8 players who could be candidates for extensions

April 14th, 2019

Since last season's World Series ended, Major League clubs have handed out contract extensions to 32 players worth more than $2.25 billion combined, a new trend that will keep some of the game’s biggest stars in their current uniforms for years to come.

A few weeks ago, we looked at 10 stars who were candidates for their own extensions, nine of whom were scheduled to become free agents between 2019-21 (from that list, and have already signed new deals). Today, we look at some players that haven’t even reached arbitration yet and are worthy of locking up for the long-term.

A little more than a week ago, the Braves locked up for the next eight years at $100 million. Then on Thursday, the Braves struck again, signing to a seven-year extension worth $35 million, including a pair of option years that could keep him with the club through 2027.

Which other young stars might be next to join the extension craze? Here are eight to consider, listed in order of service time accrued heading into the 2019 season, starting with the most.

Andrew Benintendi, LF, Red Sox: The Red Sox have already been busy doling out extensions during the past month, signing Sale (five years, $145 million) and Xander Bogaerts (six years, $120 million with one option year). Mookie Betts appears destined to become a free agent in two years, while J.D. Martinez may opt out of the final three years and $62.5 million of his deal at the end of this season.

Benintendi won’t be arbitration-eligible until next offseason and isn’t slated to become a free agent until the end of the 2023 season, but given the uncertainty of Betts’ situation beyond 2020 -- not to mention Boston’s apparent desire to keep the core of this current team together long-term -- why not try locking up Benintendi now to eat up his arbitration years along with two or three years of free agency? He’s 24 (he’ll turn 25 in July) and has already established himself as an all-around threat both at the plate and in the field.

Aaron Judge, RF, Yankees: Giancarlo Stanton was two years away from free agency when he signed his 13-year, $325 million contract in November 2014, a deal that accounted for his final two years of arbitration and a whopping 11 free-agent seasons. Stanton had averaged 33 homers, 85 RBIs and 134 games per year in his first four full seasons with the Marlins, with a second-place finish in the National League Most Valuable Player Award race in 2014, his age-24 season. Judge hasn’t played as long as his now-teammate Stanton had when he inked his record-breaking extension, though he’s older than Stanton was at the time of his deal. Judge turns 27 on April 26 and won’t be a free agent until the end of his age-30 season, a tough age for players on the open market in recent years.

Judge averaged 40 homers and 90 RBIs in his first two full seasons, one of which saw him finish as the American League MVP runner-up. Those numbers would have been even more inflated had he not missed 50 games with a wrist injury in 2019, but Judge’s value to the Yankees -- both on and off the field -- is obvious. The Yankees have traditionally let their players go year-to-year, knowing they have the financial wherewithal to re-sign them as free agents, but the contract extensions they gave to Aaron Hicks and Luis Severino this past offseason could be a sign of a new philosophy.

Kyle Freeland, LHP, Rockies: Freeland had a breakout performance in his age-25 season last year, finishing fourth in the NL Cy Young Award race after posting a 2.85 ERA, earning 17 wins and topping the 200-inning mark in his sophomore season. He’s eligible for arbitration for the first time after this season, and free agency following the 2023 campaign.

Blake Snell (five years, $50 million) and Rockies teammate German Marquez (five years, $43 million with one option year), who both signed recent extensions, are fairly good comps for Freeland:

Freeland: 28-18, 3.39 ERA, 358 1/3 IP, 143 ERA+
Snell: 32-20, 2.95 ERA, 399 IP, 139 ERA+
Marquez: 27-20, 4.06 ERA, 378 2/3 IP, 118 ERA+

Snell’s resume also includes the 2018 AL Cy Young Award, an achievement Freeland can’t match, though Freeland had his big year while making 15 of his 33 starts at hitter-friendly Coors Field. The model for a potential Freeland extension would likely fall between the Snell and Marquez contracts.

