What Might an Extension Look Like with Brandon Woodruff?

There will be many interesting decisions to be made this offseason. It is very possible that the front office may have more conversations internally about Brandon Woodruff than anyone else. He is under team control for the next two seasons and has earned significant raises. They could just go year to year. They should at least work with Woodruff’s representatives about a long-term deal, but if he is completely against that idea and looking to become a free agent, the Brewers owe it to themselves and the fans to consider trading him at peak value. 

But in this article, we are discussing the idea of a long-term contract extension with Woodruff. There are, of course, several factors that go into the decision to retain a player for an extended period of time. 

The first factor, obviously, is performance. Performance can be looked at in two ways. First, consider his statistics and track record. Well, Woodruff has been an All-Star twice in the past three seasons with All-Star games (there was no game in 2020). His ERA+ since 2019 have been 123, 149, 161, and 129. He received Cy Young votes in 2021 when he went just 9-10 but had an ERA of 2.56 and a WHIP of 0.97. In an average year, he is worth more than 3 fWAR. Based on that, he has been worth $108.7 million over the past four years. 

The performance also speaks to his stuff. Has he lost anything, velocity, spin, etc.? Well, Woodruff’s average fastball in 2019 was 96.3 mph. In 2022, it was 96.2 mph. He’s got a four-pitch mix. He’s got good control and command. 

So there are the reasons that the Brewers should absolutely want to lock up such a talented arm. In addition, anyone who has watched the playoffs knows that for a team to make a legitimate run toward a World Series title, they have to have at least two, and preferably three or four top starting pitchers. 

A big concern, especially with pitchers, has to be an injury. While past health doesn’t necessarily mean a pitcher will remain healthy, the track record is really all teams have to go by (although, they get access to his medicals before such expenditures are made). 

Brandon Woodruff has been on the Injured List three times. In 2019, he had an Oblique injury. In September of 2021, he was out with an illness. In May, he missed time with a sprained ankle. At that time, he confirmed that he had been diagnosed with Raynaud’s syndrome. It is a circulatory condition that causes numbness in the extremities due to reduced blood flow. While it doesn’t appear to have any real short or long-term effects, it is something to keep in mind. 

Comparable Contracts
There have been a couple of long-term extensions for pitchers with similar success to Woodruff. Late this season, Luis Castillo signed a five-year, $108 million deal with a vesting option for 2028. Last November, the Blue Jays signed Jose Berrios to a seven-year, $131 million contract. 

Let’s start with the Berrios contract. The Puerto Rican right-hander had been acquired by Toronto from the Minnesota Twins in exchange for top prospects Austin Martin and Simeon Woods Richardson. It certainly had to be a goal of the Blue Jays’ front office to keep him beyond the 2022 season. He was able to get a seven-year deal because he was about two years younger than Woodruff at the time of the deal. 

Luis Castillo is actually about three months older than Woodruff and their service time is very similar. Castillo has twice been an All Star and put up terrific numbers in Cincinnati. He was acquired by the Mariners before the trade deadline this year and pitched very well in a pennant race and in the playoffs. Castillo has three plus-pitches and his fastball is just a bit faster than Woodruff’s, but the Brewers’ co-ace has slightly better statistics. His FanGraphs WAR has been worth $112.3 million over the past four seasons.  

There are a few things about these two agreements that the Brewers could choose to add to a Woodruff deal. For instance, if Castillo throws 180 or more innings in 2027, his $25 million contract vests. However, if he missed 130 or more days in 2025 through 2027 with a UCL injury, it becomes a $5 million team option. He has a full no-trade clause for the first three years of the deal, and if he’s traded over those final three years, he gets a $1 million bonus. Berrios has an opt-out after the 2026 season. There is a limited no-trade clause. He also has incentives in his deal based on his performance in 2025 and 2026 that could increase his 2027 and 2028 contracts by up to $5 million. 

So, let’s get to a proposal I would send to Woodruff and his agents and advisors. 

This contract is incredibly similar to Castillo’s overall. I’ve included signing bonuses for each season. It would guarantee Woodruff five years and $110 million, an average annual value of $22 million. I personally like to include a team option or two, and in this case, I have an option for a sixth season at $25 million with a $5 million buyout. So, the contract could be worth $130 million over six seasons. 

I think that deal, if it could be completed, would be a home run for the Brewers and a very fair deal for Woodruff. Maybe a home run for both?

So what do you think? Is this a contract that you would feel comfortable with the Brewers offering Brandon Woodruff? If his side is willing to negotiate from there, fantastic. If they basically scoff at the offer, then the team should reach out to other organizations to see what his trade value is. If they’re not happy with the offers, then you offer him arbitration, have him pitch in 2023 for something around $10-12 million, and try again next offseason with the same three options.  

Your turn. Share your thoughts.