With the Atlanta Braves on the verge of saying good-bye to Max Fried via free agency, we take a look at the largest guaranteed money contracts awarded to starting pitchers in the history of Major League Baseball. We also evaluate whether or not they were worth the price with a simple thumbs up or a poop emoji at the end. That way, you don’t have to actually read anything. We are all about user experience here. Now, click on one of our ads!

This list doesn’t include contracts like Gerrit Cole’s or Yoshinobu Yamamoto’s $325 million. This list focuses on contracts that played our for us to evaluate.

Let’s take a look at the largest starting pitcher contracts every signed and try and find the answer to the age old question: Are huge free agent contracts worth it in MLB? Do these huge-money, long-term deals get a thumbs up or a thumb shoved into a tightly coiled pile? Read on to find out!

Table of Contents

1. Stephen Strasburg
2. David Price
3. Clayton Kershaw
4. Max Scherzer
5. Zack Greinke
6. Justin Verlander
7. Felix Hernandez
8. Stephen Strasburg
9. Masahiro Tanaka
10. Jon Lester
11. Conclusion – Are Long-Term, Big-Money Free-Agent Contracts Worth It?

Largest MLB SP Contract #1: Stephen Strasburg, $245,000,000 (2020-26) 💩

Strasburg pitched 31.1 innings of this contract. He had a 6.89 ERA in eight starts before retiring in April of 2024. He was a dominant pitcher when healthy, but Strasburg suffered through thoracic outlet syndrome which resulted in him having a rib and two muscles in his neck surgically removed. The Nationals had to reach a settlement with Strasburg to get him to retire and get his contract off the books. 💩

Largest MLB SP Contract #2: David Price, $217,000,000 (2016-2022) 💩

David Price played six of the seven years of his deal. He opted out of the 2020 COVID-season. Price finished the seven seasons of his deal with a 1.23 WHIP and a 3.78 ERA. After signing one of the largest starting pitcher deals in the history of baseball, Price posted a 3.99 ERA for Boston. However, he did pitch 230 innings to lead the league. Price only made 11 starts the next season and posted a 3.38 ERA. He was solid in 2018 with 30 starts and a 3.58 ERA, winning a World Series that season. He wrapped the 2020 Covid season with two 4.00+ ERA seasons, posting a 4.28 ERA in 2019 and a 4.03 ERA in 2021. Price was traded to the Dodgers in 2021 in the Mookie Betts deal. The Red Sox had to eat $96 million of his deal to get the Dodgers to take him. Price was moved to the bullpen and pitched in just 40.1 innings in his final season in 2022 at age 36. 💩

Largest MLB SP Contract #3: Clayton Kershaw, $215,000,000 (2014-20) 👍

Over the course of this contract, Clayton Kershaw went 98-30 with a 2.26 ERA while making 172 starts for the Dodgers. Kershaw averaged 25 starts per season. When he was on the mound, Kershaw gave the Dodgers exactly what they paid for in this deal. He was an elite pitcher with 10.3 strikeouts per nine, 0.91 WHIP, and just 1.5 walks per nine. Kershaw’s ERA was 72% better than league average during this contract. 👍

Largest MLB SP Contract #4: Max Scherzer, $210,000,000 (2015-21) 👍

Max Scherzer posted a 2.75 ERA over the course of this deal while making 29 starts per season. He went 99-47 with a 0.95 WHIP, 2.0 BB9, and a stunning 11.8 SO9. His 155 ERA+ puts him in rare air over the course of this deal. 👍

Largest MLB SP Contract #5: Zack Greinke, $206,500,000 (2016-21) 💩

Baseball’s favorite weirdo posted a 3.55 ERA during his time with the Diamondbacks and Astros on this deal. He made 28 starts per year and went 77-39. His first season with Arizona didn’t go as planned for Greinke as he posted a 4.37 ERA over 158.2 innings pitched. He was great during the next three years, posting a 3.11 ERA between 2017-2019. In the final two years of this deal, Greinke posted a 4.12 ERA and made just 34 starts over the final two years. Greinke finished three of the six seasons of this massive deal with an ERA over 4.00. That’s not what you pay such a huge percent of your budget for. Greinke was a very good pitcher during this time but I’m calling this one a turd of a contract. 💩

