1) Rangers draft David Clyde and immediately promote him to the majors
Show of hands: who thinks it’s a good idea to pluck a newly drafted high school pitcher—even the number one pick in the draft—and throw him directly into the fire of the major leagues?

Anyone? OK, anyone besides Bob Short?

Fresh off a move from DC to Texas and faced with dismal attendance in Arlington, Short decided to draft the Houston high school phenom David Clyde with the first pick in the 1973 draft. Nothing out of the ordinary there, but what happened next was anything but ordinary. After signing Clyde to the largest draft bonus in history to that point, the Rangers decided to boost their gate by letting Clyde pitch two starts before heading to the minors.

He pitched 5 innings in his debut, striking out eight but walking seven(!). Somehow he managed to escape, allowing only two runs, and more importantly, Texas had their first ever sellout. In his second start, he pitched better, and the team drew over 30,000 again (this was a team that averaged 7,000 fans a game when Clyde wasn't starting). The revenue provided the impetus to forego the plan to send Clyde to the minors, and his performance was good enough for a 105 loss team to justify keeping him up.

Unfortunately for both the Clyde and the team, things went downhill from there. He slumped to finish the season with an ERA just over 5, and only 8,000 fans showed up for his final start. He didn't pitch much better in 1974 before succumbing to arm injuries in 1975. After three seasons in the minors, he was traded to Cleveland in 1978, where he pitched well for one season before being demoted again and fading from view.

Surprisingly, this experiment didn't turn out too well. Now who could have seen that coming? —Dan Turkenkopf

2) Indians sign Wayne Garland to a 10-year, $2.3 million contract
In today's game, an average player with enough service time to have arbitration rights usually makes a salary of at least $2.3 million. While $2.3 million is a large sum of money to the common man today, it was considered unthinkable in baseball back in 1977. That is why the Cleveland Indians rocked the sport when they signed pitcher Wayne Garland to a 10-year, $2.3 million contract during the 1976-77 offseason, the first winter that featured full-scale free agency in Major League Baseball.

Garland had compiled a 20-7 record for the Orioles in 1976 with a 2.67 ERA in 232 innings as a 25-year-old. The woebegone Indians, who hadn't been to the postseason in 22 years or sniffed contention since 1959, decided they would make a splash in free agency by signing the right-hander. Garland tore the rotator cuff in his pitching shoulder early in the 1977 season but did not tell anyone because he felt the pressure of trying to live up to his record contract. He labored through 292 innings and 21 complete games, going 13-19 with a 3.60 ERA. Garland finally succumbed to the pain in 1978 after making six starts. He had open surgery—arthroscopic procedures were just in the developmental stages then—and returned for the start of the 1979 season, but he was never the same. He was released in 1981, ending his five years with the Indians with a 28-48 record and a 4.51 ERA. —John Perrotto

3) Yankees sign Carl Pavano to a four-year, $39.95 million contract
When the topic of disastrous signings is brought up, the one that Yankees fans will immediately think of is Carl Pavano. In the aftermath of the 2004 ALCS, the Yankees looked to bolster their rotation in the offseason as they were faced with bringing back just Mike Mussina and a 40-year-old Kevin Brown. Meanwhile, Pavano hit free agency after a fantastic 2004 season with the Marlins in which he threw 222 1/3 IP with a 3.00 ERA (137 ERA+), 1.17 WHIP, and a 3.54 FIP. He signed with the Yankees for four years and $39.95 million with a $13 million club option for the fifth year. Throw in the fact that Pavano was being heavily courted by the Red Sox, and it seemed (at the time) that the Yankees had a steal on their hands. Safe to say, it did not turn out that way for Pavano and the Yankees.

Over the course of the contract, he pitched in only 142 2/3 innings (26 games) with a 5.00 ERA and a WHIP of 1.46, good for a grand total of 0.4 WARP. His inability to stay on the field made him a whipping boy in the New York media as well as in the Yankees clubhouse. In his first season, he missed the final three months with a shoulder injury. He followed that up by not making a single major league start in 2006, missing time due to a bruised buttocks and later breaking ribs in a car accident. After starting for the Yankees on Opening Day 2007, he would later go down with an elbow injury that required Tommy John surgery. As the time on the DL piled up, he was mocked relentlessly by the NY papers—who called him the “American Idle”— and Mike Mussina, who told GM Brian Cashman in 2006 contract negotiations, “You’re not paying me less than Carl Pavano.”

