Evaluating a baseball trade -- particularly identifying winners and losers -- is never a straightforward process.
First, most trades are made by teams in different situations. One might be aimed more at the future, while the other is trying to get over the hump right now. Or one team might be trying to navigate a cluttered payroll, while the other has cleared its books and is ready and willing to take on money. Judging trades is tough when they happen, and even with the benefit of hindsight, it's often not merely a matter of saying, These players produced more WAR than these other players.
That said, trades that turn out to be objectively one-sided have provided some of the more colorful liner notes in baseball history. Once upon a time, a bad deal might have been struck in some hotel lobby, where one back-slapping owner might have shaken hands with a compatriot during the wee hours of the morning.
That kind of swapping is now more myth than reality. Modern teams have numbers-crunchers and grizzled scouts behind every deal they strike and sophisticated models for assigning valuations. Still, bad trades happen. Dealmaking remains an inexact science, often driven by intangible forces for which no trade valuation model can account.
The irony is that every bad baseball deal ever struck made sense to the team drawing the short end of the stick at the time the trade was made. What's more: In most cases, you can argue that the reasoning for that bad trade was sound, when considered in context.
And so we reach our theme for today: What was the reasoning behind some of baseball's most infamous trades?
Perhaps more importantly: Are there lessons from these deals that teams need to take to heart with the 2021 trade deadline approaching?
What is a bad trade? For our purposes at the moment, let's define it as any deal that in hindsight looks so one-sided that the perception lingers that it didn't make sense in the first place.
That definition is subjective, but there is general consensus about what the worst trades in baseball's annals have been. If you Google the term "baseball's worst trades" you get numerous matches, but the deals identified in those articles tend to show up again and again. That suggests that if certain trades weren't actually that bad, they were at least perceived to be so.
To narrow things down, we began by creating a long list of "bad" trades from books written on the subject, books about baseball executives and all of those articles Google discovered. If you have written such an article, chances are one of your bad trades ended up on the initial list.
Eventually, after identifying deals that showed up multiple times in these various sources, we came up with a list of 100 bad trades. We then attempted to classify these trades, using general descriptive terms.
From each classification of bad trade, we picked one to examine for its in-the-moment reasoning. In other words, we're going to make the case for the side that made the bad deal. And since we know these trades didn't turn out well, we will try to summarize what the cautionary tale reveals.
The premature white flag
1997: Chicago White Sox trade Wilson Alvarez, Danny Darwin and Roberto Hernandez to the San Francisco Giants for Brian Manning, Lorenzo Barcelo, Mike Caruso, Keith Foulke, Bob Howry and Ken Vining
Contemporaneous quote: "Anyone who thinks this White Sox team will catch Cleveland is crazy." -- White Sox owner Jerry Reinsdorf (via Chicago Sun-Times)
Rationalizing the indefensible: "Look, we're stuck in the middle. We won a couple of games lately, but we're still only .500 and we've been outscored by 11 runs. We're only 3½ games behind Cleveland, but compare the rosters. We're just not good enough. We got here with Hernandez, Darwin and Alvarez, and who's to say these young guys can't do better? Besides, those guys are all free agents after the season. Chances are, if we don't do this, we lose them for nothing."
Why it turned out bad: You could argue that it didn't. Hernandez helped the Giants get to the postseason, then struggled during an NLDS loss to Florida. Darwin stuck around for another year with the Giants, but that was it for him -- he was 40 years old. Alvarez and Hernandez both signed with the expansion Tampa Bay Devil Rays. Meanwhile, Howry and, later, Foulke both became effective closers for the White Sox.
The reason this deal makes so many bad trade lists traces back to Reinsdorf's comments -- which, by the way, he walked back the next day. Simply put: The trade was portrayed as the White Sox giving up on the season. Now teams often walk the line between managing short-term contention with long-term financial interests. The North Side Cubs are doing it right now.
Lesson learned: Don't say the quiet part out loud.
