Weekly Rotation: The five worst $100M contracts in MLB history
It’s been nearly six years since Ryan Howard signed a $125-million extension with the Phillies on April 27, 2010 to keep him in Philadelphia through 2016. The deal has not panned out, as the burly first baseman began his rapid decline right as the extension kicked in before the 2012 season.
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Howard seemed destined to fade into the background of the MLB landscape this year, merely deployed as an expensive platoon partner for the mediocre (at best) Phillies. Instead, beloved Dodgers broadcaster Vin Scully decided to take aim at the expensive veteran over the weekend after Howard tied Joe DiMaggio on the all-time home run list.
Since every delectable Scully sound bite has been magnified this season, his final in the booth, Howard was unceremoniously thrust back into the spotlight. Does his play truly merit such derision? The Weekly Rotation, our data-driven weekly column, aimed to figure that out.
To determine where Howard ranks among his fellow $100-million peers, I calculated how much each team paid per 1.0 Win Above Replacement (WAR) over the course of every nine-figure deal in MLB history. The “salary per 1.0 WAR” figure used here isn’t a perfect calculation for active contracts, since the players haven’t played the entirey of the contract yet. In those cases, I used a contract’s average annual value (i.e. $100 million / 5 years = $20 million).
You’ll see that teams below are paying $23 million, $42 million and even higher for a single Win Above Replacement. To give some context to that: Last season’s leader, Bryce Harper, had 9.5 WAR and the Washington Nationals paid him $2.5 million.
Interestingly enough, all five entries on this worst-of list are contracts for left-handers. Perhaps teams are willing overlook the flaws of some southpaws to possess the specialized talent they embody. As for Howard? We’ll see below if Scully is backed up by the numbers.
Notes: Contracts must have at least three seasons complete to be eligible, and 2016 stats were not taken into account.
5. Carl Crawford (2011-17), Red Sox
Salary per 1.0 WAR: $23.1 million
Contract details: 7 years, $142 million
WAR over contract: 4.4
Some might not expect Crawford to land in the bottom five of baseball’s $100-million men. But the man who led the majors in triples and stolen bases four times with Tampa Bay has been sapped of his speed by Father Time, rendering him an average player, at best.
He recorded a -0.1 WAR last year with the Dodgers and looks unlikely to start regularly again in Los Angeles. His salary-per-WAR figure only figures to increase over the final two years of his deal.
4. C.C. Sabathia (2012-16), Yankees
Salary per 1.0 WAR: $23.2 million
Contract details: 5 years, $122 million
WAR over contract: 4.2
Sabathia’s first mega-deal with New York, a seven-year, $161 million commitment signed before the 2009 season, actually turned out quite well for the Yankees. It was a five-year extension signed midway through that contract that’s proven to be an albatross, as Sabathia has struggled to overcome issues on and off the field over the past few years.
[Elsewhere: Jeffrey Loria gives Dee Gordon some serious bling for batting title]
Once a durable workhorse whom you could annually count on for 200 innings and a sub-3.50 ERA, Sabathia recorded a 4.81 ERA while averaging 141.1 innings between 2013-2015. He hasn’t looked any better this year, despite admirably seeking help for his alcoholism last fall.
Like Howard, Sabathia is only under contract through the end of this season. The Yankees will have to pay him a $5 million buyout for 2017, however.
3. Mike Hampton (2001-08), Rockies
Salary per 1.0 WAR: $40.3 million
Contract details: 8 years, $121 million
WAR over contract: 3.0
Hampton parlayed a fantastic 1999 campaign, in which he led the NL with a 2.90 ERA, and a successful 2000 postseason run with the Mets into the largest contract in sports history (at the time). Needless to say, the Rockies, always desperate for pitching due to their bandbox home field, massively overpaid.
The southpaw recorded a 5.75 ERA in two disastrous seasons in Colorado before finishing out the deal in Atlanta, where he was better but never made another All-Star team. At least he held his own in the batter’s box, winning three Silver Slugger awards during the contract.
2. Barry Zito (2007-13), Giants
Salary per 1.0 WAR: $42 million
Contract details: 7 years, $126 million
WAR over contract: 3.0
The famously chill Zito was beloved across The Bay Area during his time with Oakland, where he won a Cy Young Award and made three All-Star teams. But Zito admitted his landmark deal, the largest given to a pitcher at the time, placed pressure on him as a Giant. Sharply declining velocity also didn’t help his cause.
[Elsewhere: Milt Pappas, famous for near-perfect game with Cubs, dead at 76]
He did earn some redemption by pitching effectively during San Francisco’s run to the 2012 World Series, as the Giants won his final 14 starts, including Game 1 of the Fall Classic.
1. Ryan Howard (2012-16), Phillies
Salary per 1.0 WAR: $?!?
Contract details: 5 years, $125 million
WAR over contract: -3.0
As the only $100M man to accumulate negative WAR over the course of his deal, Howard broke our arithmetical system for ranking these contracts.
The general manager who gave it to him, former Phillies exec Ruben Amaro Jr., is now a first-base coach for the Red Sox since he presumably could not find front-office work following his stint in Philadelphia. This contract certainly contributed to that epic demotion.
Howard is the final remnant of the Phillies “dynasty” that won a World Series title in 2008, returned to the championship in 2009, then failed miserably to replicate those triumphs during the 2010s. Sometimes a taste of success can make men do crazy things.
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Will Laws is a writer for PointAfter, a sports data aggregation and visualization website that’s part of the Graphiq network. PointAfter is a platform for shot charts, scatter plots and other data visualizations about MLB players, NFL teams and dozens of other topics. Follow him on Twitter, @WillLaws.
