Beyond Cost Certainty

The number of early career contract extensions is on the rise while outcomes vary wildly

There are sacred thresholds in baseball that we grew up on: 20 wins, 3,000 hits, .400 batting average, 500 homers and so on.

There is also six years of Major League Service (MLS), the amount of time in the big leagues that a player must achieve to reach free agency.

Generally speaking, during the first three seasons of a player’s career, his salary is at or around league minimum ($570,500 in 2021). During the ensuing three seasons, the player is arbitration eligible, and his salary is determined by negotiations rooted in the framework of comparable players of similar service time in recent history.

Most players who arrive at free agency do so having played each of their first six seasons on one-year contracts. Every so often, though — and more now than ever — teams and players are reaching multiyear agreements well before the need ever arises.

What’s the hurry?

There are plenty examples of players already into their arbitration years who sign multiyear extensions that “buy out” arb years and include a year or two of would-be free-agent years. The player sacrifices earning upside for guaranteed security, and the club assumes the risk in exchange for an extra year or two of the player’s services under expected market value.

In recent years, however, more players are signing long-term deals in their pre-arbitration seasons. Most recently, Angels leadoff hitter David Fletcher signed a five-year, $26 million deal that covers his final year of pre-arbitration, all arb years, and one year of free agency. The Angels also hold club options in 2026 and 2027.

We’ve already covered the peculiar extension of Twins pitcher Randy Dobnak, who had a poor start to the season but today was recalled from Triple-A St. Paul to make tonight’s start, and the record-breaking contract agreed upon by the Padres and Fernando Tatis Jr.

What I’ve begun wondering about is if there’s anything we can learn from specific front offices based on the players they proactively invest in.

John Hart, who served as general manager for the Indians from 1992-2001, introduced an aggressive approach in signing players to long-term extensions in a creative — and successful — attempt to retain talent in the small market of Cleveland.

Sandy Alomar Jr. and Carlos Baerga were the first two players to receive multiyear contracts during their arbitration years that, consequently, provided great value to the Indians during free agent years. It allowed Hart and the Indians to retain those players and, later, guys like Omar Visquel, Jim Thome, and Manny Ramirez through similar deals.

Hart’s daring served as a guiding light for future executives. His temerity and skill was groundbreaking. It set him apart from his peers. After all, we are still referencing him nearly 30 years later. I think it has also become an aspirational standard for many baseball executives: to display superior negotiation and evaluation skills through pre-arbitration contract extensions.

It Started In Tampa

In April 2008 — not even one full week into his Major League career — the Tampa Bay (Devil) Rays inked Evan Longoria to a six-year, $17.5 million contract with three club options to turn the deal into a nine-year, $44 million agreement.

Evan Longoria is under contract through 2022, after which he may face free agency for the first time in his career. (Suzanna Mitchell/San Francisco Giants)

With Tampa, it’s easier to get to the bottom of their thinking. Their small-market payroll can only withstand so much. Longoria was the AL Rookie of the Year in 2008, and by the time his first three seasons had concluded, he was a three-time All-Star and two-time Gold Glove winner. The Rays saved themselves millions of dollars with the deal, and they positioned themselves to retain his services for five years longer than had he approached free agency after his sixth season.

Well, Houston took notice and, in 2014, awarded prospect Jon Singleton a five-year, $10 million extension before his first Major League game. Singleton had served a 50-game suspension for a second failed drug test in 2013. He was open about his struggles with marijuana, but the Astros were undeterred. The contract had the potential to span eight years and pay $30 million if Houston exercised club options.

In 2014 and 2015, he combined to hit .171 with an OPS of .621 and a WAR of -0.9. On October 2, 2015, at the age of 23, Singleton played in his final big league game. He didn’t stick around long enough to listen for the banging of the trash cans. He received his $10 million nonetheless.

Longoria and Singleton established the points on either end of the risk/reward spectrum. What’s notable is that some of the Union hawks spoke out against Singleton’s deal when it was signed.