After his contract mercifully ended in 2008, Pavano signed with the Twins, which allowed the Yankees to exact a semblance of revenge against him in the 2009 and 2010 playoffs. Pavano gave up 6 runs in 13 innings against his former team and lost both starts. While the signing didn’t cripple the team like some other signings being discussed (it is the Yankees, after all), the mere mention of Pavano brings out the ire of New Yorkers and remains one of the few times the Yankees wish they had lost to the Red Sox. —Sam Tydings

4) Astros sign Carlos Lee to a six-year, $100 million contract
For teams lacking the financial resources to paper over a bad decision, the most disastrous deals have a ripple effect, casting a shadow of opportunity costs and limited financial flexibility that lingers for years. A year removed from their only World Series appearance, the Astros locked themselves into such a deal after the 2006 season, signing free-agent left fielder Carlos Lee for a cool $100 million. The six-year contract covered Lee’s age 31 through 36 seasons, a considerable gamble to make on a player with below-average skills in the field and on the bases.

Not surprisingly, Lee’s defense and baserunning have deteriorated. Though he has hit well enough to justify a place in the lineup every day, Lee has delivered an underwhelming return of just 5.1 Wins Above Replacement Player at a cost of nearly $80 million thus far. At no point has he provided the premium-level production to match his salary. For the privilege, Houston gave up its first-round selection (17th overall) in the 2007 draft (plus the loss of its second-rounder, forfeited the same day when the Astros signed Woody Williams). The Lee deal was not the only cause of the Astros’ downward spiral, but it certainly accelerated the slide. —Jeff Euston

5) Padres acquire Randy Myers from Blue Jays for Brian Loyd
In August 1998, in one of his few missteps as general manager of the San Diego Padres, Kevin Towers put in a waiver claim for Toronto Blue Jays left-hander Randy Myers. Towers intended to keep the Atlanta Braves—whom he erroneously believed had interest in the veteran reliever—from acquiring Myers for the stretch run and beyond.

The Padres and Blue Jays subsequently worked out a deal in which minor-league catcher Brian Loyd headed to Toronto. A 1996 Olympian and fifth-round pick of the Padres out of Cal State Fullerton, Loyd was batting .305/.401/.409 at High-A Rancho Cucamonga in the California League at the time of the trade. Those are nice numbers, but he was 24 years old.

Myers was 35 and, as it turns out, very near the end of his line. He also had $13.58 million remaining on his contract, so the Blue Jays were happy to take anything for him.

Myers worked 14 1/3 innings during the 1998 regular season for San Diego and three more in the postseason. He never pitched after that, his career already over before June 1999 rotator cuff surgery made it official. Myers cost the Padres more than $6 million in 1999 and again in 2000. They paid him a little more than $783,000 per inning, during which he compiled a lofty 6.75 ERA.

Towers spent the 1998-1999 off-season trying to unload Myers, but none of the reported potential suitors would touch that contract. As Towers told the New York Times in February 1999, “That one I will work on until I go to my grave.”

Loyd never reached the big leagues—retiring in 2003 after 536 minor-league games—but he also never hamstrung his team's ability to compete in the free-agent market. Towers still hasn't found a taker for Myers, although in May 2003 the Padres recouped some of their losses when they settled a lawsuit with Lloyd's of London stemming from the insurance carrier's failure to compensate the ballclub for Myers's arm ailments. —Geoff Young

5) Cubs sign Milton Bradley to a three year, $30 million contract
Jim Hendry’s credit card approach to roster building reached its limit in 2008 when the Chicago Cubs were not only the best team in the National League but the winningest Cubs team since Operation Crossroads. However, a quick playoff exit left the team scrambling for answers, and Hendry landed on precisely the wrong one when he signed Milton Bradley to a three-year, $30 million contract. Even setting aside questions about Bradley’s health (both mental and physical) and his reputation as a clubhouse cancer, what the enigmatic outfielder was likely to provide between the lines was unlikely to fix the problems his signing was purported to address.

