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The Art of the Bad Deal

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Toronto Blue Jays v New York Yankees Photo by Adam Hunger/Getty Images

“Sometimes when I’ve got a ballplayer alone, I’ll just read Emily Dickinson or Walt Whitman to him. And the guys are so sweet, they always stay and listen. Of course, a guy’ll listen to anything if he thinks it’s foreplay. I make them feel confident, and they make me feel safe - and pretty. Of course, what I give them lasts a lifetime. What they give me lasts 142 games. Sometimes it seems like a bad trade, but bad trades are part of baseball.” – Bull Durham

Now that everyone is good and angry about the trade deadline, I thought I’d delve into baseball history to look at some of the worst trades every made, before everyone tries to put the crown on the Jays Front Office. One of the fascinating things about baseball history is just how often teams got it wrong, made mistakes, and allowed franchise altering players to go to another team for a few months of a relief pitcher or a corner infielder. Looking at the history, the thread that runs through how often the trades revolve around pitching; teams in the hunt for the play offs need it and will pay a premium for it

When making this list, I made the decision to not certain types of deals. The first are the blockbuster deals with five or six players from each team moving back and forth. After spending two hours working through six different possible ones, I found even the best and worst usually only involved a difference of 10 fWAR or so. I also eliminated some of the more famous obvious backroom dumping deals, especially between the Athletics and the Yankees in the 50s and the Spiders and the Browns in the 1890s, when ownership obviously colluded. In calculating the fWAR involved, I used the total fWAR of each players term with the team they were traded to in order to generate the total values.

11. Robinson for Pappas – 1966

While often cited as the worst trade of all time, bad enough to be included as a line in ‘Bull Durham’, the Frank Robinson trade is far from the worst mis-estimation of value in baseball history. In 1966, Cincinnati Reds GM Bill DeWitt decided that their struggling pitching rotation needed help and that they could trade some of their formidable offense for the arms that they needed. While Robinson was by far the most effective hitter on the team, he reported had a poor relationship with DeWitt, which is often cited as a possible motivation for offering him. In defense of the trade after, DeWitt famously quoted that Robinson was ‘not a young 30’. The Baltimore Orioles offered starter Milt Pappas, reliever Jack Baldschun and outfielder Dick Simpson for Robinson. The effects were immediate; Robinson had a career year at the plate in 1966, winning the Triple Crown and the MVP trophy, and led the Orioles to win the World Series.

The reason that this deal isn’t the travesty it is widely considered to be is that while Milt Pappas is largely forgotten today, the right hander had an excellent 17 year career, including a big resurgence near the end of his career with the Cubs. He had two solid seasons starting for the Reds before struggling and being traded to the Braves in 1968. Baldschun and Simpson were busts and both men were out of baseball within four years.

Total: 33.5 fWAR – 7.5 fWAR = +26 fWAR Baltimore

10. Bautista for Diaz – 2008

In an essentially nothing deal in late August 2008, the Pirates and Jays swapped a couple of unremarkable players. Robinzon Diaz, another casualty of the Jays ‘Catcher of the Future’ title was traded to Pittsburgh for an often-traded platoon player named Jose Bautista. Diaz was our number 11 prospect at the time but had already been passed on the depth chart by JP Arencibia. Fangraphs thought the deal was hugely lopsided in favour of Pittsburgh, seeing Diaz as potentially a solid MLB level catcher and Bautista as little but insurance off the bench for the injury prone Rolen.

Diaz would play 42 games over two years with the Pirates before spending the rest of his career bouncing around other systems high minors without getting another call up. Bautista would be largely as advertised until the end of 2009, when he belted 10 home runs in September. The skipper Cito Gaston was quoted saying he saw a lot more upside in Bautista and committed to a full time role in time for him to hit a league leading 52 homers in 2010 and emerge as one of the best offensive players in baseball for the next eight seasons.

