SF Giants: How does Logan Webb's deal compare to other recent extensions?

The SF Giants inked Logan Webb to a five-year, $90 million extension earlier this month. How does Webb's contract compare to his peers?

The Logan Webb extension was a mild surprise early this season. While it made sense for the SF Giants to lock up their young ace, there were few rumors suggesting a deal was imminent. Nevertheless, Webb’s five-year, $90 million contract should wind up a win-win scenario for both parties involved. It is the type of low-risk, high-reward deal that is fundamental for any ball club trying to build a sustainable championship contender. It also has the added benefit of extending an olive branch to a fanbase that was frustrated by the team’s failure to sign one of the top free agents this winter.

SF Giants pitcher Logan Webb throws a pitch against the Mets. (2023) / © D. Ross Cameron-USA TODAY Sports

The Giants’ 2023 Opening Day starter was drafted by the team out of high school in Rocklin, California back in the fourth round of the 2014 MLB Draft. His stock took a steep climb up the mock draft big boards during his final high school season after he saw the velocity on his fastball jump during a game in which a plethora of scouts came to watch the opposing starting pitcher. Receiving a six-figure signing bonus, the former quarterback forewent his scholarship to Cal Poly and joined the Giants organization. Indeed, that selection and Webb’s decision to forego college have both worked out well for both teams.

The Webb extension is a win-win situation for all parties involved. Webb pushes his opportunity to reach free agency back three years, but guarantees himself significantly more money than he would have received via arbitration in the subsequent years. Now, regardless of health or on-field performance, he’s ensured himself nearly nine figures in career earnings.

Webb was shrewd to sign an extension without any team options. Even with a delayed free agency, he will only be 31 years old when his extension expires in 2029. If Webb stays healthy and near his current level of performance for this present contract, he could easily cash in again with another massive contract, possibly one eclipsing nine figures.

This is also a very fair contract based on the other recent extensions given to veteran starting pitchers. Webb falls in an interesting space. Most players either ink extensions on the cusp of free agency or very shortly after their MLB debuts. Nevertheless, over the last calendar year, extensions for starting pitchers with at least three years of service time (like Webb) have averaged roughly $77 million dollars in total guarantees alongside an $18 million average annual value. Here’s a specific look at some of those contracts and how they compared to the 27-year-old’s situation:

Miles Mikolas: three-years, $55.75 million

Mikolas had a very different career trajectory than Webb. A mid-30s veteran who did not establish himself in the majors until returning from a stint in Japan, Mikolas was set to hit free agency next offseason before accepting a two-year, $40 million extension prior to Opening Day. During his tenure with the Cardinals, Mikolas has a 3.62 ERA in 110 starts across 657 innings pitched with a 41-45 win-loss record. Mikolas had noticeably more leverage than Webb, since he was only under contract for one more season, but shows the value for the Giants in the extension.

Hunter Greene: six-years, $53 million

Most of the pitchers on this list had less remaining team control to negotiate against than Webb, Greene is a notable exception. The former second-overall pick made his big-league debut last season and struck out 164 hitters in 125.2 innings pitched. While Greene's deal has the potential to eclipse $90 million in total value with escalators and incentives, the Reds have a club option.

Pablo Lopez: four-years, $73.5 million

Traded from Miami to Minnesota in a one-for-one deal for Luis Arraez, Lopez signed an extension with Minnesota during spring training. The 26-year-old veteran had five years of service time from his tenure in Miami, and was under team control for two subsequent seasons. Lopez only traded two years of free agency (Webb traded three) for some guaranteed earnings and received a comparable average annual value. However, Lopez has struggled to stay healthy throughout his career, which kept him from matching Webb's total guarantees.

Joe Musgrove: five-years, $100 million

San Diego native Joe Musgrove signed an extension with his hometown team that likely passed up significant earnings last season. Musgrove has proved to be a bonafide ace since joining the Padres in 2021, and agreed to a five-year, $100 million extension just a couple months before he was slated to reach the open market. While Webb was in a similar potential "hometown discount" situation, he was able to nearly match Musgrove's deal despite notably more team control.

Yu Darvish: six-years, $108 million

Easily the oldest recent extension recipient, Yu Darvish signed a 5 year, $90 million dollar extension with the Padres at age 36 in February. Darvish was going to be a free agent at the end of this season. He finished eighth in last year's National League Cy Young Award voting (Webb finished 11th).

The Giants get to extend a starting pitcher that will occupy one of the top spots in the rotation that was drafted and developed by the organization. Webb being from the Greater Sacramento area adds another facet to this feel-good draft-and-develop story. This deal should also have no impact on the Giants' ability to spend in free agency or with other extensions. Webb’s deal carries an average annual value worth less than 8% of the current luxury tax line. When comparing his extension to the ones signed by other veterans, Webb matched the average annual values (AAV) despite having far less proximity to free agency to leverage.

The SF Giants front office finally locked up the team’s ace early in the 2023 season, signing Logan Webb to a five-year extension. The deal makes obvious sense for the team and should also give Webb another chance to land a massive contract in his early thirties if he remains one of the best pitchers in MLB.