Other trades of this type:
1998: Seattle Mariners trade Randy Johnson to the Houston Astros for Freddy Garcia, Carlos Guillen and John Halama
2004: Oakland Athletics trade Tim Hudson to the Atlanta Braves for Juan Cruz, Dan Meyer and Charles Thomas (offseason white flag)
2018: Miami Marlins trade Christian Yelich to the Milwaukee Brewers for Lewis Brinson, Monte Harrison, Isan Diaz and Jordan Yamamoto (offseason white flag)
Blame it on the owner
2018: Pittsburgh Pirates trade Tyler Glasnow, Austin Meadows and player to be named later (Shane Baz) to the Tampa Bay Rays for Chris Archer
Contemporaneous quote: "If you told every GM that you could be guaranteed a World Series, every single one of us would mortgage the future. But there is no guarantee." -- Pirates general manage Neal Huntington (via Pittsburgh Post-Gazette)
Rationalizing the indefensible: "Look, you guys have been hammering us for years about not being aggressive enough during the season. You complained about us being too precious with our prospects. Chris Archer is a really good pitcher and is going to help us get back to the playoffs and has multiple years left on a reasonable contract. We're three games over .500 even though our rotation hasn't had a true No. 1. Now we have one. We love Glasnow and Meadows, but this is about seizing an opportunity. And look -- everyone loves us today. We won the trade deadline."
Why it turned out bad: First, the Pirates judged Archer for who they wanted him to be, not who he was. Archer was one of the AL's better starters from 2013 to 2015. And while he remained a viable rotation member after that, he had rolled up a lot of innings and had not been producing like anything close to an ace for some time. He led the AL in losses (19) in 2016 and had an ERA+ of just 95 during 2018 before the trade. During his time with the Pirates, that number was 86.
Second, the Pirates didn't properly value Meadows, who had already turned the corner from top prospect to productive big leaguer. And they whiffed at finishing off the development of Glasnow, who has always had the sort of power arm that makes teams googly-eyed. He almost immediately became a top-of-the-rotation performer in Tampa Bay.
The trade just keeps getting worse over time. Archer is back with the Rays (see photo with Glasnow above), though he hasn't contributed much this season. And the PTBNL in the deal -- Baz -- has become one of the more scintillating pitching prospects around. In 55⅔ innings this season across Double-A and Triple-A, Baz has a 2.26 ERA, 82 strikeouts and just 10 walks allowed.
Owner Robert Nutting's specific role in the deal is unclear. Did he mandate the trade? Probably not. But he did sign off on it, perhaps awed by Archer's team-friendly contract. And perhaps Huntington and his staff were willing to trade such a promising group of players at that moment because they had not been allowed to be aggressive in prior situations. And they heard about those situations, again and again and again, from a fan base that remains ripe with antipathy toward the owner.
Lesson learned: It's tempting to say you should not deal with the Rays, but a more general observation is you can't let fan and media pressure cloud your evaluation about both sides of a prospective trade.
Other trades of this type:
1919: Boston Red Sox trade Babe Ruth to the New York Yankees for $100,000
1988: New York Yankees trade Jay Buhner to the Seattle Mariners for Ken Phelps
1997: Los Angeles Dodgers trade Mike Piazza to the Miami Marlins for Gary Sheffield, Bobby Bonilla and Charles Johnson
This guy is a pain in the butt
1972: St. Louis Cardinals trade Steve Carlton to the Philadelphia Phillies for Rick Wise
Contemporaneous quote: "I guess, really, this thing was generated by our [salary] differences with Carlton two years ago. We could sense a similar situation developing." -- Cardinals GM Bing Devine (via The Associated Press)
Rationalizing the indefensible: "Look, Carlton has had his moments, but he led the league in losses just a couple of years ago. And every year, it's the same thing: More money. More money. In Wise, we get a pitcher almost as good and who will give us many fewer headaches. I mean, Wise is really good. He won 17 games last year for a Phillies team that lost 95."