Total: 36.3 fWAR - -0.3 fWAR = +36.6fWAR Toronto

9. Brock for Broglio – 1964

Another of the most famous bad trades in baseball is the Chicago Cubs dealing future Hall of Famer Lou Brock to St. Louis for pitcher Ernie Broglio. The deal is often cited as one of the worst in baseball history and the Emil Verban Society awards a yearly ‘Brock-for-Broglio Judgement Award’ for bad decision making by political and business leaders. The Cubs had bend treading water at .500 in June, looking to bolster their weak pitching. At the time, Chicago had been employing their ‘College of Coaches’ approach, with 8 coaches working in tandem without a manager. 24 year old Lou Brock was scuffling in right field in his fourth major league season. He referred to his troubles later being connected with the coaching approach, where different coaches would offer him conflicting advice and expectations.

Ernie Broglio had led the National League in wins in 1960 and had put up 18 wins the season before with the St. Louis Cardinals. When the Cubs approached the then 8th place Cardinals about Broglio, it was Manager Johnny Keane who pushed for the return to be built around Brock. The final deal was Lou Brock, Jack Spring, and Paul Toth for Ernie Broglio Bobby Shantz, and Doug Clemens. When the deal was announced, the Chicago press overwhelmingly praised the canniness of John Holland, the Cubs GM for trading away busted players for a top 20 pitcher. Public opinion quickly turned as Broglio struggled and suffered nerve damage in his pitching arm. Clemans would have a career high season with the Cubs in 1964, but his offense collapsed the next year and Bobby Shantz pitched just 11 innings of work before retiring at the end of the next season. Toth and Spring were non-factors, with Toth assigned to AAA and Spring pitching just 3 innings. Brock would have one of his best seasons, lifting the Cardinals to crawl up the standings and win the World Series by the end of the year.

Total: 39.2 fWAR - -2.1 fWAR = +41.3 fWAR St. Louis

8. Abreu for Stocker – 1997

At the end of the 1997, following a loss in the NLDS, the Houston Astros left promising young outfielder Bobby Abreu unprotected in the expansion draft for the new Tampa Bay Devil Rays franchise. Tampa Bay snapped up Abreu, but surprisingly, dealt him quickly to the Phillies for shortstop Kevin Stocker. Stocker was a light hitting, defensively challenged shortstop who seemed to have parleyed a great rookie season into a reputation as a solid player. Already declining, Stocker’s offense and defense collapse on his arrival in Tampa Bay for the 1998 season. Meanwhile, Abreu would emerge as one of the elite offensive outfielders over the next 8.5 seasons with the Phillies before being dealt to the Yankees in 2006.

Total: 47.1 fWAR – 2.3 fWAR = 44.8 fWAR Philadelphia

7. Colon for Phillips, Sizemore and Lee – 2002

The remarkable trade between the Cleveland Indians and the Montreal Expos for Colon in 2002 came in the midst of a storm of circumstances. At the time, the Expos were being operated by the MLB and, with the Minnesota Twins, in consideration to be removed from the league. Loria, the former owner, had taken all of the data about the Expos organization with him when he was awarded the Marlins, leaving the team with only the physical printouts and files they had on hand about their own systems and the knowledge of the scouts and coaches not poached by Loria. Still, at the time of the deal, the Expos were 6.5 games behind Atlanta in the division and looked like they were in position to make a run. GM Omar Minaya strongly felt that a playoff run might ignite interest in Montreal, reviving the possibility of a new ownership group and a new stadium to keep the team there.

Enter Mark Shapiro. The then 34 year old GM was keenly aware that the end of Cleveland’s excellent run through the late 90s was coming to an end and was looking to inject young talent into his system to transition to a new contending group of players. Bartolo Colon was the ace of the staff, set to enter free agency at the end of the year. When Minaya started to inquire about pitching, Shapiro had a secret weapon to use in trade talks: Tony LaCava. LaCava had been the director of player development for the Expos before joining Cleveland. With Loria’s looting of the team’s databases, LeCava knew more about the Expos prospect than their own Front Office did. The final deal was Bartolo Colon and Tim Drew for Lee Stevens, Brandon Phillips, Grady Sizemore, and Cliff Lee.

