The Dodgers’ acquisition of Tyler Glasnow and Manuel Margot from the Rays was contingent upon the former agreeing to a contract extension, and a new deal between Glasnow and L.A. is now in nearly complete. The Wasserman client will reportedly earn an additional $110MM over four years on top of the $25MM he’d been slated to earn. Glasnow will earn $90MM from 2025-27, and the Dodgers hold a $30MM club option on the 2028 season. If they decline their end, Glasnow has a $20MM player option (thus accounting for the $110MM in guaranteed new money). There’s no deferred money on the contract, which will be considered a five-year, $135MM deal for luxury tax purposes (equating to a $27MM per year hit).

Glasnow, 30, stands as the first notable starting pitching upgrade the Dodgers have made this offseason. His acquisition gives them a top-of-the-rotation talent to bolster the roster — albeit one who’s spent more time on the injured list than the active roster in his career. Last season’s 21 starts and 120 innings were both career-high marks for the 6’8″ right-hander, who has missed time due to Tommy John surgery, a forearm strain, an elbow strain and a significant oblique strain that kept him out for two months to begin the 2023 season.

When he’s been healthy, however, Glasnow has been nothing short of excellent. Since being traded from the Pirates, his original organization, to the Rays in the 2018 Chris Archer heist, Glasnow has worked to a 3.20 earned run average, fanned an enormous 34.1% of his opponents and coupled that with a sharp 7.8% walk rate. He’s long had better-than-average grounder rates, but last year’s 52.1% mark was a career-best. He also notched a huge 16.5% swinging-strike rate that ranked second among all pitchers with at least 100 innings.

It’s a considerably bet to make on a pitcher who’s never topped 120 innings — easily the largest contract ever for anyone with such a limited track record of durability. The four-year, $110MM in new money and effective five-year, $135MM term of the contract (for luxury tax purposes) roughly fall in line with previous extensions for high-end pitchers with injury concerns. Jacob deGrom inked a four-year, $120.5MM extension several years ago (prior to opting out and signing with the Rangers), and the contract also generally aligns with the five-year, $145MM term on Chris Sale’s Red Sox extensions. Certainly, the Dodgers will be hoping for better results from their own investment.

The rotation in Los Angeles is slated to consist of Glasnow, Walker Buehler and Bobby Miller, at present. Emmet Sheehan is likely in line for the fourth spot, while Gavin Stone, Michael Grove, Ryan Yarbrough and others battle it out for the fifth spot on the staff. Of course, L.A. is widely expected to continue adding to the starting five, with reported targets including free agents Yoshinobu Yamamoto and Lucas Giolito, in addition to trade target Dylan Cease. It stands to reason there are other pitchers in both markets currently being eyed by president of baseball operations Andrew Friedman, GM Brandon Gomes and the Dodger front office.

From a payroll perspective, the Dodgers were already squarely into luxury-tax territory, sitting at a projected $251MM, per Roster Resource. Adding an additional $2MM to account for the new tax hit on Glasnow will push them up to about $253MM, which places them $4MM shy of the second tier of penalty.

The Dodgers’ bottom-line payroll is another story entirely, thanks not only the $680MM in deferred money on Shohei Ohtani’s contract but also the $115MM in deferred money on Mookie Betts’ 12-year deal and the $57MM in deferrals on Freddie Freeman’s six-year contract. They still owe well south of $200MM in terms of actual player salary for the upcoming season, even when factoring in projected arbitration salaries. As such, there’s ample room to continue adding significant pieces to the roster, so long as the Dodgers don’t mind being taxed at increasingly steep rates. They’re a third-time luxury payor, so they’ll be taxed at 62% for any dollars spent from $257MM to $277MM, at 95% from $277MM to $297MM, and a hefty 110% for any dollars spent thereafter.

Beyond landing the biggest fish in the history of free agency and acquiring Glasnow and Margot, the Dodgers have also re-signed Jason Heyward and Joe Kelly, brought Daniel Hudson back on a minor league contract and traded lefty Victor Gonzalez to the Yankees in what’s been an active offseason so far. With clear needs in the rotation and perhaps on the bench and in the bullpen, it’s highly unlikely that Friedman, Gomes & co. will consider this their final significant deal of the winter.

Marc Topkin of the Tampa Bay Times first reported that the extension was all but finalized. ESPN’s Jeff Passan first reported the terms.