MLB milestones to watch in 2026: Who will join 400-home run club? Can Dodgers or Tarik Skubal three-peat?

The 2026 Major League Baseball season will soon be upon us. This, of course, means that success or failure at the team level — the current standings and pennant races and all of that — takes primary focus. Unfurling at the same time are those very much related individual performances. Yes, the MVP and Cy Young derbies get most of that bandwidth, but let’s not forget about veteran performers closing in on milestones.

Each MLB season brings a new crop of aspiring history-makers and the 2026 campaign figures to be no exception. So let’s have a look at the most notable of these benchmarks that might be reached at some point during this season. In ascending and thrilling numerical order!

The three-peat: Los Angeles Dodgers

It’s a tall order to win back-to-back titles in a sport like baseball. When the Dodgers did that in 2025, they were the first to repeat as World Series champions since the 1999-2000 New York Yankees. As you would expect, the three-peat, or winning three straight World Series titles, is even rarer. Throughout all of MLB history, just four teams have managed to win three or more World Series in a row: 

As you may have surmised from the above, the 2026 Dodgers have the chance to be the first National League ever to pull off the three-peat. They’re certainly well positioned to do it, what with their rotation depth, superstar core, and the offseason additions of outfielder Kyle Tucker and closer Edwin Díaz. You should always take the field over any one team in baseball, but the Dodgers this season have a real shot at joining such exclusive company. 

Three straight Cy Youngs: Tarik Skubal

The Tigers’ ace of aces is in his walk year, and what better way to position oneself for free agency than by winning a third straight Cy Young award? Skubal was the unanimous winner in the American League in 2024, and last season he took 26 of 30 first-place votes. His stuff, recent health history and durability, and his underlying dominance all suggest that Skubal will again be operating at peak in 2026. If he does win the hardware this season, then he’ll be the first AL pitcher ever to win three in a row. The only other pitchers to win three or more Cy Youngs consecutively are Greg Maddux of the Braves (1992-95) and Randy Johnson of the Diamondbacks (1999-2002).

As a bonus, Skubal in 2026 can also become just the sixth pitcher to lead his league in ERA for three or more seasons in a row. The others to pull it off are Lefty Grove, Sandy Koufax, Roger Clemens, Maddux, and Clayton Kershaw.

Three straight 30/30 seasons: José Ramírez

Ramírez is one of the most well-rounded and ruthlessly consistent players of his era. Speaking of which, Ramírez has in each of the last two seasons topped 30 home runs and 30 stolen bases. To be more specific, he’s topped 30 homers and 40 steals in each of the last two seasons, but 30-40 doesn’t have the same pleasing symmetry as 30-30. As long as we’re piling on, let’s also note that J-Ram eclipsed 30 doubles, as well, in 2024 and 2025. Anyhow, only one player — Barry Bonds from 1995-97 — has managed three straight 30-30 seasons.

Four straight MVPs: Shohei Ohtani

The peerless Ohtani last season claimed his third straight MVP award as he clouted a career-high 55 home runs and also pitched like an ace across 14 starts (1.90 FIP!) as he returned to the mound after recovering from a Tommy John hybrid procedure. He won the MVP in 2024 thanks to the first 50-50 season in MLB history, and in 2023 he claimed top honors as a member of the Angels. Only one other player, the aforementioned Barry Bonds, has won at least three straight MVP awards. Indeed, Bonds won four straight from 2001-04. A year after becoming just the second player ever to win three consecutive MVPs, Ohtani can become the second to win four in a row. Since Ohtani going into his age-31 campaign remains at peak, he’ll be the favorite in most quarters to win it yet again. At present, he’s won four MVPs in eight MLB seasons.

Top five all-time in strikeouts: Justin Verlander

The three-time Cy Young winner and active leader wins, Verlander is back in Detroit where it all started. The Tigers are hoping the franchise legend will help stabilize the back of the rotation after Reese Olson underwent season-ending shoulder surgery, and along the way he could make some history. Verlander enters the 2026 season with 3,553 strikeouts. That lofty tally makes him the active leader in the category and puts him in eighth place on the all-time list. Here’s the current top 10:

Verlander, 43, is coming off a 2025 season for the Giants in which he struck out 137 batters in 152 innings. He needs 148 strikeouts to tie Blyleven for fifth place on that list above, but Verlander hasn’t reached that total in a season since 2022, when he won his most recent Cy. So consider him unlikely to crack the top five in 2026. Still, he’s close enough for this possibility to merit mention. If Verlander is able to shoulder a heavier innings load than expected in 2026 or if he ramps up his strikeout rate, then it could happen. 

Top 10 all-time in strikeouts: Max Scherzer

Just missing that top 10 above is Mr. Scherzer with 3,489. Back with the Blue Jays, he needs just 11 strikeouts this season to become the 11th pitcher ever to reach 3,500. He needs a mere 20 strikeouts to tie Walter Johnson for 10th place on the all-time strikeouts ledger. Scherzer, now 41, hasn’t been the picture of health and durability over the last two seasons, so vaulting high up the list seems unlikely. Passing Don Sutton for seventh place, however, is a realistic possibility.

As a bonus, Scherzer is also 26 starts away from reaching 500 games started for his career. He’d be the 51st moundsman ever to reach that milestone. That, though, would require him to be mostly durable and stick in the rotation for the entire season.

400 home runs: Goldschmidt, Machado, Judge, Freeman, Harper

Yes, a number of venerable sluggers have shots in 2026 at joining the 400-homer club, which at present has 59 members (including, most recently, Mike Trout). None of the above is an immediate threat, but the second half of the season could see the ranks of the club grow by one or more. Specifically, Goldschmidt needs 28 home runs for 400, Machado needs 31, Judge needs 32, Freeman needs 33, and Harper needs 37. Given ages and performance trends, Judge is the strongest bet, followed by, perhaps, Machado. Normally we wouldn’t name check a guy who needs 60 homers to reach 400, but we’ll make an exception for Kyle Schwarber since he hit 56 last season.

500 saves: Kenley Jansen

At this writing, just two closers — both Hall of Famers — have at least 500 career saves. The peerless Mariano Rivera leads all comers with 652 and Trevor Hoffman is second with 601. Third is Lee Smith with 478, and then comes Jansen at 476. High-level mathematics will tell you that Jansen needs 24 more saves to become the third closer to get to 500. He’s in line to get save opportunities for the Tigers, likely contenders, so barring major injury or swift age-related decline, Jansen should get there. He’s cleared 24 saves in every season in which he’s been a full-time closer, save for the heavily abbreviated 2020 campaign. Jansen’s also 67 appearances away from becoming the 17th hurler ever to log 1,000 or more games pitched. He most recently topped 67 appearances in a season in 2021, and he’s cleared that bar five times in his career.

2,500 hits: Freddie Freeman and Jose Altuve

Before the march to the much more ballyhooed 3,000 comes the precursory march to 2,500. Freeman and Altuve are in need of, respectively, 69 and 112 hits to reach 2,500. If these stalwart batsmen do so, they’ll become the 102nd and 103rd hitters to reach the benchmark. Barring serious injury, Freeman and Altuve will both get it done in 2026. With 53 more doubles/triples/homers, Freeman will also become the 40th player ever to amass at least 1,000 extra-base hits. Last season, Freeman had 65 extra-base knocks.