What Are Some Notable Milestones Within Reach for Active MLB Legends?

With every passing day in Major League Baseball, new stars are born that will leave future generations in awe. And while baseball is more youth-oriented than ever before, we cannot forget to celebrate the legends who paved the way. Not to say that the names about to be listed are old geezers by any means, but it’s hard to have milestones to achieve without a storied and long career before them. This article will display which celebrated milestones are achievable for notable active players in the 2025 MLB season, and whether they can be attained by the time October comes around.

From what aims to be a complete career with the Dodgers, Clayton Kershaw is a slam-dunk Hall of Famer. He has a genuine case to be heralded as the best Dodgers pitcher of all time in a crop that is loaded with icons and legends. Frankly, it is easy to see why when you take a look at his accomplishments in a Dodgers uniform. Nine top-10 finishes in Cy Young voting, including three trophies taken home for good measure. Three top-10 finishes in MVP voting, including a victory of his own. A career ERA of 2.51 and WHIP of 1.013 in 18 seasons. And even despite his postseason struggles, Kershaw has contributed to the Dodgers’ two most recent World Series championships in 2020 and 2024.

There are few milestones that Kershaw has yet to reach, but one that is incredibly close is 3,000 strikeouts. After his most recent start against the Rockies, Clayton Kershaw has put himself just three strikeouts away from vaulting himself into that exclusive club. Kershaw will get his chance next Tuesday against the White Sox, a team that he has a career 2.90 ERA against but only 31 strikeouts. With the home field advantage in Dodger Stadium, next Tuesday at 10:10 pm EDT should be appointment viewing for any Dodger fan.

Some are under the belief that until some guy named Shohei Ohtani showed up, Mike Trout was the best pure hitter in baseball. He had a solid argument for the best five-tool offensive threat to play the game. With 9 20+ HR seasons, 3 100+ RBI seasons, and 11 seasons with a .280 average or above, it’s a shock that he has not won more than his 3 MVPs. He has a chance to add to an already storied legacy, being only ten HRs away from 400 and 17 RBI away from 1,000 for his career.

Trout has not been the same after his recent injury-riddled seasons. However, he has still proven to be a capable offensive threat in 2025, and, if he can stay healthy, 400 HRs should be easily within his grasp by October. If Trout continues at his current pace, he should be hitting his 30th HR of the 2025 season around September, so expect the watch for number 400 to commence around late July or early August.

The Pirates are mired in yet another year of painful mediocrity. However, watching Paul Skenes develop and dominate opposing lineups has not been the only treat for the Pirates faithful. A Pirates legend through and through, Andrew McCutchen’s career has been one of triumph in Pittsburgh, where he took home an MVP in 2013 and was top-five in MVP voting every year between 2012-2015. His level of play post-Pittsburgh has tailed off, but he has still put up an illustrious career offensively. 327 HRs, 1,123 RBI, 220 SBs, and a career .827 OPS; McCutchen has done enough in his career to at least be in Hall of Fame discussions.

One more milestone that could help McCutchen’s case would be reaching 50 career WAR. It would be a nice final bow to a career that is soon coming to a close. However, as tantalizingly close as he is to reaching it, the state of the Pirates in 2025 and McCutchen’s deflated production at age 38 make it a coin toss if he can get there in 2025. Considering he has primarily operated as a DH, there is not much hope for any defensive WAR. His only hope would come from offensive production. It is not impossible, but would require a stretch at the plate that many doubt Cutch still has left in him. In any case, if Pirates fans have already abandoned ship for the 2025 season, cheering for McCutchen should help keep them steady until the offseason.

Jose Ramirez has been one of the most underrated players in Major League Baseball during his career. With every previous player mentioned in this article, a breakdown of the awards they won throughout their career follows. Unfortunately, J-Ram has never taken home an MVP award. The 32-year-old has come close, finishing in the top 10 in voting seven times, including a runner-up in 2020 and back-to-back top-three finishes in 2017 and 2018. Add that with a career 268 HRs, 902 RBI, .281 average, and .858 OPS, and you have yourself an unheralded Hall-of-Fame caliber player.

What separates Ramirez from his other counterparts at third base is his unreal speed. He has nearly as many stolen bases as he does home runs, which is incredible for someone at the hot corner. Granted, claiming that 300 stolen bases is in the realm of possibilities in the 2025 season for Ramirez is bold. However, in the current age of larger bases and limited pickoff attempts, paired with Ramirez stealing a career-high 41 bases last season, anything is possible. Ramirez has proven time and time again that he is unpredictable. Yes, he is unlikely to reach 300 swiped bags in 2025. But it will only be a matter of time before he reaches that milestone and further adds to his Hall of Fame case.

Chris Sale needs no introduction. With eight appearances within the top 10 of Cy Young Award voting, a career 3.02 ERA, 1.049 WHIP, 2,528 strikeouts, and 55.8 WAR accrued as a pitcher, his resume speaks for itself. Before last season, the baseball world thought that Sale was merely trying to cling to the twilight of his career in Atlanta. So he proved all the doubters wrong and is currently undergoing a renaissance seldom seen in modern baseball. Sale captured his first-ever Cy Young award in 2024. If the Braves had gotten off to a better start in 2025, he would be held in contention for this year’s award as well.

It’s the bizarre season from the usual powerhouse Atlanta Braves that feels like the only thing in the way of Chris Sale and reaching 150 career wins. While wins are not held in anywhere near as high regard as they were 30 years ago, garnering 150 of them is still a neat feather in the cap of any pitcher. Sale, who is trying to put whatever final touches he can on his Hall of Fame case, will take any wins he can get. His next seven starts are projected against the following opponents in order: Angels, Orioles, Cardinals, Giants, Rangers, Reds, and Marlins. None of these teams is considered an offensive powerhouse. A vintage Sale stretch of dominance could propel him to 150 wins in no time. However, that would also require a sustained level of success from the Braves offense rarely seen in 2025. Regardless, Sale’s career renaissance in Atlanta makes this milestone realistically achievable, and a similar level of production through next season will easily vault Chris into the 150-win club.

These legends chasing these milestones will be fun races to watch, no matter what team you cheer for. Each of these players looks to continue to etch their name in the Baseball Hall of Fame and solidify their legacy to future players and fans alike.