Not Every Trade Worked

08/08/2006 11:12 AM ET
By Jonah Keri / Special to

Brian Cashman did not panic at the trade deadline.(AP)

When the Yankees fell short of a World Series title for the fifth straight season in 2005 — an eternity in the Bronx — most observers expected the team to reload in the offseason. Given one of the weaker free-agent classes in recent memory, the smart money had general manager Brian Cashman calling around and dangling the best young players in the Yankees' system. After all, trading top prospects for aging, if still productive, stars has been a Yankee hallmark for decades.

But along the way, a funny thing happened. Which is to say, nothing happened. At least, not to the Yankees' best prospects.

Of course, the Yankees made an offseason splash by signing Johnny Damon. But he was their only big-ticket free-agent signing. As the season progressed, injuries to Gary Sheffield, Hideki Matsui, Robinson Canó and others seemed to sound alarm bells in the Bronx. With the Red Sox an able rival again this season and the wild-card race fiercer than ever, a trade by the All-Star break seemed a near certainty. Still, the Yankees stood firm.

Ah, but the trade deadline. That's where Cashman would reach down to the minors, pull out Phil Hughes, José Tábata and company and cash them in for veteran help. Or so we thought.

Instead, the Yankees took advantage of their biggest resource — cash — to do the deal. In trading on-base ace Bobby Abreu and mid-rotation starter Cory Lidle for four B-level prospects, the Phillies looked past their status as the biggest one-team market in Major League Baseball, shrugged off their sparkling new publicly financed stadium and said "tough luck" to their diehard fans. From the Yankees' perspective, they managed to add a top-flight bat and a useful starter, all without relinquishing any top-tier prospects from an underrated farm system that has several. Years from now, we may look back at the Abreu-Lidle deal as the blueprint for all Yankees trades: Taking advantage of teams' willingness to dump salary and give up top talent for second-class farmhands.

If the Yankees do end up shifting to cash-for-talent mode in making deals, it would mark a welcome change from past strategies. As one publication put it:

"…Given their willingness to spend, why don't the Yankees win more often? One reason is their reliance on older players. They have consistently traded away young players who could be so vital to their future for the single player they feel they need right now."

Was this a recent missive in one of the New York papers, a stinging indictment of the end of the Yankees' dynasty 1996-2000 dynasty? Nope. Actually, it appeared in the book "The Baseball Trade Register: Every Trade, Sale, and Free-Agent Signing from 1900 on", by Joseph L. Reichler, published in 1984. Those who forget history are doomed to repeat it, as the Yankees have shown numerous times since that book came out. With that in mind, let's look back at the 10 worst trades in Yankee history, in chronological order:

Jan. 22, 1918: Traded Urban Shocker, Les Nunamaker, Fritz Maisel, Nick Cullop and Joe Gedeon to the St. Louis Browns for Eddie Plank, Del Pratt, and $15,000
Plank was a Hall of Famer who'd amassed 326 wins to that point in his career. He was also 42 years old. Though still effective into his early 40s, Plank would never pitch a game for the Yankees. Pratt was a solid Yankee contributor for three years, including a 1920 season that saw him hit .314. Meanwhile, four of the five players the Yankees gave up never amounted to much.

The Yankees dealt the fifth, Shocker, to St. Louis after manager Miller Huggins was told that his pitcher was being disruptive. Shocker went on to shock the league, developing into one of the dominant starters in all of baseball, including four straight 20-win seasons from 1920 to 1923. The Yankees finally reacquired him before the 1925 season, with Shocker by then well into his 30s. He had some gas left in the tank, though: At age 36 he was arguably the best pitcher on the famous 1927 World Series-winning team, going 18-6.

Feb. 5, 1942: Traded Tommy Holmes to the Boston Braves for Buddy Hassett and Gene Moore
Casey Stengel, then manager of the Braves, said that Yankees farm director George Weiss — a good friend of Stengel's — was doing him a favor by trading him Holmes. That the Yankees had about 472 promising outfielders in their system made the deal seem more palatable. Moreover, they were still trying desperately to replace Lou Gehrig, a string of lamentable first basemen having failed to do the job. In 1941 it was Johnny Sturm, a punchless rookie who put up a Mario Mendoza-like line of .239 batting average/.293 on-base percentage/.300 slugging average. Sturm left for military service, so the Yankees didn't even have his lackluster services. Hassett hit .296 in 1941 and owned a .293 career average, making him seem more attractive as a trade acquisition. This was more than six decades before Moneyball, but deep down the Yankees had to know they weren't getting filet mignon. Hassett hit a grand total of seven homers in his six-year career to that point — albeit in an extreme pitcher's park during his three years in Boston — and rarely walked. He gave the Yankees one pedestrian season in '42, then got called to war and never played in the big leagues again.

