With Justin Verlander at 200 career wins and Clayton Kershaw at 150, who's more likely to hit 300?

Two future Hall of Famers took the mound on Sunday in search of a major career milestones. They both delivered.

Houston Astros ace Justin Verlander notched his 200th career win during a 9-4 win over the Athletics and give back his team sole possession of first place. Then, just 15 minutes later, the Los Angeles Dodgers’ Clayton Kershaw got career win No. 150 as his team finished up a 12-1 thumping of the Mariners.

Wins might be a heavily flawed statistic that is often influenced by several factors beyond the pitcher’s control, but they’re still meaningful to a large number of pitchers today. And big round numbers like the totals Verlander and Kershaw reached on Sunday will likely be special moments for both pitchers.

However, neither number compares to the big one: 300. Only 24 MLB pitchers have reached one of baseball’s most hallowed clubs, and only four have done so since the turn of the century.

At their current age and level of play, Kershaw and Verlander might be the two pitchers most likely to enter the club next, but there’s a fun question in there: Who’s more likely to do it?

The case for Justin Verlander hitting 300 wins

The biggest factors Verlander has going for him are all pretty significant. He’s still mowing down hitters at one of the best paces in baseball even though his velocity has dropped since his peak. His 33.5 percent strikeout rate ranks fourth in all of baseball this season, his 2.65 ERA ranks seventh and his 169.2 innings pitched rank second. Even at age 35, that’s still a bona fide ace.

But there are those dirty words: age 35. Verlander still has 100 wins to go, and he’ll have to try to reach that milestone as he hits the back end of his 30s and almost certainly into his 40s. That’s a rare accomplishment, but not impossible, and especially not for a pitcher like Verlander.

Verlander has already experienced the kind of velocity drop that has sunk so many aging pitchers and come out just fine. He also has some of the cleanest mechanics in baseball and has only hit the disabled list once in his entire career. Outside of that DL trip in 2015 due to a triceps injury, Verlander has hit 200 innings and 30 starts every season since he won Rookie of the Year in 2006.

So you have a pitcher who is getting older, but is still quite good, extraordinarily durable and very likely to play for a contender for the rest of his career. That seems like a recipe for a pitcher who can make it down the home stretch, but who knows? Pitching woes can strike anyone.

Verlander has averaged a 16-win pace per 162 games over the course of his career, something he’d have to maintain until he’s 41 to hit 300.

The case for Clayton Kershaw hitting 300 wins

Just a few years ago, Kershaw was the unquestioned favorite in baseball to reach 300 wins. He reached career win No. 100 in May 2015 at the young-ish age of 27 and after only about seven full seasons of pitching. He was the reigning MVP, a three-time Cy Young winner and had established himself as a consistent 200-inning, 30-start pitcher. Good times.

And then, well, the times weren’t so good. Kershaw had to miss a few starts in 2014 due to back issues, but he still managed to hit 198 innings. Those back issues have since returned and forced him back to the DL in 2016, 2017 and 2018 for varying lengths of time. After averaging 34 starts per season between 2010 and 2015, Kershaw is on pace for about 25 this season and an average of less than 25 between 2016 and 2018.

That is all very scary, especially for a pitcher who reached age 30 this offseason. But remember, we’re talking about Clayton Kershaw here.

Even fighting through back issues on the mound at times, Kershaw still holds by far the best ERA in MLB during that 2016-2018 span. Even if he falls off his career 2.37 ERA–which, by the way, ranks the best of any MLB starter since the deadball era–a Clayton Kershaw at, say, 80 percent of his peak is still one of the best pitchers in baseball.

Durability is much more of a concern for Kershaw than Verlander, but Kershaw has been almost unquestionably the better pitcher when the two have been on the mound in their careers. He might be 50 wins behind Verlander, but he only needs five years of a 10-win pace to reach where Verlander is right now.

If you can believe the back issues are going to be more of an annoyance than a debilitating issue for the rest of his career, it’s tough not to go with Kershaw. But that might be a hard sell, as plenty of people, not just baseball players, can vouch that back pain really doesn’t get better with age.

Basically, Kershaw reached 150 wins in his 20s (plus part of his age-30 season), and now he needs to do the same in his 30s and possibly 40s. It is a daunting proposition, and one that Kershaw himself doubted during his appearance on the Yahoo Sports MLB podcast.

Who else is in the 300-win conversation?

While Verlander and Kershaw might be the two best bets to reach 300 in baseball right now, they still only rank third and ninth respectively on the active MLB wins leaderboard.

At No. 1 is Bartolo Colon, who is holds 247 wins at the ripe old age of 45. Colon hasn’t topped 15 wins since 2013 and holds a 5.19 ERA this season, so as fun and durable a presence as he is, it’s hard to see MLB teams giving Colon enough opportunities to garner 53 more wins.

Go further down the list and you see plenty of talented, but aging pitchers. From Baseball Reference:

1. Bartolo Colon: 45 years old, 247 wins

2. CC Sabathia: 37 years old, 244 wins

3. Justin Verlander: 35 years old, 200 wins

4. Zack Greinke: 34 years old, 184 wins

5. Jon Lester: 34 years old, 172 wins

6. Felix Hernandez: 32 years old, 168 wins

7. Max Scherzer: 33 yeas old 157 wins

8. Cole Hamels: 34 years old, 155 wins

9. Clayton Kershaw: 30 years old, 150 wins

10. Ervin Santana: 35 years old, 149 wins

In the landscape of 300-win odds, there are some intriguing names on there. Scherzer could be a decent bet, as the Nationals ace is competing for a third straight Cy Young award at age 33 this season and has shown little sign of slowing down. Greinke is a good possibility to hit 200 at age 35 just like Verlander, though he’s not peaking the way Verlander is right now.

In reality, it would probably be a surprise if even one name on that list hit 300, and that’s the harsh reality of pitching these days. It doesn’t get much better with the younger generation either, as there are only three active players with at least 100 wins today and under the age of 30: Rick Porcello, Madison Bumgarner and Chris Sale. All of them still have a long way to go, with Porcello holding the highest wins total at 133.

We’re dealing with a new era of unprecedented fastball velocity and maximum-effort deliveries, and that has led to fewer innings and less durability. It’s a trade off, but it’s also what makes players who can succeed the way Kershaw and Verlander have all the more special, 300 wins or not.

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