Why it turned out bad: It really wasn't the fault of poor Rick Wise. He had a very good career, winning 188 games and earning a couple of All-Star berths. He was the same pitcher before the Carlton trade as he was after. The problem is that St. Louis didn't get more in the deal, if we are willing to grant that the Cardinals had to part ways with the combative Carlton.
It's hard to argue the "had to" part of that. Remember this was pre-free agency. The Cardinals simply did not have to trade Carlton. Carlton was always, shall we say, different. He's also permanently enshrined in Cooperstown. Wise won 17 games for a bad Phillies team, but Carlton won 27 for a really bad Phillies team. And he was still around winning Cy Youngs when the Phillies won the 1980 World Series.
You have to believe that at the bottom of it, this trade was less about Devine's faith in Wise than it was about St. Louis owner Augie Busch being exasperated by Carlton. It was a large price to pay for exasperation.
Lesson learned: If you have to deal away a star player who gets on your nerves, get a fair return in talent for him.
Other trades of this type:
1981: San Diego Padres trade Ozzie Smith and Steve Mura to the Cardinals for Garry Templeton and Sixto Lezcano
1983: St. Louis Cardinals trade Keith Hernandez to the New York Mets for pitchers Neil Allen and Rick Ownbey
1979: Minnesota Twins trade Rod Carew to the California Angels for Ken Landreaux, Dave Engle, Paul Hartzell and Brad Havens
Can't afford to keep The Franchise
1977: New York Mets trade Tom Seaver to the Cincinnati Reds for Pat Zachry, Doug Flynn, Steve Henderson and Dan Norman
Contemporaneous quote: "This has to be one of the biggest steals since the Babe Ruth trade. A trade is supposed to help both teams. But I don't think the Mets are as good a club as they were before. I can't see how they improved their team one iota." -- Dodgers infielder Davey Lopes (via New York Times)
Rationalizing the indefensible: "Look, we honor and thank Tom Seaver for all the great things he's done for the Mets franchise. But he's just too darned hard-headed. He's making good money, but always wants more. On top of that, he wants to run the team, too, telling us we need another hitter. Well, let me tell you: As good as Tom is, he's 32 years old. Pat Zachry is just 24 and he was one of the better rookies last season. He's going to win a lot of games for us. Plus, Flynn and Henderson are going to be regulars. I know fans are mad now, but check back with us in a couple of years."
Why it turned out bad: Zachry did in fact have a strong 1976 season, winning NL Rookie of the Year honors with a 14-7 record and 2.74 ERA over 204 innings for the champion Reds. That turned out to be his best season. Meanwhile, Seaver may indeed have been on the downside, but he was still really good and enjoyed four-plus good seasons for Cincinnati before returning to the Mets in 1983 for an encore season.
The sad thing is that this kind of trade has become more or less commonplace, and it hurts fan bases. Seaver was the greatest player in the history of the Mets and may still hold that title. He set the template for a franchise that has always been driven by starting pitching. And he was still going strong for a Mets team that was not trying to rebuild but reload.
Lesson learned: Don't betray your own fans.
Other trades of this type:
1997: Oakland Athletics trade Mark McGwire to the St. Louis Cardinals for T.J. Mathews, Eric Ludwick and Blake Stein
2007: Florida Marlins trade Miguel Cabrera and Dontrelle Willis to the Detroit Tigers for Cameron Maybin, Andrew Miller, Mike Rabelo, Burke Badenhop, Dallas Trahern and Frankie De La Cruz
2017: Miami Marlins trade Giancarlo Stanton and $30 million to the New York Yankees for Starlin Castro, Jorge Guzman and Jose Devers
Believe in the talent
1987: Chicago Cubs trade Dennis Eckersley and Dan Rohn to the Oakland Athletics for David Wilder, Brian Guinn and Mark Leonette
Contemporaneous quote: "Obviously, I'm going to say I want to start. But this is the best position for me to help the team." -- Dennis Eckersley, after being shifted to the closer role that made him famous (via The Sporting News)
Rationalizing the indefensible: "Look, Eckersley is washed up. I hate to put it that way, but look at the facts. He went 6-11 last season and his ERA was way over the National League average. He's 31 years old and has been hard on himself off the field. This guy used to be a fireballer, but he hasn't struck out 150 batters since Jimmy Carter's first year in the White House. The fact that we got three young players for him is a miracle."