And Tommy Holmes? He was just getting started, joining the Braves as a 25-year-old rookie the next season. Holmes went on to play 11 years in the majors, making two All-Star teams, five times finishing in the top 10 in batting average, hitting .302 for his career and doing it with a lot more pop than Hassett, mostly while playing in the tough environment of Braves Field. He also hit in 37 straight games from June 6 to July 8, 1945, and was the only player ever to lead the league in home runs and fewest strikeouts, with 28 homers and nine strikeouts — and 70 walks! — that same season. Even back then the Yankees occasionally rashly traded players before they got a chance to prove themselves.

May 3, 1952: Traded Jackie Jensen, Spec Shea, Jerry Snyder and Archie Wilson to the Washington Senators for Irv Noren and Tom Upton
There's an argument to be made that a trade can only be as good or as bad as the team's performance after the fact. The Yankees were in the midst of the greatest dynasty in professional sports history, including five straight World Series titles from 1949 to 1953 under Stengel. They followed that stretch with nine pennants and four World Series crowns in the next 10 seasons. So it's tough to point to any one player, no matter how good, and say for certain that he would have changed things for the better. How much better could things get?

Noren, the Yankees' chief acquisition in the deal (Upton never played a major league game after the trade), was no stiff. His .319/.377/.481 line in 1954 ranked him among the league's best that year. But he was a part-time player the rest of his career, and never again played that well.

The Yankees lost a gem when they dealt the 25-year-old Jensen to the Senators. Flush with young outfielders, he was deemed expendable as the team sought to load up for another championship run that year. Still, Jensen's early-career performance already portended stardom, with a sparkling .298/.369/.500 mark in part-time duty in 1950 and a solid campaign in '51. Jensen would go on to play in three All-Star Games and win the 1958 MVP. The Senators apparently didn't know what they had either, as Jensen enjoyed most of his best years in Boston. Would the Yankees have won more championships with Jensen still in tow? That's debatable. But he would have looked great in the team photo, if nothing else.

May 16, 1976: Traded Larry Gura to the Kansas City Royals for Fran Healy
In the 1950s, the Yankees practically used the old Kansas City Athletics as a farm system, acquiring Roger Maris and other key contributors from that cash-strapped team for pennies on the dollar. Turnabout is fair play, as the Royals snared Gura for the forgettable Healy. Yes, the Yanks needed a useful backup catcher to give Thurman Munson some much-needed rest. But Healy wasn't that guy, as he hit .251 with no homers in just under two seasons in the Bronx.

The Larry Gura Saga illustrated the downside of having Billy Martin for a manager. Gura went 5-1 with a sparkling 2.41 ERA in eight starts in 1974. Promoted to full-time duty the next season, his 3.51 ERA wasn't as impressive, but was still four percent better than league average. Accounts differ as to why Martin seemed to loathe his lefty pitcher. Some say Gura's low strikeout rates irked his skipper — though no one complained when Tommy John carved up the league later that decade while wearing pinstripes. Either way, Gura went on to a highly successful career in K.C., making up the bulk of his solid 16-year career.

June 15, 1976: Traded Tippy Martínez, Scott McGregor, Rick Dempsey, Rudy May and Dave Pagan to the Baltimore Orioles for Ken Holtzman, Doyle Alexander, Ellie Hendricks, Grant Jackson and Jimmy Freeman
Coming off two World Series titles and six playoff appearances from 1966 through 1974, the Orioles realized they needed to reload by converting some established veterans for younger talent and fueling the next wave of great teams in Baltimore. Luckily for Earl Weaver and company, the Yankees' largesse knew no bounds during the 1976 season. Less than a month after discarding Gura, the Yankees sent a boatload of talent down I-95 in exchange for a package of players they hoped would put them over the top. Martínez would pitch 11 more years, anchoring the Orioles bullpen and making the 1983 All-Star team. McGregor was a mainstay in the O's rotation for years. Dempsey was never a great hitter, but he remained a fixture behind the plate and a dominant defender for the O's for 10 years. May would prove to have a few useful seasons left as well.

