The Most Lopsided Trade of All-Time!

The Most Lopsided Trade of All-Time!


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Most Lopsided Trade of All Time!

Awhile back I started a series on lopsided trades. Some of you may remember a couple of the more notorious ones I featured: the Lou Brock for Ernie Broglio trade that causes heart-burn to Cub fans even to this day; and the Frank Robinson for Milt Pappas fiasco from which many Reds fans are likewise are still hurting.

But today, I think I’ve discovered the most lopsided trade in the history of baseball. Granted, it happened a long time ago, but it still counts. What if I told you there was once a 4-player-for-14-player swap which sent three future Hall-of-Famers one way for four unknowns? Would you believe me? Yes, it happened in 1899 in a trade between the Pittsburgh Pirates and the Louisville Colonials. It actually makes Brock-for Broglio look mild by comparison!

Here’s what the Pirates got in this one-sided deal: Honus Wagner, possibly the greatest shortstop and all-around player ever; Hall-of Fame pitcher Rube Waddell; Hall-of-Fame outfielder and future manager Fred Clarke; future ace pitcher Deacon Phillippe who in 12 years with the Pirates went 168-92 (.646); plus star infielders Claude Richey and Tommy Leach; and steady catcher Chief Zimmer. Not a bad haul for the Pirates!

In the featured photo above, we see a beautiful photo of Honus Wagner, the centerpiece of this trade, colorized by our friend, Don Stokes. 

This trade turned a good Pirates team into a powerhouse which won pennants in 1901, ‘02 and ’03, and appeared in the first World Series in 1903. The 1902 Pirates were one of the greatest teams of all-time.  They outscored the next-best team by 142 runs and led the National League in hits, doubles, triples, batting average, on-base percentage, slugging average, and tied for the league lead in stolen bases. Their 103-36 record put them an amazing 27 ½ games ahead of second place Brooklyn, and their .741 winning percentage is the second highest in the 20th century. Over a 162 game schedule that computes to a 120-42 record. The 1902 Pirate offense was built around Ginger Beaumont, who led the league with a .357 average; plus the additions of Wagner (.330);  Clarke (.326); and third baseman Leach whose 22 triples and six homers led all National League batters, finishing second to Wagner in RBIs. Wagner led the league in runs, doubles, RBI, and slugging average.

Newcomer Deacon Phillippe won 20 games that year and was a welcome addition to a staff that already included Jack Chesbro (28-6), Jesse Tannehill (20-6), Ed Doheny (16-4), and Sam Leever (15-7).

This trade was actually orchestrated by Louisville owner Barney Dreyfuss…and it worked out pretty good for him, too. The Pirates paid him $25,000 to settle Louisville debts. In addition, they gave him a half-interest in the Pittsburgh franchise!

And who did the Pirates give up in this one-sided deal? Well, I can guarantee you they’re names you’ve never hear of (except perhaps for Jack Chesboro who later returned to the Pirates). All-in-all, I’d say this deal worked out pretty good for the Bucs. They were contenders for the rest of the decade and won another pennant and their first World Series championship in 1909.

-Gary Livacari

Photo Credits: Colorization by Don Stokes:; other from public domain

Information: Edited from “The Best of Baseball,” by Paul Adomites

Subscribe to my blog for automatic updates and Free Bonus Reports: “Memorable World Series Moments” and “Gary’s Handy Dandy World Series Reference Guide.”


I'm a baseball historian who also loves to write. My forte is identifying ballplayers in old photos, and my specail interest is the Dead Ball Era.

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