If there’s a pitfall to success, it’s that sustaining it bears a financial burden. In baseball, almost universally, the teams that are most successful boast underpaid players that exceed the expectations of their contracts.
Cubs ace Jake Arrieta, among Major League Baseball's most underpaid pitchers, epitomizes that paradigm. The right-handed Arrieta carried the Cubs through much of the second half of the season and ended his 2015 campaign with a major league-best 22 wins and a 1.77 ERA.
The Cubs will eventually sign Arrieta to a lucrative, long-term deal. But when?
Both sides would benefit from doing so right now.
The Theo Epstein era in Chicago as Cubs president of baseball operations has been earmarked by an overhaul of the organization’s minor league system. Young, homegrown players like Kris Bryant, Kyle Schwarber and Addison Russell, all major contributors in 2015, are still under team control and, therefore, playing on bargain-basement deals. Their time to be paid will come later.
For Arrieta, it’s now.
Unquestionably, Epstein and Co.’s trophy transaction was trading for Arrieta, reliever Pedro Strop and cash in exchange for pitcher Scott Feldman and catcher Steve Clevenger (Feldman was the top-paid player on the Astros last season. In 2015, Clevenger hit .287 in 105 games for the Orioles).
Arrieta, a player who has yet to land a big deal, is looking for the kind of transformational wealth a long-term deal provides. Injuries and control issues stymied the start of the 29-year-old Arrieta’s career. So he has yet to cash in on the type of contract his 2015 statistics might otherwise suggest. But now, by any statistical measure, Arrieta is one of baseball's best pitchers.
And, arguably, its biggest bargain.
In 2015, Arrieta was second among all pitchers with a 7.6 WAR and won the 2015 National League Cy Young Award. He made $3,630,000 last season, according to Cot's Baseball Contracts, costing the Cubs an astoundingly low $497,260.27 per win above replacement.
By comparison, the other four pitchers in the league's top five in WAR were Clayton Kershaw ($3,787,375.47 per win above replacement), David Price ($3,085,937.50 per win above replacement), Max Scherzer ($2,678,571.41 per win above replacement) and Chris Sale ($1,397,849.52 per win above replacement).
Arrieta has two years of arbitration remaining on his contract and is set to become a free agent before the 2018 season. The Cubs will never have more leverage in negotiations. The closer Arrieta gets to free agency, the more he will be willing to wait and test the open market.
So now would be the time to offer Arrieta a team-friendly deal that would simultaneously give the Cubs ace security.
A pitcher’s arm is baseball's most fragile commodity. There’s no determining who might become seriously injured or why.
For example, White Sox ace Chris Sale looks like his elbow is about to pop out every time he throws. He hasn’t had serious arm surgery. Former Cubs pitcher Mark Prior was said to have perfect mechanics. His once-promising career ended early as a result of injury.
Testing the open market would require Arrieta to gamble on the unknown.
To command a contract that would pay him $25 million-$30 million per year, Arrieta would need to replicate his 2015 season in 2016 and 2017. Impossible? No. It may even be likely, considering how much he improved in 2015.
But it only takes one pitch to derail the career of a star hurler. One bad movement could mean Tommy John surgery, a torn labrum or any of the litany of arm injuries that can alter the trajectory of a promising career.
Arrieta has to weigh the upside of waiting, which may not justify the risk given his age.
He wouldn’t become a free agent until he was 31. His birthday is March 6, so he will actually turn 32 before the beginning of the 2018 season. By that age, teams would be less willing to offer Arrieta a longer deal.
If Arrieta were to accept a deal now and he continues to prove he has top-of-the-rotation stuff, then he could potentially sign another lucrative contract similar to the one 37-year-old John Lackey signed this offseason—a two-year, $32 million deal with the Cubs, according to ESPN.
What might a team-friendly deal look like?
There are many ways contracts can be structured. But a deal that pays Arrieta no more than $20 million per year could potentially save the Cubs at least $5 million per year should Arrieta continue as one of baseball’s best pitchers. Over the course of a six-year deal, that could pay him as much as $120 million. The deal could be front-loaded and include an opt-out, vesting option or other player-friendly clauses.
His value might never be higher.
It always seems in these negotiations that there is one side that has overwhelming leverage. Like any team and player approaching potential contract talks, the Cubs and Arrieta are on divergent roads.
Lucky for both sides that, right now, they intersect.
Seth Gruen covers Major League Baseball for Bleacher Report. Follow him on Twitter @SethGruen.
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