This trade deserves a caveat, though, since it did help the Yankees that season. Jackson was lights-out down the stretch that year, flashing a 1.69 ERA and a 6-0 record. The Yankees would lose him that offseason after the Mariners grabbed him in the expansion draft. Alexander would also leave at year's end, for free agency. But the right-hander's 10-5 record and 3.29 ERA helped propel the Yankees to an AL pennant, before the Big Red Machine knocked them off in the World Series. Alexander is also widely recognized for being part of one of the most lopsided trades for any team, when the Detroit Tigers acquired him in 1987 for future Hall of Famer John Smoltz. Both the Yankees and Tigers sacrificed big chunks of their future for Alexander's services, but he came through both times — it wasn't his fault that his team failed to win it all in both cases.

Oct. 21, 1981: Traded Willie McGee to the St. Louis Cardinals for Bob Sykes
After playing in parts of five seasons with the Tigers and Cardinals, Sykes never again played a major league game after this trade. Meanwhile, McGee was about to start a great career. As a rookie in 1982, McGee managed a .296 average, albeit with minimal power and walks. Still, he was a regular on that season's World Series-winning team. He later blossomed into a three-time Gold Glove winner, a four-time All-Star and the National League's Most Valuable Player in 1985.

With every one of his passing achievements, the Yankees would grow to deeply regret the McGee trade — so much so that they tried to emulate the success of McGee and his jackrabbit Cardinals teammates. They acquired Ken Griffey Sr., who turned in 4 1/2 mostly above-average seasons in New York, but was no longer the speed demon he'd been in his 20s. They also picked up Dave Collins, a speedy outfielder with no other useful assets. He was chucked overboard after one disappointing season in 1982. The whole idea was misguided, but management had decided they were going to be the Go-Go Yankees, damn the torpedoes. Every team imitates the winner du jour, regardless of the era. But Yankee Stadium lacked the turf and big dimensions to make the Cardinals' brand of smallball work, not to mention the personnel to pull it off.

Dec. 9, 1982: Traded Dave Collins, Fred McGriff, Mike Morgan and cash to the Toronto Blue Jays for Dale Murray and Tom Dodd
It may seem like we're picking on the Yankees of the 1980s, but really we're not — they just made a ton of awful deals during that decade, several of which didn't make the cut for 10 Worst status. The common denominator for most of them involved the Yankees trading away a great prospect for an over-30 player, hoping to win now at any cost. But as the current Yankee regime has demonstrated, a win-now approach doesn't have to preclude winning later.

In this case, it did. The Yankees headlined this deal by running away from the Dave Collins Experiment. But the plum would turn out to be McGriff, a power-hitting teenager with a promising future, albeit one that was still years from fruition. We know how the story ended for McGriff: 493 career homers, five All-Star Games, All-Star MVP in 1994 and a career worth Hall of Fame consideration. Murray was an erratic pitcher who managed one of his better seasons in '82, crafting a 3.16 ERA in 111 effective relief innings. But with the exception of a few Mariano Rivera rocks of consistency, relievers were, are and will always be fickle creatures, especially those who lack overwhelming stuff and are entering their mid-30s. Murray added nearly a run and a half to his ERA in 1983, tossed a few innings in '84, and was out of baseball soon afterwards.

July 13, 1987: Traded Bob Tewksbury, Rich Scheid and Dean Wilkins to the Chicago Cubs for Steve Trout
After completing this deadline deal with the Cubs, Yankees owner George Steinbrenner supposedly told his manager, Lou Piniella: "Lou, I've won you the pennant. I got Steve Trout." Sources later whispered that what Steinbrenner really said was: "Lou, I need some ointment. I got the gout."

At the time, those within the Yankees organization said that Tewksbury was a pitcher who could win only when all the conditions were in his favor. Tewksbury's low strikeout rate did put a lot of pressure on his defense. But his extremely low groundball rates also kept the ball in the park. His microscopic walk rate forced opponents to swing the bat to beat him. After struggling with the Cubs, Tewksbury landed in St. Louis, where he reeled off five straight seasons with above-average ERAs; in 1992 he put up Cy Young-caliber numbers, going 16-5 with a 2.16 ERA and an amazing total of just 20 walks in 233 innings.

