Most Terrible New York Yankees Trades

Synopsis: It was a dark and stormy night, perhaps somewhere in the world; however, in my environs the unblocked sunlight radiated from our nearest star and penetrated through the depleted ozone layer of the Earth’s atmospheric shell (for it is on this planet that our scene lies) before gently reflecting off the ecru walls surrounding my cubicle and onto a computer screen which hadn’t been cleaned for several months. Hopefully, you recognize my desire to pay homage to one of the best known examples of superbly horrendous writing. Regardless, I’d like to introduce you to a work of art so bad that it can only be called a masterpiece. Fashioned as a countdown of the most terrible New York Yankees trades, the piece reads more like the most terrible countdown of NYY trades instead.


Sometimes, extremes go so far that they flip around to the other side. For instance, you probably have seen animals so ugly that they actually look cute.

All together now. “Awww!”

Or, you’ve seen movies so bad that they become entertaining.

The best work done by Eye-an Ziering since Chippendales ever.

I can’t say that it happens frequently, but writing can be bad enough to become quite enjoyable. As support, I submit’s 15 of the Most Terrible New York Yankees Trades Ever. I have included the opening paragraph from the link as a teaser.


What the Yankees want the Yankees get. But during games, the Yankees haven’t always been in the right in terms of decision making. Having a lot of money in their pockets has allowed them to make quite a number of bad agent signings that are free and their scouts that are below average led them into making bad trades.

Well, do you agree? Apparently, the author believes “free-agent signings” are the same as “agent signings that are free.” To her credit, I assume “free agent” wasn’t properly hyphenated in the source document. Despite the surprisingly bad writing, something compelled me to click on the “Next Page” button.

Don’t worry, the article only gets worse better from there. As I read each subsequent paragraph, the writing got worse, yet more enjoyable. In fact, it amused me so much that I didn’t mind the extremely slow server. 

By no means do I intend to expose the author as a bad writer because she may not be one. As a quick background, she seems to be’s “How You . . ” girl. Specifically, she writes articles with titles such as “How You Can Prevent Razor Burn” or “How You Know You Should Go To The Eye Doctor.” In essence, she’s similar to Kate Hudson’s character in How to Lose a Guy in 10 Days (2003).

And, not because of the dress!

Working as a writer for Composure magazine in the movie, Andie Anderson (Hudson) gets labeled as the “How to . . ” girl. Of note, Anderson feels conflicted when forced by her editor (played wonderfully by Lilith Sternin Crane from Cheers) to write stories that don’t interest her. Similarly, I imagine that an editor at Today’s Lifestyle forced the site’s young “How You . . ” girl to write a sports story despite the writer’s protests.

Based on the final work product, it’s clear the writer doesn’t have the first clue about baseball. Arguably, she doesn’t have a clue about proofreading either. I’m sure my posts aren’t perfect, but there can be no comparison to the frequency and severity of the mistakes in her piece.

After reading one of the author’s other articles, I can accept that she may be a competent writer. Then again, her countdown of terrible New York Yankees trades could be best described as a terrible countdown of Yankees trades. Like what I did there?

At first I asked myself, “Is it possible that the author simply typed up her notes and someone accidentally published a very rough version of the final copy?” Upon further reflection, I just can’t give her a pass as if she turned in a rough draft. No joke, a 6th grader could do better. 

So then I asked myself, “Is it possible that the author wrote something so bad in order to dissuade her editor from ever giving her a sports story again?” Possible? . . .  Sure. Probable?  . . .  After re-reading her work, I say, “Absolutely!”


With respect to the countdown of the 15 Most Terrible New York Yankees Trades Ever, I’m convinced that the author didn’t do any independent research. Instead, I believe her editor gave her the specific trades and some notes about them. As confirmed by a ranking done by Bleacher Report, the selection of the trades seems remarkably similar. If you care to learn something useful about the trades, I recommend that you click the link to Bleacher Report . On the other hand, if you want to be entertained, click the link to Today’s Lifestyle instead.

As a third option, you can read the following summaries. Please note that the description of each trade comes directly from Today’s Lifestyle website. Furthermore, I have included the best lines from the article under the heading “Favorite Analysis.

#15 MOST TERRIBLE TRADE: “Trading Tyler Clippard meant for Jonathan Albaladejo”

Date: December 4, 2007.

Bleacher Report Rank: Not ranked.

Favorite Analysis: “At the moment Jonathan has not even pitched a big league ever since 2012 while on the other side Clippard continues to make impact in succession at the MLB.”

Commentary: If that sentence didn’t confuse you enough, how about this one? “Not only that, Clippard has been at the All-star game twice and a niche as the last minute reliever.”

#14 MOST TERRIBLE TRADE: “Trading bob Tewksbury for Steve Trout”

Date: July 13, 1987.

Bleacher Report Rank: Not ranked.

Favorite Analysis: “Trout’s performance was not at its appealing in the season with the Yankees as he went 0 – 4 with a six point six ERA in 9 starts and 5 relief appearance. ”

Commentary: While the analysis of the first trade confused me, this one served as the hook that made we want to keep reading. In particular, it’s spectacularly horrendous.