Adalberto Mondesi, SS, Royals: Whit Merrifield signed a four-year, $16.25 million extension with the Royals, who also have an option year on the second baseman. But Merrifield is 30 years old and wouldn’t have been eligible for free agency until he was 34, so the deal made sense for him. Mondesi -- the son of former NL Rookie of the Year and All-Star Raul Mondesi -- turns 24 this summer and will be a free agent at 29, putting him in a better spot to cash in.

Mondesi played well in a half-season last year (14 homers, 37 RBIs, 47 runs scored, 32 stolen bases and an .804 OPS in 75 games) and is off to a solid start in 2019 (.874 OPS with eight extra-base hits, including a Major League-high three triples through 10 games). The Royals built their 2015 World Series championship team on homegrown talent, so locking up Mondesi while creating cost certainty through his arbitration years -- and possibly buying out a year or two of free agency -- would seem to be a sensible move.

Rhys Hoskins, 1B, Phillies: Through his first 203 games, Hoskins hit 52 home runs with 144 RBIs and an .889 OPS, establishing himself as one of the game’s top power threats. For comparison’s sake, Alex Bregman -- who signed a five-year, $100 million extension last month -- had 27 homers, 105 RBIs and an .818 OPS through his first 204 big league games, albeit as a stellar defensive third baseman and with one more year of service time.

Bregman went on to produce an All-Star season in his third season and finished in the top 5 in MVP voting, hitting 31 homers with 103 RBIs, a league-high 51 doubles and a .926 OPS before signing his extension. But Hoskins is already off to a blazing start in 2019, cementing his status as a middle-of-the-lineup hitter at 26. The Phillies went all-in with the signing of Bryce Harper and locked in Aaron Nola for the foreseeable future, so it wouldn’t be shocking to see them take the same approach and try to sign Hoskins to an extension of his own. Hoskins is not eligible for free agency until after the 2023 season.

Juan Soto, LF, Nationals: Acuna may have 25 more days of service time than Soto, but the two outfielders figure to be linked together for their entire careers following their race for the 2018 NL Rookie of the Year Award. Soto won’t turn 21 until late October, so even as a potential Super Two with four years of arbitration eligibility, he’s on a trajectory to reach free agency entering his age-26 season -- the same situation Bryce Harper and Manny Machado found themselves in this past offseason.

The Nationals haven’t been aggressive when it comes to locking up young players, letting their stars go through the arbitration process. Nor has agent Scott Boras been one to negotiate these types of early extensions, recently telling the Los Angeles Times that Acuna’s deal was “the king of the snuff contracts,” designed to snuff out the market. That said, the idea of landing a nine-figure deal before his 21st birthday might intrigue Soto enough to press the issue.

Fernando Tatis Jr., SS, Padres and Vladimir Guerrero Jr., 3B, Blue Jays: Much like Acuna and Soto, these two are likely to be linked together for a while, so we are grouping them together here.

Handing a sizeable extension to players that haven’t proven themselves in the Majors yet is certainly a risk, but just as the White Sox took a leap of faith by giving Eloy Jimenez a six-year, $43 million deal (with two option years) before he had taken a single big league at-bat, the Padres and Blue Jays would be wise to do the same with their respective top prospects.

San Diego made a brash, bold statement by opening the season with Tatis on its Opening Day roster, potentially costing itself a year of club control in the process. Signing the talented 20-year-old shortstop to an extension (ideally with some option years) would make perfect sense, especially with Manny Machado signed for 10 years with an opt-out after 2023. The same goes for the Blue Jays and Guerrero, MLB Pipeline’s top prospect in all of baseball. Even before he suffered an injury during Spring Training, the 20-year-old infielder was likely to start the season in the Minors for service-time purposes, but like Jimenez, an extension would end the need for any such conversation and give Toronto fans something to be excited about.

One thing to consider when comparing the two: Guerrero got a $3.9 million bonus from the Blue Jays when he signed in 2015, while Tatis got $825,000 from the White Sox before being traded to the Padres. In other words, Tatis might have a little more incentive to seek long-term security given his relatively modest bonus.