Mark Mulder @markmulder20

Just saw contract this #astros prospect signed. Either he doesn't believe in himself to be great or he has a terrible agent who wants the 4%

Two-time All-Star pitcher Mark Mulder didn’t like it, but it turned out to fetch Singleton about 10 times more than he would have received otherwise.

I was a part of the Diamondbacks front office that signed Paul Goldschmidt to a five-year contract prior to his second full season in 2013. The terms of the deal began in 2014, his final year before arbitration eligibility.

The pact turned out incredibly well for the D-backs; Goldschmidt finished in the top five of NL MVP voting three times between 2013-2017.

There were even moments when Goldy sympathizers within the office brought up the idea of adding years and dollars onto the contract to make it more equitable. While that didn’t happen, the Cardinals have since taken very good care of him.

With more and more clubs and players reaching accords before arbitration years, I want to explore what we can learn about the teams behind these deals. Surely, it must be for reasons other than the chance to declare “cost certainty.”

Next week, we’ll look at some of the most aggressive extensions, including the deals the Phillies made with Scott Kingery, the Mariners made with Evan White, and the White Sox made with Eloy Jimenez. What do all three have in common? Each signed six-year guaranteed contracts with multiple club options before his first day in the big leagues.

Approaching 20,000

On Wednesday, two players made their Major League debuts: Cubs first baseman P.J. Higgins and A’s center fielder Luis Barrera. Neither player accomplished anything of significance, but they did get us two players closer to 20,000.

Higgins and Barrera were the 19,996th and 19,997th players in Major League Baseball history. I don’t believe there’s any reward for being the 20,000th player — no balloons falling from the ceiling, no sirens, no shopping sprees, no cash reward.

It’s taken 150 years to get to this point, and — as we discussed a couple months ago — expanding rosters limits and COVID-related roster exceptions accelerated the pace. While nothing more than an arbitrarily satisfying threshold, I am curious to see who number 20,000 will be. (The late Mark Belanger was the 9,999th player to make his debut. Andy Kosco was the 10,000th. Both of those gentlemen debuted in August 1965.) Any guesses?

A Friend and A Scout

Clay Daniel passed away on May 3 at the age of 58. I worked closely with Clay during my time with the D-backs. At the recommendation of Kevin Towers, we hired Clay as a pro scout and gave him what amounted to a second chance in the game. Clay was a great scout who loved being around baseball and baseball people. He was always one of the first at the ballpark, and he always had a smile on his face. Clay was boisterous, raucous and uninhibited. Like him or not, he was always himself. When it came down to it, the man could scout.

We crossed paths in Harrisburg in April 2015. There was a blue-chip starting pitching matchup between Zach Eflin of the Phillies (Reading) and Joe Ross of the Nationals (H-burg). In the 2nd inning, Eflin unintentionally yanked a first-pitch fastball behind a hitter. The ump immediately ejected him. It was atrocious judgment by a Double-A umpire.

Well, Clay let him hear about it. In his higher-pitched sing-songy voice, Clay was impossible not to hear. I can’t remember all the words, I can’t remember if the children’s ears needed to be covered, but I’ll always remember the visceral feeling of being seated next to him as he unloaded. It was passionate, entertaining and highly questionable. It was pure Clay. We laughed about it when saw each other again in Binghamton later that summer.

Clay loved his family; he always spoke proudly about his wife and three daughters. I’ll miss him. RIP Lefty.

No Stopping No-Hitters

Last week I asked if any of you had ever seen a no-hitter in person. I got some great answers, including one from my own father who was with his grandfather at Memorial Stadium in Baltimore on September 20, 1958, when Hoyt Wilhelm no-hit the Yankees. It looks witnessing a no-no skips a generation in my family.

Without a doubt, though, the most timely feedback came from a WTP subscriber who was at Globe Life Field on Wednesday when Corey Kluber accomplished the feat against the Rangers.

So far this season, the Rangers, Indians, and Mariners have each been no-hit twice. Any takers on a third time?

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