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Tom Verducci: Did Nationals give Stephen Strasburg too much money?
1:09 | MLB
Tom Verducci: Did Nationals give Stephen Strasburg too much money?
Tuesday May 10th, 2016

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On Tuesday, Nationals righthander Stephen Strasburg became the latest young star to agree to a long-term contract extension that buys out several of what would have been his post-free-agency seasons. In reaching a seven-year, $175 million extension with Washington, Strasburg joined a veritable All-Star team of players who were willing to delay their first shot at free agency in exchange for more immediate wealth and security from their current team. (See table below.)

More than just a trend, extensions for young stars have become the new way of doing business in baseball. After four decades of free agency, teams have finally realized that 25-year-olds are better investments than 30-year-olds. Meanwhile, as salaries continue on their ever-upward trajectory, waiting to accumulate six full years of service time to reach free agency represents an ever-larger gamble for players who know all too well that an injury or an unexpected drop in performance can wipe out the promise of an enormous payday.

Strasburg, having had his ulnar collateral ligament rupture once before, knows how quickly and unexpectedly that bubble can burst, which surely played a role in his becoming the rare Scott Boras client to forgo a chance at free agency, which he would have been eligible for this fall. His doing so delivered him instant security. It did the same for the Nationals, who not only have Strasburg locked up through 2019 in advance of an offseason that offers few viable free-agent starting pitching alternatives, but also have increased cost-certainty for the next three-plus seasons, which increases their ability to make other decisions about their roster and payroll going forward.

Before we get to the five players who could be next in line for an extension, take a look at just some of the top stars who are under contract for multiple seasons, many of whom also have club options attached to their deals.

 
Position Player, Team Signed Through
C Buster Posey, Giants 2021 (club option: '22)
1B Paul Goldschmidt 2018 (club option: '19)
2B Jose Altuve, Astros 2017 (club options: '18, '19)
SS Brandon Crawford, Giants 2021
3B Matt Carpenter, Cardinals 2019 (club option: '20)
LF Starling Marte, Pirates 2019 (club option: '20, '21)
CF Mike Trout, Angels 2020
RF Giancarlo Stanton 2027 (opt-out after '20; club option: '28)
SP Clayton Kershaw, Dodgers 2020

Now, here are the five top extension candidates among players who have yet to reach free agency, presented alphabetically.

Jake Arrieta, RHP, Cubs

Scheduled free-agency: After the 2017 season
Age at time of free-agency: 31

As a 30-year-old late-blooming pitcher, Arrieta isn’t necessarily an irreplaceable generational talent, but he is arguably the best pitcher in baseball right now. Last year's NL Cy Young winner is already earning an eight-figure salary via arbitration, which he will be eligible for again in January, so the Cubs won’t get away with a team-friendly contract such as the five-year, $38.5 million extension Cleveland gave Corey Kluber after his surprising American League Cy Young win in 2014. That five-year term sounds about right, but the guarantee would likely have to reach nine figures. An average salary of $25 million per season over five years would add up to a $125 million guarantee. That could be difficult for a pitcher with Arrieta’s history to turn down, even with Boras as his agent.

However, Arrieta recently told USA Today’s Bob Nightengale that he thinks he could get six or seven years upon reaching free agency after the 2017 season, likely envisioning a deal comparable to the six-year, $206.5 million pact the 32-year-old Zack Greinke just signed with the Diamondbacks. Given that, Chicago appears to prefer waiting until after the current season to negotiate with its ace, as the realities of following up his Cy Young performance over a full season could change the context of the conversation significantly.

Josh Donaldson, 3B, Blue Jays

Scheduled free-agency: After the 2017 season
Age at time of free-agency: 31

The defending AL MVP will turn 32 in early December of 2017, just a few weeks after he is due to hit the market. As with Arrieta, an extension for Donaldson would more closely resemble a free agent contract, both because it would take Donaldson deep into his 30s and because it would be building off the $17 million he’s due to make in his final year of arbitration via the two-year, $28.65 million deal he signed in February. However, Donaldson has a longer track record of success than Arrieta, having played at an MVP level in each of the last three seasons. Plus, as a hitter and an elite defender, he doesn’t carry the risk of collapse that accompanies every pitcher. As a result, it would likely take a guarantee in excess of $200 million to keep Donaldson in Toronto beyond next season. Indeed, given his elite play over the last three years, our What’s He Really Worth calculations would justify a contract closer to $300 million for Donaldson if he is able to sustain that level for the remainder of this season and next.