Why it turned out bad: The return for the Cubs on the deal was abysmal. None of the three minor leaguers they dealt for made it to the majors. And we all know what happened to Eck: A solid career became a legendary one. Operating as Tony La Russa's one-inning closer, he helped redefine bullpen structures. That outcome was perhaps not Oakland's rationale for the deal, as Eckersley actually made two starts for the team before making the switch. But that was the outcome nonetheless.
Lesson learned: Unless you are knocked over by a trade offer, if you have a talented player struggling in some way, you'd better make sure you've turned over every stone looking for his comfort zone, or some other team is going to reap the benefits.
Other trades of this type:
1972: Boston Red Sox trade Sparky Lyle to the New York Yankees for Danny Cater
1996: Seattle Mariners trade David Ortiz to the Minnesota Twins for Dave Hollins
2013: Baltimore Orioles trade Jake Arrieta and Pedro Strop to the Chicago Cubs for Steve Clevenger and Scott Feldman
The missing piece
1990: Boston Red Sox trade Jeff Bagwell to the Houston Astros for Larry Andersen
Contemporaneous quote: "Larry is a veteran reliever who should bolster our bullpen for the stretch run. Although the price was high, we are happy to have acquired a pitcher with postseason experience." -- Red Sox GM Lou Gorman (via AP)
Rationalizing the indefensible: "Look, we're in this thing. We haven't won a World Series during the lifetime of most of our fans. This all about putting our best foot forward in October. Bagwell is a talented kid, but minor leaguers don't end World Series droughts. Anderson has been unhittable for two years now."
Why it turned out bad: This was a waiver-deadline deal, taking place on the last day of August 1990. At the time, the Red Sox had a 6½-game lead on the Blue Jays in the AL East. But they did have a sore spot in the bullpen, with a league-worst 4.75 bullpen ERA. Meanwhile, Andersen was in the midst of a two-year stretch in which he posted at 1.67 ERA over 183⅓ relief innings. He was also about to become a free agent.
On the other hand, Bagwell was a native New Englander taken in the fourth round of the 1989 draft. At the time he was traded, he was leading the Eastern League with a .333 average and plenty of extra-base hits that teased what was to come in the power category. He was starting for Houston in the big leagues the very next season.
Maybe it was the crush of history that made this trade happen. And Boston had one young first baseman as a regular already (Carlos Quintana) and another one on the way (Mo Vaughn). Still, the value of production you'd get from Andersen over one month and a couple of playoff games as compared to what you could get from Bagwell simply did not add up. No team would make this deal under those circumstances now, title drought or not.
Lesson learned: Recognize scarcity of certain classifications of talent. Yes, Andersen was a solid reliever for a long time. So, too, were many others. Meanwhile, Bagwell was already displaying his elite bat in the minor leagues. He was too good to be traded for a reliever.
Other trades of this type:
1975: Pittsburgh Pirates trade Willie Randolph, Dock Ellis and Ken Brett to the New York Yankees for Doc Medich
1987: Detroit Tigers trade John Smoltz to the Atlanta Braves for Doyle Alexander
2012: Texas Rangers trade Kyle Hendricks and Christian Villanueva to the Chicago Cubs for Ryan Dempster
We really need to fill that position
1993: Los Angeles Dodgers trade Pedro Martinez to the Montreal Expos for Delino DeShields
Contemporaneous quote: "We felt Delino would be more valuable to us than a relief pitcher." -- Dodgers GM Fred Claire (via San Bernardino Sun)
Rationalizing the indefensible: "Look, Jody Reed is a free agent and we need a second baseman. This is a chance to get younger and more athletic at the position. Think of what Tommy Lasorda can do with speedsters like DeShields and Brett Butler atop the lineup. DeShields gets on base and is a cinch for at least 40 steals a season. Pedro is a talented kid, but he's undersized and we rode him pretty hard last season. This is a no-brainer."