Colon continued to pitch extremely well, but the Expos faltered following the trade, finishing a distant second to Atlanta. For Cleveland, most of the value came from the emergence of Lee as a starter and Sizemore’s run as one of the best outfielders in baseball until injuries derailed his career.

Total: 2.3 fWAR – 51.2 fWAR = +48.9 fWAR Cleveland

6. Johnson for Langston – 1989

Mark Langston was one of the best pitchers in the game when he was dealt to Montreal. He’d already turned down a $7.1M contract extension in Seattle, a team dealing with obscurity. In making the deal, all the spotlight was on him, with Boston and Los Angeles involved in discussions. The haul for Seattle was about acquiring pitching prospects to replace Langston once the contract extension failed.

Langston was a beast for Montreal. Paired with Dennis Martinez, they dominated the National League. Unfortunately, the offense failed them, leaving the team with a perfect .500 season. Johnson would go on to turn into the dominate left-hander for Seattle, Brian Holman and Gene Harris did little to change the calculus of the deal. Johnson would pitch for Seattle for 10 years, turning himself into a Hall of Famer in the process.

Total: 51.8 fWAR – 2.7 fWAR = +49.1 fWAR Seattle

5. Bowa, Sandberg for Iván DeJesús – 1982

The Phillies were a dominant ball club in the late 70s and early 80s, with a World Series win and 6 division titles. But their farm was shaky and at the end of the 1981 season, they were looking at an aging core of players. Embroiled in a contract dispute with long time shortstop Larry Bowa, they decided to resolve the situation by trading him to Chicago for their starting shortstop Ivan DeJesus. DeJesus was a great defender with a ton of speed, but like a lot of speedy players at the time, couldn’t hit and was caught stealing too often to be more valuable. At the time, he was still considered a big asset and the Phillies had to negotiate former Phillies manager and now Cubs GM Dallas Green down from his request of Luis Aguayo. Eventually, they through in a SS prospect named Ryne Sandberg.

DeJesus would have three seasons with Philadelphia, mostly maintained his light hitting profile. Bowa would have one solid season for the Cubs in the midst of four mostly dismal years. Ryne Sandberg was immediately switched to second base, where he would play for 16 seasons with the Cubs and eventually be voted into the Hall of Fame.

Total: 60.6 fWAR – 2.1 fWAR = +58.5 fWAR Chicago

4. Alexander for Smoltz – 1987

In 1987, the Tigers were deep into another playoff run, behind the Jays in the race. They had been long interested in a pitcher that had been a regular thorn in their side for Baltimore, New York, and the Jays just the year before: Doyle Alexander. Alexander had been traded to Atlanta midway through the 1986 season, and despite a mediocre start, was still coveted by Detroit as exactly the right kind of big game starter to pair with Jack Morris in their rotation. While still considerably back in the division in August, the Jays went into a swoon while Alexander pitched like the ace they expected. They fought the Jays to a tie and a one game playoff into the post season, which Detroit won. Unfortunately for them, they ran straight into a Twins team that had just gotten hot and lost the Pennant.

Meanwhile, John Smoltz would spend the next 19 seasons as part of one of the greatest pitching rotations in baseball history. Tom Glavine, John Smoltz and Greg Maddux combined as the ‘Big Three’ to dominate baseball and win thirteen division titles. Smoltz had Tommy John surgery in 2000, which forced him to move to the bullpen, becoming the Braves closer, replacing human filth John Rocker. Smoltz would record 154 saves in just four years before returning to the rotation.

Total: 78.2 fWAR – 6.8 fWAR = +71.4 fWAR

3. Anderson for Bagwell – 1990

In 1990, the Red Sox were battling the Jays for the division title. Boston had a loaded offense and a powerful rotation fronted by Roger Clemens. But the bullpen was a glaring weakness for them. Trading for Larry Anderson of Houston was acquiring the best arm on the market at the very end of the trade period, but it meant the Red Sox had to move a real prospect. Instead of prospect Scott Cooper, who was the gem of their system at the team, Houston cued into Jeff Bagwell’s excellent offensive numbers, including his ability to lay off pitches out of the zone and demanded him in the trade.

