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The 10 Worst Trades In Cubs History

This list will live in infamy.

Would Lou Brock have had his Hall of Fame career as a Cub?
Would Lou Brock have had his Hall of Fame career as a Cub?
Getty Images

Last week, Josh wrote this article chronicling his choices for the 10 greatest trades in Cubs history.

I asked him if he wanted to write the companion piece about the 10 worst deals. He said it would be too depressing.

Still, I thought it would be worth looking at this not-so-great part of Cubs history. There's absolutely no suspense involved here, as everyone knows what swap will occupy the No. 1 spot on this list. Others you might have (rightfully) forgotten about.

One note before we begin: You'll notice that all of these trades were made after World War II, following the Cubs' last pennant. The reasons for that should be fairly obvious; first, the Cubs were generally a well-run franchise pre-WWII and so the trades they made in that era were usually successful. Also, as Josh noted in his article, sending players from team to team back then often was a cash deal, rather than involving players being traded for each other.

Thus, as a reminder of how bad some previous Cubs regimes were about trading, here are my choices for the 10 worst trades in Cubs history.

10. July 29, 1998: The Cubs acquire Matt Karchner from the White Sox for Jon Garland

This one made little sense from any standpoint. Sure, the Cubs needed a righthanded setup man for Rod Beck, but Karchner had pitched poorly for the White Sox (5.15 ERA, 1.418 WHIP in 32 games covering 36⅔ innings) despite posting 11 saves. He wasn't any better for the Cubs (5.14 ERA, 1.571 WHIP). Garland had been drafted No. 1 by the Cubs just a little over one year earlier and wound up having a decent, if unspectacular, career (22.2 WAR in 13 seasons). He'd have looked real good in the Cubs' 2003 rotation.

9. November 21, 1972: The Cubs acquire Bob Locker from the Athletics for Bill North

The Cubs had been at the forefront of signing black players in the 1950s and developed several stars, including Hall of Famers Billy Williams and Ernie Banks. But when baseball and American culture began to change in the 1960s and 1970s, Cubs management was far behind the times. Management didn't understand black players like North, nor were they willing to use a player with stolen-base skills like his in the way baseball was adapting. Locker had a decent 1973 season, but North stole 232 bases in his six years in Oakland, leading the American League twice and was a key player on the A's playoff teams from 1973-75.

8. November 17, 1969: The Cubs acquire Johnny Callison from the Phillies for Oscar Gamble and Dick Selma

Again, racism might have been the catalyst for this deal. There was talk that Gamble was dating a white woman, something backwards Cubs management wouldn't abide. Gamble, just 19, had played well enough in Double-A to get a promotion to the big-league club in September 1969, when they were desperate for anything to jumpstart a moribund offense. Callison had been a pretty good power hitter from 1962-65, but five years later he was in serious decline. Gamble went on to hit 200 major-league homers, while Callison had a mediocre 1970, a worse 1971, and then was shipped to the Yankees for reliever Jack Aker.

7. December 8, 1987: The Cubs acquire Calvin Schiraldi and Al Nipper from the Red Sox for Lee Smith

Smith had a horrendous 1987 season after several years as a solid closer. Despite saving 36 games, he had 12 blown saves and was being booed routinely. Jim Frey, who was out of his league as newly-named general manager, caved to fan pressure (something that would never happen today) and swapped Smith. Unfortunately, he made the wrong deal. Supposedly, the Dodgers had offered Bob Welch straight-up for Smith; that would have been a far better trade than was made. Another rumored offer was from the Braves: Jeff Blauser (when he was still good) and a kid pitcher named John Smoltz for Smith.

Instead, Frey took Nipper and Schiraldi. Schiraldi was psychologically damaged from having helped Boston blow Game 6 of the 1986 World Series and was described to me by one person who saw him in the Cubs' clubhouse as "flabby." Nipper was a nonentity who was released after one poor season with the Cubs.

Smith went on to save 298 more games; his total of 487 ranks third all-time and he's still a Hall of Fame candidate.

6. December 5, 1988: The Cubs acquire Mitch Williams, Curtis Wilkerson, Paul Kilgus, Steve Wilson and Pablo Delgado from the Rangers for Jamie Moyer, Rafael Palmeiro and Drew Hall

An eight-player swap! You don't see many of those any more.

The Cubs had a choice after 1988. Mark Grace and Palmeiro were both first basemen. Palmeiro had played in left field, but he was ill-suited there (and played just one game there after he left the Cubs). They could have traded either one, but chose Palmeiro.

Granted, the Cubs got help winning the 1989 N.L. East title from Williams, though they might not have had to make this deal if they'd have kept Smith. Palmeiro, who never showed power in the Cubs system nor in his two-plus years on the big-league squad, went on to hit over 500 home runs (with a PED asterisk) and Moyer pitched for more than 20 more seasons. The Cubs could have had Moyer back; they invited him to spring training in 1992 after he'd been released by the Cardinals. He didn't make the 1992 major-league squad (and he'd surely have been better than Shawn Boskie) and was offered a spot in the organization as a minor-league coach. He turned it down and told Cubs management he thought he could still pitch.

5. June 15, 1951: The Cubs acquire Bruce Edwards, Joe Hatten, Gene Hermanski and Eddie Miksis from the Dodgers for Andy Pafko, Johnny Schmitz, Wayne Terwilliger and Rube Walker

This was a panic move. Somehow, the Cubs thought they could contend in 1951 and had, in fact, been in or around first place much of April and May. In late May and early June they lost 14 of 19 and general manager Jim Gallagher decided to do something, anything, to change things.

Pafko had been a four-time All-Star and had his best season in 1950. He was a popular player and loved Chicago. Here's what I wrote about this deal two years ago; it was done for no other reason, as manager Frank Frisch was quoted, because "We had to do something."

