They're not all bad: The best nine-figure deals in recent baseball history

Schilling Weighs In On Stanton's Megadeal

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With Giancarlo Stanton's record-breaking 13-year, $325 million contract (really a six-year, $107 million deal with a giant player option) has come a fair amount of skepticism and the typical insistence that long-term contracts in baseball never work.

There's certainly merit to that point. There have been far more misses than hits on nine-figure deals, especially ones given to players on the wrong side of 30.

But despite popular belief, not every expensive contract has been a disaster. For the sake of contrarianism, here are the five nine-figure deals that have worked out best for the teams offering them, plus some honorable mentions.

Honorable mention:

CC Sabathia's seven-year, $160 million deal (signed at age 29) went great for the Yankees for four years (prompting a regrettable one-year extension) before the lefty struggled in 2013 and got injured in 2014. Still, Sabathia pitched New York to a World Series title in 2009 and has put up 21.6 WAR in pinstripes, so the Yankees almost assuredly view the original contract a success.

Matt Holliday has two years left on the seven-year, $120 million deal he signed with St. Louis in 2010 (at age 30), and it's gone well for the Cardinals thus far. The left fielder has averaged 24 home runs and four WAR per season, with a .295 batting average, .879 OPS and 141 OPS+. As long as 2015 and 2016 aren't disastrous, this deal will look pretty good when it's over.

If we're willing to look just below the $100 million threshold, we see more long-term deals that proved bargains for the clubs. Chipper Jones' six-year, $90 million Braves contract inked in 2001 paid off, as did the Cardinals' eight-year, $90 million agreement with Scott Rolen in 2003. In 2002, the Giants secured Barry Bonds for five years, $90 million and were rewarded with 167 home runs, a 1.273 OPS and 36.1 WAR.

But restraining our parameters to contracts worth nine figures, these are the best long-term deals ever signed.

5. Carlos Beltran, Mets (traded to Giants)
Years: 2005-11
Age: 27
Terms: Seven years, $119 million
WAR during contract: 32.3
Dollars per WAR: $3.68 million

Mets fans were never quite satisfied with Beltran during his time in Queens, but production-wise the center fielder was well worth his contract.

Analysts estimate that during the time period of Beltran's deal, the value of a win above replacement on the open market was between $4 million and $5 million a win (today it's closer to $6 million or $7 million). By that measure, Beltran earned substantially more than his $119 million contract.

He performed well by traditional measures as well, batting .282 with an .872 OPS (and 126 OPS+), averaging 31 doubles and 22 home runs and winning three Gold Glove awards, despite battling injuries. He provided the Mets value even in departure, fetching promising starter Zack Wheeler in a trade late in the final season of his deal.

If the Mets and their fans were expecting more from Beltran during his time in Queens, they shouldn't have been. He played the best years of his career there and clearly justified the money he made.

4. Manny Ramirez, Red Sox (traded to Dodgers)
Years: 2001-2008
Age: 28
Terms: Eight years, $160 million
WAR during contract: 36.6
Dollars per WAR: $4.37 million

Relations between Manny and the Red Sox went south toward the end of his big deal, but overall what was at the time the biggest deal in history went pretty smoothly for both parties.

Ramirez finished in the top 10 in MVP voting each of his first five years in Boston and belted 291 home runs during the length of his contract, which wrapped up with the Dodgers. The Red Sox won two World Series with Ramirez they would not likely have won without him, with Manny winning Series MVP in 2004.

Ramirez remains a beloved figure in Boston, and any Red Sox fan would happily repeat the deal that brought him there.

3. Derek Jeter, Yankees
Years: 2001-10
Age: 27
Terms: 10 years, $189 million
WAR during contract: 41.1
Dollars per WAR: $4.6 million

At the time, this was the second-biggest contract in baseball history, but given Jeter's popularity, durability, consistency and age at the time, it never posed too big a risk.

As it turned out, Jeter almost certainly lived up to the deal on the field, averaging more than four WAR (according to baseball-reference) per season despite his shaky defensive metrics during the period.

He finished in the top 10 in MVP voting four times during the contract (and eleventh once) and in 2009 had one of his best seasons while captaining the Yankees to a World Series title.

And regardless of whether Jeter's play entirely justified his deal, there's no question his marketability made his presence worth the Yankees' while throughout this 10-year period.

2. Alex Rodriguez, Rangers (traded to Yankees)
Years: 2001-2010
Age: 26
Terms: 10 years, $252 million
WAR during contract: 71.4
Dollars per WAR: $3.53 million


The player currently most associated with his awful contract actually once signed one of the most team-friendly, long-term deals in baseball history.

Had A-Rod played out the original ten-year contract he signed with Texas in 2001, the deal would have been considered an overwhelming success. He made the All-Star Game every year but one, won three MVPs -- one for the Rangers, two for the Yankees -- and finished in the top 10 in voting seven times, while averaging more than seven WAR per season.

The trouble came when A-Rod opted out after his MVP 2007 season and the Yankees handed him $275 million over 10 years. Rodriguez was 32 at the time, and that deal never had a chance. Somehow, he still has three years left.

If we only count the seven pre-opt-out years on Rodriguez's original contract, it looks even better than if we consider all 10. Over those seven years, he was paid $158.4 million to accumulate 56.3 WAR (or a remarkable eight WAR per season).

A-Rod himself represents both sides of the big-contract ledger. Long-term contracts given to players in their early-30s (like A-Rod's second contract) don't usually work, but ones extended to those in their mid-20s (like his first) often end up looking awfully good.

1. Albert Pujols, Cardinals
Years: 2004-10
Age: 24
Terms: Eight years, $116 million (including team option for last year)
WAR during contract: 65.7
Dollars per WAR: $1.77 million

The Cardinals paid Pujols nine figures and got a complete and utter steal.

During his contract, the first-baseman posted an OPS of 1.042, hit 331 home runs, averaged 8.2 WAR a year, won three MVPs and finished in the top 10 of voting every single year of the deal.

In that period, the Cardinals won three pennants and two World Series, and Pujols became the franchise's most iconic player since Stan Musial. Unlike almost every other contract on this list, this one continued yielding results all the way to its conclusion, when Pujols hit three home runs in a World Series game and St. Louis took the title. The deal was an unqualified success.

Pujols' agreement was awfully similar in principle to the one the Angels gave Mike Trout last year and to Stanton's deal pre-opt-out. The idea was to buy out the player's last few arbitration years and some free agency as well, securing him through essentially his entire peak.

It's the standard of all long-term contracts and the best-case scenario for Stanton's deal and all others like it.

Alex Putterman is a junior Journalism major at Northwestern University and sports editor of the Daily Northwestern student newspaper. He has fairly eclectic interests but loves baseball above all. Follow him on Twitter: @AlexPutt02
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