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The Blue Jays have more pressing concerns with Jose Bautista and Endwin Encarnacion both due to become free agents this fall, but Donaldson is their best player and only one more season away from being able to test the market. Toronto’s only real leverage against Donaldson is the uncertainty of his health and performance between now and next November. With Donaldson continuing to perform at his established level, the Jays would be wise to work out an extension with him as soon as possible, making sure they they have him locked up before making a large financial commitment to the 35-year-old Bautista. At 33, Encarnacion seems likely to be the odd man out in Toronto’s extension crunch.

Nick Wass/AP

Bryce Harper, RF, Nationals

Scheduled free-agency: After the 2018 season
Age at time of free agency: 26

Another Boras client, Harper seems determined to test free agency after the 2018 season. Already a perennial MVP candidate (and the youngest unanimous winner of the award in major league history last year), Harper will turn 26 in October 2018 and could become baseball’s first $400 million or even $500 million player that off-season. Harper will be worth that much if he stays healthy and continues to produce at his current levels. The question is whether or not there will be a team willing to spend that kind of money on a single player. That, plus the risk of a career-altering injury in the two-plus seasons remaining between Harper and his free agency, are the leverage the Nationals have to try to sew up up their superstar for less in the interim.

Of course, less money would likely still mean a contract comparable to, if not larger than, the record 13-year, $325 million extension Giancarlo Stanton signed with the Marlins in November 2014. That contract includes an opt-out after Stanton’s age-30 season in 2020, and a Harper extension would surely include a similar clause, as Strasburg’s also does. With Harper due for a massive raise via arbitration after this season and Strasburg already sewn up, Harper is now Washington's top priority.

•​ GALLERY: Every member of MLB's $100 Million Club

Eric Hosmer, 1B, Royals

Scheduled free-agency: After the 2017 season
Age at time of free agency: 28

The Royals have an impending disaster coming after the 2017 season when not just Hosmer, but also centerfielder Lorenzo Cain and third baseman Mike Moustakas will become free agents. Assuming their '17 options are picked up, closer Wade Davis​, shortstop Alcides Escobar, reliever Luke Hochevar, starting pitcher Kris Medlen, designated hitter Kendrys Morales and starter Edinson Volquez will also be on the open market, as could Ian Kennedy, another starter, if he uses the opt-out in his contract.

Hosmer is the youngest and very close to the best of that bunch, making him the team’s first priority in terms of extensions. A former No. 3 overall pick, Hosmer is a three-time Gold Glove winner who has been maturing at the plate over the last few seasons and is off to a hot start in this, his age-26 season, with a .949 OPS. Despite being yet another Boras client, Hosmer has nonetheless said that he is open to an extension if it would mean keeping together the core of the team that has won two straight American League pennants and last year's World Series. “If it was up to us, we’d like to keep it together as long as we could,” Hosmer told MLB.com in late February.

Meanwhile, Kansas City general manager Dayton Moore has said that he intends to try to sign as many of those impending free agents to extensions as possible. However, the financial realities make it seem unlikely that he will be able to keep them all. Moore was able to bring back free agent leftfielder Alex Gordon via a hometown discount last winter and unnecessarily extended catcher Salvador Perez as some sort of show of good faith. However, one wonders if Hosmer might need to see the Royals make additional commitments to the likes of Cain and Moustakas before agreeing to an extension of his own. The catch is that doing so could make it more difficult for Kansas City to find room in its budget to satisfy both Hosmer and Boras.

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Manny Machado, 3B, Orioles

Scheduled free-agency: After the 2018 season
Age at time of free-agency: 26

Machado is just three months older than Harper and is scheduled to reach free agency at the same time. Having survived two major knee injuries with no evident lingering effects, Machado is nothing less than one of the best all-around players in the game. He's an elite defender at third base who is just as viable at shortstop, and he continues to mature at the plate, all of which figures to keep him as a perennial MVP candidate in his own right (indeed, he already has two top-10 finishes).

Now into his arbitration years, Machado was a Boras client when he was drafted third overall in 2010, but he dropped Boras within months of signing with the Orioles and is now represented by Dan Lozano. That suggests that Machado might be more amenable to an extension than Harper or Arrieta. Indeed, in February Macahdo told the media that he hoped Baltimore would “keep me here for long term.”

“I know they’ve got the money for it,” Machado said, adding that the re-signing of Chris Davis to a franchise-record, seven-year, $162 million deal last off-season “brings me hope that they’re trying to keep everybody here and hopefully they will come up with something and we can make something happen.”

Given Machado’s youth and all-around ability, a nine-figure deal that would allow him to opt-out and test free agency at or around the age of 30 seems most likely.

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