Who Should Bat Leadoff This Year for the Yankees?

Who Should Bat Leadoff This Year for the Yankees?

More Frozen Early-February Thoughts by Cary Greene

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Around this time every season, in recent memory, the usual question starts to form in the minds of Bronx Bombers fans and then the ubiquitous noise surrounding who should bat leadoff for the Yankees begins. Last year, the Yankees deployed no less than 12 different players in the leadoff position in a lineup that overall, that led the league in OPS+ (118); Sluggine Percentage (.455);  Walks (639);  RBI’s (820); Home Runs (274) and  Runs (849) - while also finishing second in OBP (.332); and eighth in Stolen Bases (134) and twelfth in Hits (1371). Granted, the Yankees finished with the third most strikeouts (1463) in the league and they had a surprising lack of extra base hits, other than home runs of course.

Supporters of Michael Fishman and his staff of Yankees analytics people will argue that the roster that Yankees GM Brian Cashman has put his faith in produced the very epitome of a three outcomes baseball team. The Yankees offense last season, in a vacuum, was pretty amazing! Unfortunately, it was exposed by strong postseason pitching and the current Yankees championship drought withers on.

Very clearly, the Yankees central strategy every year is to put a batter with a high OBP at the top of the lineup, thereby giving the Yankees a high percentage chance of plating the runner with the long ball. If the Yankees leadoff hitter can get on base, the thinking is that one of the big boppers coming up behind said base runner will drive in an extra run via the home run. This strategy has proven to work great in fantasy baseball, but does it truly correlate to winning championships in MLB baseball? Unfortunately, there’s no proven link.

Therein lies the conundrum I propose to you today! Should the Yankees put a leadoff hitter with a high OBP at the top of their lineup, or, should they perch a home run hitter who also walks here and there at the top of the order? Or perhaps there’s yet a better way to skin the cat? One particular mantra I have always subscribed to is, Why be afraid to reinvent the wheel? What I mean to allude to here, is that if a team’s offense is able to score runs against elite postseason pitching, then who cares what kind of wheels the team is using? After all, they work, right!?

Therein lies the conundrum. The Yankees have kind of reinvented their own wheels right? In 1927, the Yankees swept the Pirates 4 games to none and they only hit two home runs (both by the Bambino - Babe Ruth), yet, they drove in 19 runs enroute to the massacre. You read that right! The Yankees won by driving in 19 runs and subsequently allowing only ten! Of course, it helps when you have a Wilcy Moore, Herb Pennock allowing only a combined six runs - while backed by an offense that mustered 38 hits and 13 walks on the way to victory.

You see my friends, all great offenses absolutely need run production. But the last time the Yankees were in the World Series, they produced a total of six home runs and they drove in 30. Hall of Famer Derek Jeter led off in all six games for the Yankees during the 2009 Series, he went 11-27 (.407 avg) with one walk. Jeter's OBP in that series was .427 and that, my friends, made the Yankees lineup very difficult for the Phillies pitching staff to deal with. Surprisingly, Jeter only scored five runs in the ‘09 Series, while teammate Johnny Damon, who went 6 for 22 while surpassing Jeter in runs scored, with six!

Both Jeter and Damon were superior base runners and with them both getting on base as often as they did, the Yankees table was set very nicely during the ‘09 series. Hideki “Godzilla” Matsui knocked in eight runs in the series and won the MVP award as well. So what has been missing from the Yankees since Jeter, Damon and Matsui retired? Well, I propose that the Yankees simply haven’t found top of the lineup hitters who not only get on base, but can run the bases and put genuine pressure on opposing defenses.

Wreaking havoc on the bases is an artform that appears to become lost in the true three outcome approach, where horrendous base runners like Kyle Schwarber, Brian Downing and others have been utilized by their managers to bat leadoff. The idea of putting players who are poor base runners but prodigious power hitters at the top of a lineup is simple - batting leadoff gets them more at-bats as a game wears on. Fans shouldn’t mistake the Yankees as a team that doesn’t run. Last season, the Yankees surprised a lot of people around the game with how successful they were on the bases, but alas, there still remains a very intriguing area that the 2026 Yankees might just stumble upon unintentionally

In the case of the 2025 Yankees, Trent Grisham led off in 89 games last season. While the strategy was generally successful as Grisham scored 87 runs last season while sporting a .348 OBP (4th best on the team), Grisham’s OBP was only .211 against the Blue Jays when it mattered most - during the ALDS. He only scored 3 runs in the series, as the Blue Jays pummelled the Yankees three games to one. During the regular season though, Grisham did a splendid job trotting around the bases behind all of those Aaron Judge home runs and actually, he looked great circling the diamond on all of his personal 34 dingers as well. If anyone would have suggested to me that Grisham would have clobbered the second most home runs in a single season for the darn New York Yankees, I wouldn’t have even bothered to contest such a ludicrous notion - but yes, he did precisely that!

When good leadoff men put pressure on the opposing defense and pitcher, the resulting disruption is worth its weight in gold. As Derek Jeter and Johnny Damon proved in the ‘09 series, having men on the corners can even force good pitching staffs to throw strikes to the heart of a batting order. With that cemented, here’s what I'm proposing for 2026 - if the Yankees have a player with an OBP similar to Trent Grisham, but who is a far better base runner, then the Yankees should consider not batting Grisham at the top of the order.