Anderson immediately paid off for the Red Sox. In the month he was with the team, he spun 22 innings in 15 appearances, and struck out 29 percent of hitters against a walk rate of only 3.5 percent. He was a key piece in holding off the Jays and making it to the post-season. But a white hot Oakland Athletics dismissed the Red Sox in four game. Meanwhile, Bagwell was shifted to first base for the bulk of his 15 year career with Houston, becoming an elite player and eventually being elected to the Hall of Fame.

Total: 80.2 fWAR – 1 fWAR = +79.2 fWAR Houston

2. Rusie for Matthewson – 1900

The freewheeling business rules of the late 19th and early 20th century created one of the most egregious examples of ‘inside baseball’ in terms of owners working the system for their own maximum return. Amos Rusie had been one of the most dominant pitchers in baseball for the last eight years before the trade. But he had a secret that he only shared with his owner, Andrew Freedman; his arm was hurt and failing. Freedman was in the midst of financial issues and was in discussions with the owner of Cincinnati Reds owner John Brush about the sale of the Giants to him. Brush agreed to trade a prospect for the Hoosier Thunderbolt. New York dailies lamented the trades, one going as far to opine that “The Giants without Rusie are like Hamlet without the Melancholy Dane.”

A few months later, the sale of the Giants to John Brush reunited him with his prized prospect, Christy Mathewson. Mathewson started strong, but it was in 1902 when McGraw joined the Giants and would be there for Christy’s ascension to baseball’s elite pitching. McGraw considered Mathewson the greatest pitcher he’d ever seen and Christy didn’t disappoint. While Rusie pitched just three games for the Reds before retiring, Mathewson’s Hall of Fame career would last 17 seasons before the First World War and gas damage to his lungs would end his baseball career and shorten his life. Mathewson would have one final important moment in baseball history, as the player advisor that helped discover the game fixing behind the 1919 World Series.

Total: 0.2 fWAR – 90 fWAR = +89.8 fWAR New York

1. Ruth for Cash – 1920

You can quibble if you want that Ruth was sold rather than traded but regardless, resources moved in one direction for a player in the other. The Babe was already a tremendous player; about to break the total home run record while still being an excellent left-handed pitcher. But Harry Frazee was an entrepreneur, theatre producer and man who looked towards what would further his interests. When he bought the Red Sox for a song in 1916, he was inheriting a championship calibre team. He would spend the next several years dismantling it and selling it off for as much as possible. Frazee was engaged in an ongoing feud with American League President Ban Johnson and was limited by league rules to how he could run the club while Johnson worked behind the scenes to try and yank the club from him.

While the ‘Curse of the Bambino’ like to circulate the story that Ruth was sold to finance ‘No No Nanette’, the truth is significantly more complicated. Johnson limited Frazee’s negotiation options to Chicago and New York. Eventually, they made a deal to sell Ruth to Ruppert’s Yankees for $100,000 USD, paid over four years with 6% interest. So Ruth’s final tab was $110,000 USD. Ruppert also agreed to cover the financing for $300,000 USD for Frazee’s shows, a kind of insurance against a flop.

Regardless of the circumstances, the $110,000 is about $1.3M USD in modern currency. Against the current value of fWAR, the amount the Yankees spent would be now valued as about 0.1 fWAR. The Babe generated 150 fWAR in his career with the Yankees. In Ruth’s final year, the washed up slugger generated just 5.2 fWAR. He’s the only player to have 9 +10 fWAR seasons. For anyone who wants to talk about the greatest player in baseball history, several have dominated the game. Babe Ruth is the only one who fundamentally changed how it was played due to his ability.

Total: 150 fWAR – 0.1 fWAR = +149.9 fWAR New York