The Cubs were looking for a left-handed bat to help balance their lineup—a problem that the media had lit upon as the explanation for two successive playoff sweeps. The switch-hitting Bradley, however, had always been weaker from the left side. The Cubs needed to replace the lightning-in-a-bottle production of superannuated center fielder Jim Edmonds; Bradley could only play a corner, thereby transforming Kosuke Fukudome from a defensive asset in right to a liability in center. Mostly, though, the Cubs needed a missing piece to finally push them over the top; marketed that way, Bradley was probably less equipped to shoulder the burden of a century of failed expectations than any player in baseball. It was no surprise that a slow start for both player and team led to boos, recriminations, charges of racism, clubhouse fights, banishment, and all the other trappings of a relationship gone disastrously wrong. The epitaph for Bradley’s brief tenure in Chicago was a straight-up trade for the desiccated remains of Carlos Silva; the biggest indictment of Bradley’s stay is that the Cubs were pleased with that return. —Ken Funck

6) Angels trade Mike Napoli and Juan Rivera to Blue Jays for Vernon Wells
In most cases, teams that acquire players who underperform take a moderate financial licking and keep on ticking. However, most disastrous deals don’t cost the clubs that make them what amounts to a sum greater than the GDPs of some 120 countries. The same can’t be said of a January swap orchestrated by the Angels, however, who sent Mike Napoli and Juan Rivera to Toronto for the privilege of picking up all but $5 million of the $86 million left on 32-year-old outfielder Vernon Wells’s tab.

Wells’s replacement-level play hasn't been worth a penny this season, dollars-per-WARP-wise, let alone the $23 million he's making; as I wrote in yesterday’sTransaction Analysis, his .236 OBP is like one of those optical illusions you have to stare at for a while from a variety of angles and distances to comprehend. Alex Gonzalez is the only other player to have posted a lower single-season OBP in at least 400 plate appearances since 1990—and he was a 23-year-old shortstop when he managed only a .229 mark in 407 trips to the plate in 2000, not a left fielder paid to produce like he did in his prime. Even judged by distance below league average, Wells’s OBP is worse than those of only a handful of players over the past two decades.

Couple that woeful return on investment with the opportunity cost of the four-plus wins Napoli is on pace to accrue for the Rangers (as current Angels catchers combine for a .194/.260/.300 line), and this deal could end up costing the Angels something in the neighborhood of $100 million: a staggering sum. Of course, it’s too soon to write Wells off as a total loss; he’s alternated above-average and below-average seasons since 2004, and if that trend continues, the Halos could still salvage some value from the swap. Still, with Peter Bourjos establishing himself as an attractive option, Mike Trout on the precipice of a regular role, and both Torii Hunter and Bobby Abreu under contract for 2012, Wells might find himself rendered redundant— a process that may already have begun—even if his bat bounces back. Heavy hangs the head that endorsed this deal in the Angels front office. —Ben Lindbergh

7) Mets sign Kaz Matsui to a three-year, $20.1 million contract
Few potential outcomes of Kaz Matsui’s first major league at-bat could have raised expectations for the Mets’ new shortstop higher than they had already been built during the offseason.

In December 2003, the Mets signed Matsui to a three-year, $20.1 million contract and announced that Jose Reyes—coming off of a 6.3 UZR season—would slide over to second base (only a year after the Mets shipped Rey Ordonez off to the Devil Rays in order to make room for Reyes at short). In nine seasons with the Seibu Lions, Matsui had earned four Gold Gloves as well as an MVP award while hitting over .300 and averaging more than 30 steals per year. He’d also exhibited impressive power, socking 130 home runs from 1999-2003.

On top of his own achievements, the stateside accomplishments of two former NPB superstars, Ichiro Suzuki and Hideki Matsui, served to heighten expectations. Ichiro had spent three years with the Seattle Mariners and was among the game’s most exciting players while Matsui finished four points shy of Angel Berroa in the American League Rookie of the Year balloting in 2003.

Kaz Matsui stepped into the box for his first major league at-bat against Russ Ortiz on April 6, 2004 and promptly ripped the first pitch he saw for a solo home run, giving the Mets a 1-0 lead. He finished the day 3-for-3 with a pair of doubles, a couple of walks, and three runs batted in, not to mention a .272 WPA (his third-highest single-game performance of the year).