Second only to Aaron Judge, Grisham walked 82 times last season, so essentially what Grisham does is either hit a home run, walk or hit a single. Other than home runs, Grisham only had ten extra base hits last season - nine doubles and one triple. He hit 72 singles last season, so if we combine his walks with those singles, he was standing on first base 154 times. Grisham’s .348 OBP was fourth on the team and since he hit left-handed, he eventually settled into the leadoff spot in the Yankees lineup, so a modern day, but right-hand hitting, version of Babe Ruth could bat directly behind him. The strategy was sound and it worked. Let Grisham get on base and give Aaron Judge and company a chance to plate multiple runs when they hit a home run.

Yet, Grisham only advanced himself 3 times, via stealing second base, while also managing to get caught twice. Simply put, Grisham was a poor base runner last season, as evidenced by his minus 3.0 BsR. This made the strategy of batting Grisham first in the order kind of one dimensional. Opposing pitchers weren’t flustered or even slightly bothered when pitching to Judge when Grisham was on first base. Imagine what would happen if, instead of Grisham, a strong base runner was garnering the pitcher’s attention when Judge was at bat. It’s hard enough to deal with a good base runner, without having to also face Babe Ruth 2.0.

Here’s where things in 2026 get very interesting. If Grisham can hit home runs, singles and accumulate walks, why not bat him behind a right-hand hitting leadoff man who can not only get on base at a similar clip, but who also happens to be a terror on the base paths? A strategy like this would lengthen the Yankees lineup, as Aaron Judge would bat third. I’ve long maintained that ideally, Judge could do more damage if he hit third in the order, but in order for this to happen, the Yankees would need a true disruptor at the top of their lineup. Someone who could get on base at a near .340 clip and who could ignite the Yankees offense.

I seem to write about this every season, yet the Yankees continue to roll out the plodding DJ LeMahieu and Grisham types, instead of batting these types of players behind a disruptive leadoff hitter. Presently, we’re staring at another season of Trent Grisham and his minus three BsR at the top of the lineup. The strategy will likely work out fine, but is there a better way, if only someone could make the Yankees' adherence to three outcome strategy stop? What I’m hoping for this season is for the Yankees offense to become multi dimensional and Aaron Boone has the players, right under his nose, to accomplish just that.

Cody Bellinger did a really good job protecting Aaron Judge in the batting order last season. Not only did he hit his fair share of dingers (26), but he had 160 hits - second on the team behind Judge, who had 179. Aside from the 26 home runs, Bellinger also had 30 additional extra-base-hits. However, Bellinger doesn’t walk all that much, he only had 50 free passes last season. Another strong-suit of Bellinger’s last season was that he only grounded into eight double-plays - whereas Judge hit into 16 and Ben Rice smacked into a team leading 18. Since protecting Judge in the lineup is vitally important, it’s probably best to bat Bellinger behind Judge again this season.

Here’s why I believe the Yankees might run into a leadoff solution unlike anything they’ve experimented with yet. Enter Jose Caballero, who sublimely posted a .339 OBP last season. What jumps off the page regarding Cabby besides his electrifying 5.6 BsR is that he is a plus defender at shortstop, one who has elite range (90th percentile) and a plus arm (74th percentile). While it’s true the Yankees never intended for Caballero to be anything other than a spark plug type bench piece, the fact is that the Yankees have a glaring need for a good shortstop.

Bringing a dynamic not seen atop the Yankees lineup since Rickey Henderson back in the mid to late eighties. Henderson averaged 75 stolen bases a season when he played in the Bronx. Caballero stole 49 bases last season even though he only had 314 at-bats. If he were a full-time player, he’d likely be comparable to Henderson, minus the power of course and make no mistake, the Yankees lineup would become terrifying for opposing pitchers to deal with if Grisham was batting behind Cabby, followed by Judge, Bellinger, Stanton and Rice.

Caballero posted a 2.1 f-WAR and a 2.7 b-WAR, even though he wasn’t a full-time player. Imagine what he could do if he played more? He’s got the ability to get on base and once on, he often advances himself into scoring position. With the number of extra-base-hits that Judge, Bellinger and Rice will likely deliver, I could see Caballero leading the league in runs scored. The most questionable aspect of making Cabby a full-time player, and it’s a glaring issue, are his splits against right-handed pitching. Last season he posted a 81 wRC+ against Righties and when we contrast that against his 129 wRC+ against Lefties, Caballero is viewed as more of a platoon player than an actual starting shortstop.

What I see though, is that while Caballero didn’t do damage last season with his bat against right-handed pitching, he still was able to get on base at a .328 clip. This is an important stat, because it might mean that against right-handed starters, the Yankees might consider batting Caballero ninth. The move to make when the Yankees face right-handed starters, would be to bat Jazz Chisholm leadoff. Chisholm devoured right-handed pitching last year to the tune of  a 134 wRC+ and his OBP elevated to a .336!

You see my friends, the Yankees have a double-headed solution that could dramatically lengthen their lineup and make their offense truly terrifying to deal with. The plan I’m proposing is all about maximizing Judge, Bellinger and Rice’s run production, while simultaneously igniting the Yankees running game - opposed to having Grisham get on base and only plating him if someone hits a home run. Why not shape the lineup to be more dynamic?