#13 MOST TERRIBLE TRADE: “Acquiring Kevin Brown”

Date: December 12, 2003.

Bleacher Report Rank: #8

Favorite Analysis: “Kevin Brown, a starting pitcher was regularly a CY youngest award candidate.”

Commentary: Hopefully, you caught the comment about the “CY youngest award.” Unfortunately, the author missed an opportunity to reveal that the Yankees sent future Cleveland Browns bust Brandon Weeden to the Dodgers as part of the trade.

#12 MOST TERRIBLE TRADE: “The trade of Mark Melancon and Jimmy Paredes for Lance Berkman”

Date: July 31, 2010.

Bleacher Report Rank: Not ranked.

Favorite Analysis: “Considering the timing of the trade, nobody could imagine that it was a major error for the Yankees but Mark Melancon as one the top baseball closers, it appeared worse.”

Commentary: Melacon led the MLB in 2015 with 51 saves. Interestingly, he can be considered the marquis player in three lopsided trades.

#11 MOST TERRIBLE TRADE: “Acquiring Jeff Weaver”

Date: July 5, 2002.

Bleacher Report Rank: #7

Favorite Analysis: “For return they acquired weaver who at that moment was 6 to 8 with a three point one eight ERA along with three shootouts for the tigers.”

Commentary: As a nice touch, the author referred to Ted Lilly as Lilly ted. Furthermore, she apparently created the concept of a “shootout” (versus a shutout). Regardless, Weaver had three shutouts in 17 starts before getting traded that season.

#10 MOST TERRIBLE TRADE: “Trading Armando Benitez for Jeff Nelson”

Date: August 6, 2003.

Bleacher Report Rank: #10

Favorite Analysis: “With nine games played with a one point nine three ERA to boast about, the Yankees had him traded to the Seattle Mariners for Jeff who struggled with the Yankees leaving many fans wondering about the move from Benitez when his pitching skills were impressing.”

Commentary: Have you ever heard of “impressing” pitching skills. Also, you gotta love someone who writes out a pitcher’s ERA (e.g. one point nine three vs 1.93).

#9 MOST TERRIBLE TRADE: “Trading Larry Gura for Fran Healy”

Date: May 16, 1976.

Bleacher Report Rank: Not ranked.

Favorite Analysis: “Less familiar names, Larry Gura and Fran Healy were too involved in a trade between the Kansas City royal and Yankees in the early 1976. The strange thing is Healy was only but a part time player of 0.125 for the Royals.”

Commentary: For me, the strangest thing involved understanding what a “player of 0.125” meant. FYI, Healy batted 0.125 in eight games during the 1976 season before getting traded.

#8 MOST TERRIBLE TRADE: “Trading Jose Contreras for Esteban Loaiza”

Date: July 31, 2004.

Bleacher Report Rank: #4

Favorite Analysis: “Though he was not a good starting pitcher, coming off a 2003 season where Esteban Loaiza scooped 21 games for the Chicago White Sox.”

Commentary: While technically only a sentence fragment, the quote provides a wonderful image of a pitcher “scooping” games. Apparently, pitching and scooping must be synonyms.

#7 MOST TERRIBLE TRADE: “Trading tommy Holmes”

Date: December 9, 1941.

Bleacher Report Rank: Not ranked.

Favorite Analysis: “There he [Holmes] didn’t have an opportunity to play even one game as he was traded to the MLB. He had an impressive season in the year 1942 and 1947 with 191.”

Commentary: How did the author even find out about this trade? Even ESPN’s Tim Kurkjian would be stumped if asked about it. Then again, the trade occurred two days after the attack on Pearl Harbor so I’m sure no one knew about it back then either. FYI, Holmes had 191 hits in 1947.

#6 MOST TERRIBLE TRADE: “Trading Javier Vazquez twice”

Dates: December 16, 2003 / January 11, 2005 / December 22, 2009.

Bleacher Report Rank: #3

Favorite Analysis: “1st trade with Montreal Expos costed the Yankees Nick Johnson and Juan Rivera. The Yankees then used him to acquire Randy the following year from Arizona at least to make something out of him. They later on surrendered Mealy Cabrera for Javier again.”

Commentary: The use of “costed” in place of “cost” and the omission of Randy Johnson’s last name seem too obvious. The author did win me over, however, by changing Melky Cabrera’s name to “Mealy.”

#5 MOST TERRIBLE TRADE: “Trading for Vernon wells with his big salary”

Date: March 26, 2013.

Bleacher Report Rank: Not ranked.

Favorite Analysis: “The Yankees acquired the star even though he still had $42 million still on his contract in the remaining two seasons. The player spent only one year at the Yankees slashing .233, .282, and .349 with a total of 11 runs.”

Commentary: As a minor correction, the Yankees only had to pick up $13 MM of Wells’ remaining $42 MM contract. Also, notice the repeated use of “still.”

#4 MOST TERRIBLE TRADE: “Trading Mike Lowell away”

Date: February 1, 1999.