Why it turned out bad: Some of it was bad luck for the Dodgers. If DeShields had played better for them, then perhaps history would not judge them so harshly. Perhaps. But he ended up hitting .241 over three years in L.A. with little power.
And ... Pedro became Pedro, and not as a relief pitcher. The Dodgers used him as one when he was a 21-year-old rookie, and he went 10-5 over 107 innings and struck out 10 batters per nine innings, two more than any other L.A. pitcher who threw at least 30 innings. Montreal immediately put him in the rotation, and he became one of the most dominant and successful pitchers of all time.
Lesson learned: Value high-end talent for what it is. If you have a hole in a lineup or rotation or bullpen, settle for stopgaps if the only way you can fill it is to deal away an elite talent.
Other trades of this type:
1982: Philadelphia Phillies trade Ryne Sandberg and Larry Bowa to the Chicago Cubs for Ivan DeJesus
1991: Houston Astros trade Kenny Lofton to the Cleveland Indians for Eddie Taubensee
2016: Chicago White Sox trade Fernando Tatis Jr. and Eric Johnson to the San Diego Padres for James Shields
Better a year too early
1965: Cincinnati Reds trade Frank Robinson to the Baltimore Orioles for Milt Pappas, Jack Baldschun and Dick Simpson
Contemporaneous quote: "The Reds called him up and said he had been traded. He just asked them who he had been traded for. [Reds assistant GM Phil] Seghi told him and he said 'OK' and left." -- Barbara Ann Cole, Frank Robinson's wife, who explained to a reporter after the trade that Robinson had gone bowling (via AP)
Bonus contemporaneous quote: "According to my figures, Robinson is worth a half-million dollars. The three players we got also are worth a half-million. I think it was an even deal." -- Reds owner and general manager Bill DeWitt Sr. (via UPI)
Rationalizing the indefensible: "Look, Robbie has been great, but he's 10 years in the league by now. How many good years does he have left? We led the National League in runs last season by a mile. So, yeah, we may score a little less. But we'll be giving up a lot fewer runs and for many years to come. If we had better pitching last year, we'd have won the pennant. Pappas is really good. He was the best pitcher on a very good team, leading Baltimore in innings and complete games. And he's only 26. His best is yet to come."
Why it turned out bad: After he finished bowling, Robinson went to Baltimore and won the AL Triple Crown in 1966, leading the Orioles to a World Series title and winning his second MVP award. He hit .316/.410/.637 with 49 homers, 122 RBIs and 122 runs scored. Then there is this: Robinson played 21 years in the majors, so 1966 was his "middle" season. During the 10 seasons before that, he posted a 150 OPS+. During the 10 seasons after that, he posted a 154 OPS+, albeit in less playing time.
As for Pappas, he was OK, just as he had always been. He ended up winning 209 games in the bigs and had every reason to be proud of his career. But he was no Frank Robinson.
Lesson learned: A lot of teams now follow Branch Rickey's old dictum about trading a player a year too early rather than a year too late. The thing is, the Reds traded Robinson several years too early. Don't do that with an all-time talent.