Meanwhile, Trout was a disaster. He posted a 6.60 ERA, and lacking Tewksbury's great control, walked more batters than he struck out. Not surprisingly, the Yankees did not win the pennant. The most ironic part of the trade was that for all the carping about Tewksbury's low strikeout rate, Trout never struck anyone out either. His career K rate? 3.9 per 9 innings. Tewksbury's? 4.0 per 9 innings.

July 21, 1988: Traded Jay Buhner, Rich Balabon and Troy Evers to the Seattle Mariners for Ken Phelps
"How could you have traded Buhner for Ken Phelps?" The line made famous by George Costanza's acerbic dad Frank on Seinfeld could have easily been uttered by any Yankee fan in the 1990s. To his credit, Phelps was a gem in Seattle for more than five seasons, flexing huge power and putting up Ted Williams-level walk totals. Despite a strong minor league track record, Phelps didn't break into the majors until age 25, as scouts feared his long swing, strikeout totals and overall non-scouty gestalt. Even in the majors, the Mariners didn't quite turn him loose, with Phelps topping out at 125 games played in 1986. (Phelps' long stint in the minors and sporadic big league playing time — despite great production whenever he did play — gave rise to the "Ken Phelps All-Star Team." A Ken Phelps All-Star is a player who produces everywhere he goes, but for one reason or another fails to get a fair shot, usually getting left behind in the minors.) Steinbrenner coveted Phelps, daydreaming about the carnage he'd inflict on the league once given an everyday chance to take aim at the short right-field porch in Yankee Stadium. But by the time he hit New York, Phelps was going on 34 years old, his best days behind him.

Meanwhile the Yankees gave up way too soon on Buhner, a player 10 years Phelps' junior who ironically had a very similar skill set, with tons of power and patience mixed with a so-so batting average. The Yankees had previously engineered a heist, having dealt Steve Kemp, Tim Foli, and cash to the Pirates in December 1984 for Dale Berra, Alfonso Pulido and Buhner. But the Phelps deal wiped out most of the benefit of that steal. The man known as Bone went on to become one of the greatest .254 hitters to ever play the game, crunching 310 career homers, gunning down legions of baserunners who dared test his cannon arm and serving as a focal point for some of the best teams in Mariner history.

July 30, 2004: Traded Jose Contreras and cash to the Chicago White Sox for Estéban Loaiza
The only player in Yankees history given a bigger signing bonus than the $6 million Contreras got in 2002 was…Hideki Irabu's $8.5 million payday five years earlier. If that wasn't a bad omen, what is? A dominant pitcher in his native Cuba already in his early 30s (at least) when he signed, the Yankees expected to add an ace when they inked the big right-hander. In his first season, Contreras looked ready to live up to the hype. In 71 innings, including nine starts, Contreras struck out 72, allowed just 52 hits and four homers, and helped carry the team into the playoffs. The next season, he maintained his strikeout and walk rates for the most part. But he also yielded an unthinkable 22 homers in 95 2/3 innings. Some speculated that pitching coach Mel Stottlemyre needed only work with Contreras to make him stop tipping his pitches.

Whatever the problem, the Yankees instead chose to cut bait, shipping Contreras to Chicago for Estéban Loaiza. After eight big-league seasons in which his lowest ERA was 4.13, Loaiza suddenly and mysteriously destroyed the AL in 2003, posting a 2.90 mark, winning 21 games and finishing second in the Cy Young voting. That the White Sox so willingly gave up on Loaiza just four months into the following season should have raised someone's radar. But the Yankees were so eager to rid themselves of Contreras that they overlooked Loaiza's spotty resume. Since then, Contreras has become the ace of the White Sox staff, his performance playing a huge role in Chicago's World Series win last season. Loaiza, meanwhile, has fallen back to Earth, countering his misleading 3.77 ERA in a pitcher's park in Washington with a horrendous performance in Oakland this year. He's got two years and $14 million worth of misery left to inflict on his employers, too.

Jonah Keri is a writer for's Page 2 and a contributor to He's also the editor and co-author of the book "Baseball Between the Numbers". You can reach him at comments