Bleacher Report Rank: #6

Favorite Analysis: “The trade didn’t see the Yankees get anything good in return while on the other hand Mike went on having a very clean sheet record in his new club.”

Commentary: I can’t even begin to imagine what a “very clean sheet record” means. Perhaps Lowell never failed a PED test.

#3 MOST TERRIBLE TRADE: “Trading Willie McGee for Bob Sykes”

Date: October 21, 1981

Bleacher Report Rank: #2

Favorite Analysis: “Bob never played a game for his previous club being no good at the Yankees. On the other hand,  Willie went on having an 18 year career that included 2254 hits, .295 balling average and 352 stolen bases.”

Commentary: If “balling” average truly existed, I wonder if .295 would be “impressing” or not.

#2 MOST TERRIBLE TRADE: “Trading Jay Buhner for Ken Phelps”

Date: July 21, 1988.

Bleacher Report Rank: #5

Favorite Analysis: “Jay Buhner was yet another player with over 300 career home runs that included 3 straight seasons of over forty, that the Yankees traded off early. Ken only managed .240 with the Yankees in two seasons and was later on traded for a minor league.”

Commentary: The writing may not be good, but the analysis surprisingly is spot-on.

#1 MOST TERRIBLE TRADE: “Trading Fred McGriff”

Date: December 9, 1982.

Bleacher Report Rank: #1

Favorite Analysis: “New York traded Fred alongside other players to Toronto Blue Jay in the year 1982 for Dodd Tom and Dale Murray . . . He was traded with Mattingly whom the Yankees have never won a world series with.”

Commentary: Tom Dodd or Dodd Tom? Eh, whatever. I’m confused how McGriff could have been traded with (or for) a career Yankee. Actually, the whole sentence about Donnie Baseball makes no sense.


Of note, the only “terrible trade” ranked by Bleacher Report but missed by Today’s Lifestyle highlighted the trade of Scott Wiggins to the Blue Jays for Raul Mondesi on July 1, 2002. Even though Modesi didn’t produce with the Yankees, I agree with Today’s Lifestyle because Wiggins didn’t produce for Toronto either.

At this point, it’s below my pay grade to opine on the most terrible New York Yankees trades ever. I hope you appreciate the sarcasm because I haven’t earned a penny from this site. Then again, I would be remiss not to share at least a few thoughts about the actual trades. In particular, I’ll focus on the three worst trades from my point of view.


Apparently, both Bleacher Report and Today’s Lifestyle view the trade involving Fred McGriff as the worst one in Yankees history. To start, the trade involved a potential Hall of Famer for two short-timers. After getting traded by the Bronx Bombers, McGriff exploded for 493 home runs and 1,550 RBIs. Meanwhile Dale Murray had a 3-6 record and Tom Dodd had 1 home run and 2 RBIs while playing for the Yankees. The trade may seem “criminal,” but it’s not quite as bad as it seems. Of note, the Yankees traded McGriff as a 19-year-old more than three years away from his major league debut. As such, I couldn’t rank it ahead of the other two.

More importantly, I’d like to digress by saying that McGriff deserves to be in the Hall of Fame. Granted, his totals seem less impressive because he played during MLB’s steroid era. However, the following pictures show that “Crime Dog” passes the eye test for being clean. Said differently, he had a “clean sheet record.”

McGriff prior to any career HRs


McGriff after 480 career HRs

When your career stats compare most closely to Willie McCovey and Willie Stargell’s, you certainly deserve a spot in Cooperstown.

#2 MOST TERRIBLE YANKEES TRADE: Willie McGee for Bob Sykes

Speaking of Willies, the trade of Willie McGee for Bob Sykes ranks as #2 on my countdown of terrible New York Yankees trades. Although not worthy of the Hall of Fame, McGee won an MVP award. He also served as one of the game’s best leadoff hitters throughout the 80s.

As part of the other half of the trade, pitcher Bob Sykes offered absolutely no value. Specifically, he never “scooped” a game for the Yankees, or any other team after the trade.

#1 MOST TERRIBLE YANKEES TRADE: Jay Buhner for Ken Phelps

For me, the Yankees’ all-time worst trade involved Ken Phelps and Jay Buhner. Specifically, the Yankees gave up Jay Buhner, Rick Balabon and Troy Evers to the Seattle Mariners for Ken Phelps. I could provide a legitimate argument, but why bother when Jerry Costanza can do it for me.

Terrible New York Yankees Trades - Buhner for Phelps
Click here for Jerry Costanza’s take on one of the Most Terrible New York Yankees Trades

Whenever a sports story extends into pop culture, it clearly deserves special consideration. In this case, it’s worthy of earning the #1 spot.

I understand that saying something’s funny doesn’t make it so. However, I hope you appreciated my effort in the spirit of Mystery Science Theater 3000. If I failed, I apologize because the article truly provides entertainment in a unique way. Then again, it took me two viewings to appreciate the humor of This is Spinal Tap (1984) so perhaps it’ll take some time before this post goes to 11.

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