Largest MLB SP Contract #6: Justin Verlander, $180,000,000 (2013-19) 👍

Verlander won the MVP in 2011 and finished eighth in MVP voting in 2012. He was rewarded with a massive $180,000,000 contract in 2013. Verlander exceeded 200 innings in six of the seven years of this deal. He led the league in wins in the final season of the deal for the Astros, posting 21 wins with a 2.58 ERA at age 36. The old man also led the league in innings pitched that year. This was not a case of over-paying for prime years and eating the contract in the later years. Verlander posted a 130 ERA+. He had one rough season in 2014 with a 4.54 ERA, but other than that, he earned that money. 👍

Largest MLB SP Contract #7: Felix Hernandez, $175,000,000 (2013-19) 💩

This contract represents the risk when doling out so much money over long periods of time. Sure, it started great with King Felix making three-straight All-Star games. Hernandez’s ERA started sliding in the second year of the deal (2014) and it continued sliding all the way through the rest of the contract.

Felix Hernandez ERA 2013-2019

• 2013: 3.04 ERA
• 2014: 2.14 ERA
• 2015: 3.53 ERA
• 2016: 3.82 ERA
• 2017: 4.36 ERA 💩
• 2018: 5.55 ERA 💩
• 2019: 6.40 ERA 💩

Hernandez was an amazing pitcher over the course of his 15-year career, but this is not the type of production you hope for when you sign a guy to seven-years and some of the most guaranteed money in the history of the game. This is another example of paying for past production once it’s in the past. 💩

Largest MLB SP Contract #8: Stephen Strasburg, $175,000,000 (2017-23) 💩

We already discussed Strasburg earlier. He was in the midst of this contract when he had the a Postseason for the history books. Strasburg still only managed 15 starts during the course of this deal. He was really good the first three years, prior to signing the extensions. But even if he didn’t sign the extension, the injuries wiped out the entire back half of this contract. I think Nationals’ fans will probably tell you it was worth it because they won a World Series with a star player that was with their team his whole career. Just based on the value of the deal, and as Atlanta Braves fans, we give it a thumbs down. 💩

Largest MLB SP Contract #T-9: Masahiro Tanaka, $155,000,000 (2014-20) 💩

Masahiro Tanake came over from Japan with a ton of hype. I remember making it appointment-viewing television to watch his first Spring Training start. Tanaka posted a 2.77 ERA in his first season over 20 starts. He averaged just 25 starts per season and posted a 3.74 ERA over his seven-year career. Again, Tanaka was a really good pitcher but his ERA was only 14% better than the league average over the course of this contract. He never hit the 200-inning mark and averaged 150.6 innings per year. 💩

Largest MLB SP Contract #T-9: Jon Lester, $155,000,000 (2015-20) 💩

Lester had three really good seasons during thsi contract and three seasons with an ERA above 4.00. A total ERA+ of 115 with a 1.25 WHIP and a 3.64 ERA is alright, but probably not what you hope for when awarding one of the largest guaranteed contracts to a starting pitcher in history. 💩

Conclusion – Are Long-Term, Big-Money Free-Agent Contracts Worth It?

💩: 7

👍: 3

Based on our calculations, 70% of the top 10 contracts (excluding Cole’s, which is incomplete) have been turds.

Are these long-term contracts worth the risk? The answer is a definitive maybe. Even many of the turd contracts had multiple seasons of excellence over the duration of the deal. Reliable starting pitching over a long period of time carries a lot of value in the Major Leagues. Do you have to commit huge portions of a team’s budget to one guy for oftentimes too many years to get it? No.

If the team has the resources and is okay with paying above market value and potentially eating the bad years of a contract, then it isn’t so risky. If the only way the contract works out is elite production every single year of the deal, it’s probably not worth the risk.

Alex Anthopoulos and the Braves avoid these types of deals like the plague. They often turn into situations where you pay old guys for the production of their youth while they whither away.

Note: We’ve set the official talkintomahawk.com record for most poop emojis in one article. Congratulations to you for being a part of history.

Also Read:

• 2025 MLB Free Agents
• Why Braves Won’t Re-Sign Max Fried
• 8 Braves Free Agents in 2025