After a debut of that magnitude, the expression “it’s all downhill from there” would certainly apply in most cases. For Matsui, however, that hill quickly turned into a cliff, and the goodwill earned on Opening Day was quickly forgotten. He finished his rookie season hitting a respectable .272/.331/.396 but drew the ire of fans for his less-impressive-than-advertised defense and, given his previous successes in Japan, relatively underwhelming performance at the plate. In 2005, the Mets shifted Reyes back to short and started the year with Matsui playing second base. Again, he launched a home run on Opening Day, but, though his defensive shortcomings weren’t as pronounced at the keystone, his bat failed to come around. By the end of May, he was sharing time at second base with Miguel Cairo and Marlon Anderson en route to a .255/.300/.352 season.

The Mets dealt Matsui to Colorado for Eli Marrero in June 2006, and he enjoyed some success with the Rockies, leading to a three-year, $16.5 million contract with Houston prior to the 2008 season. His OPS for each of those three seasons with the Astros: .781, .659, .352. He returned to Japan for the 2011 season and recently collected his 1,500th career hit as a member of the Rakuten Eagles.

Matsui was the first Japanese superstar position player to come to the major leagues and fail (sorry, Tsuyoshi Shinjo), and it is unfortunate for him that he chose to prove himself at the toughest level in the world’s largest and most tenacious media market. Despite the lampooning he received in the U.S. for his failure to produce to expectations, Matsui is inarguably the best infielder to come over from Japan, and he challenges Kosuke Fukudome as the most productive Japanese position player since Ichiro and Hideki Matsui made their debuts nearly a decade ago. —Bradley Ankrom

8) Blue Jays sign B.J. Ryan to a five year, $47 million contract
The week that he signed B.J. Ryan to a five year, $47 million deal in November 2005, J.P. Ricciardi defended the terms. "We've already signed Roy Halladay to a four-year contract. To me, there's very little difference between four years and five years," he said. Nifty maneuver (Canadian exchange: manoeuvre), focusing attention on the difference in years rather than the difference in products. "Spend three hours with Matt Holliday's moth flying around in my skull? Well, I spent two hours watching secret, unaired episodes of Freaks and Geeks. To me, there's very little difference between two hours and three hours." Ryan's best Roy Halladay impression would last just one year, and over the rest of the contract the Jays would get saves from Jeremy Accardo ($392,000), Scott Downs and Jason Frasor ($5.2 million as a tandem), and Kevin Gregg ($2 million) instead. —Sam Miller

9) Tigers acquire Juan Gonzalez from Rangers
The summer of ‘99 had ended, Historic Tiger Stadium had closed its doors for the last time, and Ernie Harwell had turned off the lights at the Corner of Michigan and Trumbull. The Tigers were moving to spacious Comerica Park, and general manager Randy Smith was looking to make a “splash.” The splash he made nearly crippled the team as he traded away the farm for Juan Gonzalez. The only thing that saved the Tigers was the ego possessed by Gonzalez, which prevented him from taking the Tigers’ record breaking 8 year, $140-million contract extension.

The disaster wasn’t in the trade itself but rather in the assumption by the Tigers GM that Gonzalez was ready to sign the extension at his introductory press conference and even further that Gonzalez, with the GM as his puppet, made a mockery out of his time in Detroit. The worst part of it all was that Smith believed his offer for Gonzalez—who would be 38 by the end of the contract—was a fair deal for both sides: "This guy is one of the best players in the game. His consistency is phenomenal. He's always been productive. We think this is a good offer for a great player." It was quite lucky that Gonzalez didn’t believe it was fair and turned it down."When you have a player of this caliber—on his way to Cooperstown—he's going to be expensive," Smith said. "But we think he's worth it, especially if he stays consistent."

The mockery of the Tigers continued as they tried to trade the depressed slugger at the deadline to the Yankees for Drew Henson only for Gonzalez to reject the deal and force the Tigers to keep him for the remainder of the year. Mercifully, the Juan-Gone era in Detroit would end early due to an injury that summer. The once “future Hall-of-Famer”, instead of making $140-million until age 38, would be out of baseball at age 35 as a cellar dwelling Kansas City Royal. Randy Smith almost killed the Detroit Tigers with Juan Gonzalez; thankfully Juan Gone was too egotistical to let that happen. —Adam Tower