Other trades of this type:
1976: Cincinnati Reds trade Tony Perez and Will McEnaney to the Montreal Expos for Woodie Fryman and Dale Murray
1996: Boston Red Sox trade Jamie Moyer to the Seattle Mariners for Darren Bragg
2000: Los Angeles Angels trade Jim Edmonds to the St. Louis Cardinals for Adam Kennedy and Kent Bottenfield
It's time to rebuild
1993: San Diego Padres trade Fred McGriff to the Atlanta Braves for Melvin Nieves, Donnie Elliott and Vince Moore
Contemporaneous quote: "We didn't get any of the guys that were talked about. At least, those guys I had heard of, or seen on TV, playing for the Braves. These other guys -- I don't have a clue. I really don't. It's not my job to make those deals, but from a player's perspective, it's surprising we didn't get any of those guys." -- Padres' future Hall of Famer Tony Gwynn (via San Diego Union-Tribune)
Rationalizing the indefensible: "Look, we're terrible. We'll probably lose 100 games. McGriff has been great for us, but we need to get younger and the Braves' system is rich in young talent."
Why it turned out bad: The Padres were indeed having a bad 1993 season. This trade could have easily been classified as an owner-mandated deal, as San Diego's moves at the time were portrayed as a fire sale. Still, McGriff was under contract for two more years after that season. Nieves was a fairly strong prospect who never panned out, but if the Padres were looking to pivot, they had to get more for an in-his-prime player like Crime Dog. McGriff hit another 284 big-league homers after leaving San Diego.
Lesson learned: If you're going to be cheap, at least get a reasonable return when you're talking about an All-Star with multiple years of control left on a contract, even if you have to eat some cash to make it happen.
Other trades of this type:
2009: Toronto Blue Jays trade Roy Halladay to the Philadelphia Phillies for Kyle Drabek, Travis d'Arnaud and Michael Taylor
2015: Atlanta Braves trade Andrelton Simmons and Jose Briceno to the Los Angeles Angels for Erick Aybar, Chris Ellis and Sean Newcomb
2017: Pittsburgh Pirates trade Gerrit Cole to the Houston Astros for Joe Musgrove, Michael Feliz, Jason Martin and Colin Moran
Saves are precious
1997: Seattle Mariners trade Derek Lowe and Jason Varitek to the Boston Red Sox for Heathcliff Slocumb
Contemporaneous quote: "The toughest part was giving up Cruz. I've said it before: If I had to give up young players to keep us in the pennant race, I'd do that. I did it the last two years, and I did it this year." -- Mariners general manager Woody Woodward, referring to the deals he'd made that day, including the Slocumb deal and one in which he traded Jose Cruz Jr. to Toronto for reliever Mike Timlin.
Rationalizing the indefensible: "Look, we're neck-and-neck with the Angels right now. Sure, one of us will probably get the wild card, but you can't count on that. It's a darned miracle we are where we are since our bullpen ERA is over 6. Now we have a proven closer at the back of the bullpen, and a proven veteran to set him up. Lowe has an ERA of almost 7 this season and while Varitek is a first-rounder and talented, we've got Dan Wilson behind the plate. I could not be happier about this trade."
Why it turned out bad: You could see this one coming from a mile away. The only thing Slocumb had going for him in 1997 was saves. At the time of the deal, he had a 5.79 ERA and a WHIP of 1.97. He was better after the deal and converted 10 of 11 save chances (albeit with a 4.13 ERA), but Timlin blew four of five save opportunities. Seattle still made the playoffs, but once there, the Mariners won a single game. Was it really worth it?
Lowe and Varitek went on to become core players on World Series-winning Red Sox teams. And Boston got them both ... for Heathcliff Slocumb. While Lowe had indeed struggled, Varitek was in fact a first-rounder who was knocking at the door of the majors at the time he was traded.
Lesson learned: Teams understand this now, but just in case they need a reminder: There is nothing precious about a one-inning reliever. Saves do not imbue one with magical immunity from stress during pressure situations.
Other trades of this type:
1993: Kansas City Royals trade Jon Lieber and Dan Miceli to the Pittsburgh Pirates for Stan Belinda
1998: Los Angeles Dodgers trade Paul Konerko and Dennis Reyes to the Cincinnati Reds for Jeff Shaw (included while acknowledging that Shaw was an effective closer for L.A.)
2016: Miami Marlins trade Chris Paddack to the San Diego Padres for Fernando Rodney