work. They tried to build a strong bullpen, but the starters all fizzled. In his second year as the GM, Dan O'Dowd thought he had the answer: sinkerballers. Rockies pitchers were giving up home runs at amazing rates, and sinkerballers would keep the ball in the park with their heavy fastballs. So O'Dowd invested 6 years and $108 million in Mike Hampton and 5 years, $51 million in Denny Neagle. The plan went awry. Hampton's fastball wouldn't sink in the light Denver air and he tried to make adustments. Nothing worked. After two years and a 5.75 ERA, Hampton was traded, with the Rockies agreeing to pick up half of the rest of his contract. Neagle was also an incredible bust, finishing with a 5.57 ERA before an elbow injury knocked him out of all of 2004. He was caught with a prostitute that winter, the Rockies tried to void his contract, and he never pitched in the Majors again.
While the Davis deals seemed to destroy the Royals' psyche, these free agent busts destroyed the Rockies' balance sheet. Saddled with contracts they simply couldn't unload, the Rox were unable to build another successful team until 2007.
22) 1997-98 Tampa Bay Devil Rays
Moves: Traded Bobby Abreu for Kevin Stocker. Traded Dmitri Young for Mike Kelly. Signed Wade Boggs, Paul Sorrento, Dave Martinez, John Flaherty, Wilson Alvarez, and Roberto Hernandez. Purchased Fred McGriff. 19.4 WAR lost
No expansion team expects to emerge, fully formed, from a clam shell as a bonafied contender, but it's also hard to imagine a team misfiring so bad as the Devil Rays did before they had even played a Major League game. Prior to 1997, Bobby Abreu was the #38 prospect in baseball, according to Baseball America. He had a mediocre season at AAA, but had held his own in 210 plate appearances for the Astros as a 23 year old, and was undoubtedly still a good young hitter.
So when the Rays drafted him in the third round of the expansion draft, they had an opportunity to take a potential everyday player who could be a cornerstone for their young franchise. Instead, they traded him for a 28 year old shortstop, Kevin Stocker. As Rob Neyer wrote in his Big Book of Baseball Blunders,
"Could Devil Rays general manager Chuck LaMar have guessed that Stocker would go in the tank immediately after joining the new franchise... Hardly. Could LaMar have guessed that Abreu would quickly become one of the top right fielders in the major leagues? No, not really. But should he have known that Abreu might become a star and Stocker almost certainly would not? Should he have known that it's lmost impossible to win without stars? Yes, and yes. On what was essentially the first meaningful day in franchise history, LaMar made a terrible decision that served as an ill omen for what would follow."Mike Kelly was a super-athlete who hadn't yet been able to put together all his tools, except for a short half-season stretch in Cincinnati. Tampa bit, sending the useful Dmitri Young to the Reds for him. in 106 games, Kelly posted a .295 OBP and was never heard from again. Boggs was a legacy signing and a publicity stunt, a chance for the Rays to buy some history (along with, allegedly, Boggs' hat in the Hall of Fame). Flaherty was terribly miscast as a starting catcher. Alvarez signed a big five-year contract, got hurt every single year, even missing both 2000 and 2001. Sorrento, once a big power threat, was done. Martinez was on his last legs, and couldn't play CF anymore. Hernandez did well, but how often does a 95-100 loss team really need a closer? And The Crime Dog didn't embarrass himself, but that's about it. Frankly, it's hard to imagine what the plan was here, except to maybe try and win 81 games in their inaugural season. Instead, they wouldn't finish above .500 until 2008.
21) 2002-03 Minnesota Twins
Moves: Released David Ortiz and Casey Blake. Traded Javier Valentin and Matt Kinney for minor leaguers. Signed Kenny Rogers. 36.4 WAR lost
The Twins had just come out of their eight year sojourn into baseball’s small-market wilderness and won their first AL Central crown, when they inexplicably dumped David Ortiz. The massive DH and 1B had hit .272/.339/.500 the previous year and had shown prodigious power. But his willingness to take a walk, reluctance to hit to the opposite field, and poor defense left him out of step with the rest of the Twins’ orthodoxy. So they released him. Just released him. They gave him away for nothing. The Red Sox pounced, and Ortiz would hit 208 homers over the next five years while serving as their primary DH. Big Papi became an icon, MVP candidate, and postseason hero. The Twins’ DHs never posted an OPS+ over 116 (while Papi averaged 156), and the Twins continually got swept out of postseason.
Not as dramatic, the release of Casey Blake is also somewhat troubling. Blake was 28, and had had several strong seasons at AAA (his career AAA line is .290/.373/.482) under his belt, but couldn’t get past Corey Koskie, who was entrenched at 3B. But the Twins had a hole in RF or as Jacque Jones’ platoon partner in LF that Blake would have fit into nicely. Instead, the Twins let him walk. He went to Cleveland, where he became a solid 3B and RF for the next several years. The Twins have had a nice run since 2002, but it likely would have been much better with both Ortiz and Blake in the fold.