Whose Contract Extensions Should Teams Tackle with Urgency?

If you look at teams with long-term stability, you’ll tend to find teams who have managed to get a lot of their best talent inked to contract extensions. When it comes to team construction, that certainty makes resolving other questions about the team a simpler matter and reduces the risk of a nasty surprise when your rival decides to spend the GDP of a small country on one of your best players in baseball. Making sure your core is locked up has been trickier since the mid-1970s, as it shockingly turned out that when you allow players to choose their employer, they may choose to find new employment! Teams as widely varying as John Hart’s 1990s Cleveland teams to today’s Braves employed these strategies as foundation of their continued success.

This year has already seen a number of key players signing long-term contracts that guarantee them healthy amounts of guaranteed cash: Corbin Carroll, Andrés Giménez, Keibert Ruiz, Miles Mikolas, Jake Cronenworth, Logan Webb, Ian Happ, Pablo López, Bryan Reynolds, and Hunter Greene have all signed deals within the last two months. Signing players now is usually better than waiting to later, so here are my eight players who teams should most urgently attempt to sign to long-term deals. For each player, I’ve included the current ZiPS-projected contract.

First off, let me address two players who you might expect to see here but who are not: Shohei Ohtani and Juan Soto. Ohtani looks like such a mega-blockbuster free agent that I’m not sure the Angels can realistically keep him from hitting the open market, and in any case, the projection would just be “all the currency that exists or ever will exist.” As for Soto, as much as it suprises me that I’m saying this, there’s enough of a question around where his ability level is right now that I think a meeting of the minds may be very difficult. The fact is that he’s a .234/.398/.437 hitter over the last calendar year, and with extremely limited defensive value, I’d actually be a little squeamish about offering him the 14-year, $440 million extension he turned down from the Nats.

Adley Rutschman, Baltimore Orioles – Six years, $141 million

Rutschman is the first player for whom the MLBPA’s new service time rule, giving the top two Rookie of the Year candidates a full year of service time, comes into play (Julio Rodríguez, Spencer Strider, and Michael Harris II all signed extensions). This means the O’s get four more years of Rutschman’s services rather than five, and a little more urgency is in order. Baltimore probably should have been in full-court press to sign him to an extension a year ago, but with Rutschman now established in the majors as one of the elite catchers and that much closer to arbitration, he’s going to be more expensive than he would be in 2022.

Ownership seems to have little interest in investing much in the team these days, but even the Rays could find the funds to guarantee Wander Franco $182 million. Baltimore never really made a serious push to extend Manny Machado pre-arbitration when it still could; it would be humiliating if the two best position players to come up through the system since Cal Ripken Jr. made the Hall of Fame without an Oriole bird on their cap on their plaques.

Julio Urías, Los Angeles Dodgers – Eight years, $186 million

There’s a good chance the Dodgers simply wait until Urías hits free agency to talk extension, but that’s an extremely risky strategy. In an alternate universe in which Walker Buehler wasn’t out with Tommy John surgery and Clayton Kershaw wasn’t seemingly on the precipice of retirement every winter, this might be a viable strategy, but Urías has been their stable rock in an increasingly turbulent pitching staff. Even though the Dodgers have a knack for finding pitchers out of nowhere, there are limits, and it’s not as if they’re woefully short on cash. And the team’s extreme care with Urías as a young player has finally paid off: he is sixth in baseball in innings pitched since the start of 2021 and has a lower ERA than any of the five pitchers ranking above him.

Jordan Montgomery, St. Louis Cardinals – Five years, $91 million

Assuming it’s not near bedtime when you read this, close your eyes and think of the Cardinals’ rotation this year. Now imagine it without Montgomery, apparently the only starting pitcher on the team who is able to get major league batters out without Yadier Molina catching. Montgomery isn’t likely to get ace money; he’s more Sain than Spahn, but certainly better than praying for rain. And while I may be the biggest fan of Matthew Liberatore remaining, even in the best-case scenario, the Cardinals likely need to replace 300 innings worth of Adam Wainwright and Jack Flaherty this winter, and Liberatore can hardly cover that. Give Cards fans something to be happy about now and, for heaven’s sake, don’t move Monty to another position a month into his extension.

Aaron Nola, Philadelphia Phillies – Six years, $103 million

Getting Nola to sign an extension has a number of stumbling blocks. First off, both he and the Phillies already called off their extension talks, and this projection isn’t drastically different from the offer that he already turned down. The other complication is that Nola is off to a weak start, and it’s more than just bad luck; ZiPS has chopped off about $13 million from this projection since the start of the year. All that being said, it’s still in the interest of the Phillies to get this done. Andrew Painter is a great prospect, but even if he’s healthy, it’s a lot to ask him to replace Nola’s production instantly. And instantly is what the Phillies need; their core is aging, and they’re at risk of 2022’s World Series appearance being the easy high-water market for this generation. This is one place the team could justifiably overpay what a projection suggests.

Marcus Stroman, Chicago Cubs – Four years, $98 million

Stroman is technically still signed for 2024, as he can opt out of his final salary of $21 million ($23 million if he makes it to 160 innings this year). While I agree with ZiPS that he won’t get a big boost on a per-year basis — he’s more Montgomery than Urías or Ohtani — he can certainly get better long-term security than a one-year deal if he hits the market. As the Cubs work on building the core of their next top-tier contender, Stroman should play the solid veteran no. 2 starter that Jon Lester played so well in the mid-2010s.

Shane Bieber, Cleveland Guardians – Five years, $95 million

José Ramírez and Andrés Giménez are both locked up to extensions, and Steven Kwan is still a long way away from free agency, leaving Bieber as the most important Guardian not inked to a long-term deal. He’s not quite the pitcher he was pre-COVID, functioning as more of the crafty veteran lefty trope these days (despite being right-handed) with his fastball no longer a swing-and-miss pitch. But the combination of his cutter, slider, and knuckle-curve keep him at the top of the rotation, and Cleveland was confident enough in his health to make him one of the increasingly rare 200-inning pitchers last year. A free agent after 2024, his loss would leave a massive crater in the rotation, even in a weak division like the AL Central. This projection, like that of Nola, also reflects that he’s off to a rather poor start in 2023.

Willy Adames, Milwaukee Brewers – Seven years, $219 million

A lot of shortstops have hit free agency the last few years, but after the flood of high-quality players available at the position in free agency the last two winters, the spigot has been abruptly turned off. Don’t believe me? Here are the top 20 shortstops over the next five years in ZiPS WAR and the year which they can first hit the open market.

In other words, if the projections are correct, there’s no better shortstop available in free agency until 2028 than Adames. Bo Bichette projects at nearly the same WAR, but it still leaves a much less robust shortstop market than we’ve seen recently. Adames is a big part of Milwaukee’s offense, and the team can ill-afford to lose his power at a key defensive position.

Vinnie Pasquantino, Kansas City Royals – Seven years, $54 million

Pasquantino is not a superstar, but the Italian Breakfast has turned out to be the most developed of the team’s hitting prospects. Whit Merrifield is gone, and Salvador Perez is entering his mid-30s, and as the Royals continue to shift away from the last of their World Series winning roster, Pasquantino should spend the next five or six years hitting in the middle of the order. Locking him up now keeps him at a Royals-friendly price throughout his likely prime years.