10) The Royals sign Mark Davis to a four-year, $13 million contract
It’s always a good thing when a team adds a Cy Young winner in his prime, right? As it turns out, not every time. Southpaw Mark Davis had pitched well enough in the minors to reach the majors at age 19, but he had subsequently failed to establish himself as a starter and drifted from the Phillies to the Giants to the Padres. The Giants shifted him to the bullpen, where his command of what became an outstanding curveball dramatically improved. In 1985, his first season in the pen, his strikeouts per nine jumped from 6.4 to 10.3. Moving to the Padres in 1987’s controversial Kevin Mitchell deal, he became the closer in 1988. The next season, he dominated the league, saving 44 games in 48 chances with a 1.85 ERA. There were better seasons by starters that year (Orel Hershiser, Greg Maddux), but none of them had won 20 games. The Cy Young voters hadn’t yet learned to see through won-lost records so they defaulted to Davis.

Davis collected his award and hit the free agent market, hotly pursued by the Phillies, Angels, and Yankees, all of whom had made higher total-dollar offers than the ultimate winners, the Kansas City Royals. This was in the days when the Royals were still a serious baseball team and gave out big contracts. They won Davis by offering the highest annual value of any bidder, $3.25 million a year over four years. “Some guys don't want the challenge of New York,” groused George Steinbrenner, who had offered a five-year deal. In signing Davis, general manager John Schuerholz did something unprecedented, putting the National League’s Cy Young winner on the same staff as that year’s American League winner, Bret Saberhagen.

Alas, it did not work out, though Schuerholz was off to the Braves before the full impact could be felt. Davis fell apart in 1990. The command of the curve vanished, and his confidence went along with it. He suffered from a hairline fracture of a finger on his pitching hand and elbow tendinitis. His walks jumped from 3.0 per nine to 6.8 and the ball began flying out of the ballpark. He was deposed as closer by May, and in desperation the Royals tried him as a starter. That didn’t work either. The Royals even hired Davis’s old San Diego pitching coach, but he couldn’t help—the lefty’s command was gone forever. Ever the good sport, Schuerholz traded a used-up Juan Berenguer to the Royals for Davis’s contract in 1992, but the damage had been done. The Royals had gone 92-70 in 1989, finishing in second place. With Davis’s help (and that of another misguided Schuerholz-signed Davis, Storm), they went 75-86. From that day to this one, they have never come close to another 90-win season.—Steven Goldman

11) Erik Bedard to the Mariners

Rumors of Erik Bedard being dealt away from the Orioles swirled throughout 2008 until a trade was consummated that sent him from the Orioles to the Mariners. The Mariners were reportedly looking for another frontline starter to pair with Felix Hernandez. Bedard was fairly useful while healthy, but he suffered shoulder injuries, including a torn labrum and related complications, which limited him to 164 innings across 2008 and 2009 and caused him to miss all of 2010. In that context, this may not seem like a disastrous acquisition.

The problem is that the Mariners gave up a bundle of talent to the Orioles, especially Adam Jones, a player many thought to be more valuable than Bedard on the day the trade was made, along with several others. So far Jones has amassed 11.8 WARP with Baltimore, and in addition to having the rest of this season to add to that total, the club has two more cost-controlled years with Jones in 2012 and 2013.

In addition to Jones, the Orioles acquired Chris Tillman, Kam Mickolio, George Sherrill and Tony Butler. Jones remains the big ticket but the other components have provided value to the Orioles as well, both on the field and in trade. The silver lining for the Mariners, if there is one, may lie in the acquisition of Trayvon Robinson at the deadline this July in a deal that sent Bedard to Boston. Robinson profiles as a regular outfielder from here on out and has already dazzled Seattle fans with his defensive prowess. I suppose you could also argue that the trade helped prompt the installation of a new management regime in Seattle, which many fans welcomed. If you tally up the WARP coming and going, the net effect for the Mariners to date includes acquiring Bedard (+4.1) and losing out on Jones (-11.8), Sherrill (-1.1), Tillman (-1.1), Mickolio (-0.3), and the acquisition of Reynolds (-0.9), for an approximate impact of over 11 wins over the course of the past four seasons. Of course, this seems likely to continue to get worse for the Mariners, as Jones is a burgeoning star and several of the other current Orioles—especially Tillman and Reynolds—seem likely to contribute value as well, for at least a couple more years.—Ben Murphy