It was the wrong "something." Pafko went on to play in three World Series with the Dodgers and Braves, though he never had the sort of production he had in Wrigley Field. None of the players the Cubs acquired ever did anything significant in Chicago and only Miksis lasted with the team past 1954.

4. December 11, 1956: The Cubs acquire Ray Katt, Tom Poholsky, Jackie Collum and Wally Lammers from the Cardinals for Sam Jones, Hobie Landrith, Eddie Miksis and Jim Davis

Jones had thrown a no-hitter for the Cubs in 1955 and had a decent year in 1956. The Cubs needed pitching. This trade is inexplicable, and Jones went on to the Giants and had a spectacular 1959 season (21-15, a league-leading 2.83 ERA and four shutouts). If there had been separate league Cy Young Awards in 1959 (there was just one until 1967) he surely would have won the N.L. award.

Of the four players acquired, Lammers never played in the major leagues, Katt was traded to the Giants before ever playing a game for the Cubs, Poholsky pitched poorly in 1957 and was traded (also to the Giants) and Collum pitched in only nine games for the Cubs before being traded to the Dodgers for Don Elston, who provided the only real value the Cubs ever got from the Jones deal.

The 1959 National League was what Bill James once termed a "compressed league" -- a league or division where all the teams are very close together. From first to seventh that year, the spread was just 16 games. Jones posted 5.7 bWAR in 1959, fourth-best among pitchers. The Cubs had the league's worst pitching by bWAR, -5.9. It's not a stretch to say that if they'd had Jones in 1959, a year when Ernie Banks won his second MVP, replacing others who pitched poorly or were injured, they might have had a contending team.

3. February 11, 1977: The Cubs acquire Bobby Murcer, Steve Ontiveros and Andrew Muhlstock from the Giants for Bill Madlock and Rob Sperring

Latent racism rears its ugly head again. After winning the N.L. batting title in 1975 and 1976, Madlock had made contract demands that mangement didn't like. That's fine on the surface, but the Cubs wound up giving Murcer more money than Madlock had asked for, raising the question of whether money or something else prompted this deal. They also got an older player who never really wanted to be a Cub, never seemed comfortable in Chicago and whose power nearly completely vanished after he'd started off the 1977 season pretty well.

Madlock's .336 average in 1,481 at-bats as a Cub is the highest in the history of the franchise for anyone who had that many at-bats with the team. Though he went on to have a good career with five other teams and won two more batting titles, it's possible he could have had a better career if he'd stayed in Chicago.

2. April 3, 1987: The Cubs acquire Brian Guinn, Mark Leonette and David Wilder from the Athletics for Dennis Eckersley

None of the players the Cubs acquired in this deal ever played in the major leagues.

It's hard to say whether Eckersley would have had his eventual Hall-of-Fame performance had he played for any manager other than Tony La Russa, who was willing to convert the former starter into the first modern closer. The Cubs could have done that, and that would have made the trade of Lee Smith later that year more palatable. For whatever reason, they weren't willing to do so, and so this one has to go down as not only short-sighted, but poorly executed in that the Cubs got no one of value.

You might recognize Wilder's name. He started a front-office career in the early 1990s and by 1996 was director of minor-league operations for the Cubs, eventually becoming assistant general manger. He eventually moved to executive positions with the Brewers and White Sox; it was with the latter as director of player development that he became involved in skimming parts of bonus payments made to some Latin American players. Wilder was eventually convicted of mail fraud and is currently serving a two-year prison term.

1. June 15, 1964: The Cubs acquire Ernie Broglio, Doug Clemens and Bobby Shantz from the Cardinals for Lou Brock, Jack Spring and Paul Toth

Not only is this the worst trade in the history of the Cubs, it's got a claim to be the worst trade in baseball history.

True, at the time it was made baseball writers praised the Cubs, as Broglio had had a fine 1963 season (18-8, 2.99 ERA, 1.168 WHIP, 3.4 bWAR) and was just 27. Brock appeared to be a failure.

The trouble was, Cubs management either didn't recognize or refused to make use of Brock's obvious talent in basestealing. 10 years later, with Bill North, they still wouldn't join the speed game that was revolutionizing baseball. The coaching staff instead spent time trying to turn Brock into a power hitter like his teammates Billy Williams and George Altman (he'd become one of only two players to hit a home run into the center-field bleachers in the Polo Grounds in 1962), but he didn't really make use of his speed till he got to St. Louis. There, management immediately let him run to his heart's content. Would he have done the same had he stayed in Chicago? Doubtful, as the 24 bases Brock stole for the Cubs in 1963 represents the highest single-season total for any Cub between 1930 (Kiki Cuyler, 37) and 1966, when Adolfo Phillips, another player mishandled by Cubs management, swiped 32.

Dishonorable mention to the following deals:

  • December 6, 1959: Bill Henry, Lou Jackson and Lee Walls traded to the Reds for "the other" Frank Thomas
  • May 13, 1960: Tony Taylor and Cal Neeman traded to the Phillies for Ed Bouchee and Don Cardwell
  • May 28, 1966: Ted Abernathy traded to the Braves for Lee Thomas
  • November 30, 1967: Ray Culp traded to the Red Sox for Bill Schlesinger
  • August 31, 1973: Larry Gura traded to the Rangers for Mike Paul
  • June 10, 1978: Ron Davis traded to the Yankees for Ken Holtzman
  • May 22, 1983: Willie Hernandez traded to the Phillies for Dick Ruthven and Bill Johnson
  • May 21, 1999: Kyle Lohse and Jason Ryan traded to the Twins for Rick Aguilera