Jazz Chisholm Jr.'s eye-popping contract demand isn't as absurd as you think

When asked what it'd take for the New York Yankees to lock him up long-term, second baseman Jazz Chisholm Jr. aimed high. "His number is $35 million for 8-to-10 seasons," NJ.com's Randy Miller wrote on Saturday. This, obviously, is a pretty wild ask: For reference, Vladimir Guerrero Jr. is making just above $35 million annually on his mammoth extension with the Toronto Blue Jays.

No, I don't expect the Yankees to give Chisholm the extension he seeks (which is why they contemplated trading him earlier this winter), and I don't expect Chisholm to receive that kind of contract in free agency. But there are a couple of things to point out before you start laughing this off entirely.

First, Chisholm prefaced his remarks by saying he was going to "shoot for the stars", adding that "if you set the bar low, you're a loser." He's set to hit free agency for the first time in just a few months, and getting him to forgo his right to test the market will obviously take a little extra. And second, while Chisholm's demands are no doubt rich, they aren't as insane as you might think — for reasons that teams and fans might want to pay attention to.

Jazz Chisholm Jr. deserves more praise than he's given

Chisholm is a polarizing player because of how outspoken and confident (at times overly confident) he can be, but are we going to pretend he isn't a great player? In 2025, he slashed .242/.332/.481 with 31 home runs, 80 RBI and 31 stolen bases. He was one of just seven players to go 30-30 last season, and he did so in just 130 games, the fewest of anyone in that club.

He did this while playing predominantly second base, a position that generally lacks much offensive firepower. And not only did he play a premium position, but he did so at a high level, as his 8 OAA at second base (fourth-best mark in the Majors) would indicate. Chisholm was an All-Star, won a Silver Slugger and made a genuine impact in every facet of the game.

Ketel Marte is the best offensive second baseman in the game, but he doesn't defend or run the bases to the level of Chisholm. Marcus Semien and Nico Hoerner were the Gold Glove winners in the AL and NL at the keystone in 2025, but neither player can hit to the level of Chisholm at this point in their careers. An argument can be made that Chisholm is the most well-rounded second baseman in the sport right now, and that's a very valuable player as he enters his age-28 season.

Why Jazz Chisholm Jr. is going to make more money than most expect

I don't expect him to get the $280-350 million he's asking for from the Yankees in an extension, but I do expect Chisholm to get more money than most would expect him to, for a variety of reasons.

Jazz Chisholm Jr. might be the best position player available in 2026-27 MLB free agency

Sometimes, it's about hitting free agency at the right time. Chisholm appears to be doing just that. Look at the players set to hit the open market next winter.

Ronald Acuña Jr. is the best player technically available, but he'll never hit free agency when the Atlanta Braves can simply exercise his $17 million club option. Bo Bichette might be the next best thing assuming Acuña doesn't hit the open market, but is he really going to opt out of the ability to make $84 million over the next two years? Even if he does, while Bichette is an outstanding hitter, he isn't the defender or base-runner that Chisholm is. Chisholm might be the best player on the market even if Bichette opts out.

The best player will get overpaid, no matter the year. Did anyone expect Kyle Tucker to get $60 million annually from the Los Angeles Dodgers? Heck, Dylan Cease cleared the $200 million mark despite posting ERAs over 4.50 in two of the last three years. If Chisholm is seen as the best free agent available, he'll do quite well.

Yankees gave Cody Bellinger a comparable contract

The biggest offseason move the Yankees made this winter was re-signing Cody Bellinger on a five-year, $162.5 million deal. That's an average annual value of $32.5 million, just $2.5 million less than what Chisholm is asking for. The term was shorter, but Bellinger (30) is two years older than Chisholm. An eight-year deal for Chisholm would leave him just one year older than Bellinger will be when his contract ends. Now let's look at their production since the start of the 2024 season.

Bellinger has appeared in five more games than Chisholm in that span, yet Chisholm is the better player in just about every key category. When factoring in this and positional value (second base is more valuable than a corner outfielder, even though Bellinger is a strong defender), why is Chisholm's ask so out of line?

Jazz Chisholm Jr. contract prediction

Whether MLB fans want to admit it or not, Chisholm is one of the best infielders in the sport. That sort of player, who will be under 30 years old when testing free agency, is going to get a ton of money — especially when there are precious few other position players in their prime to spend money on. Chances are, he can either settle on a short-term high-AAV deal like Bichette did this past winter, or he can cash in on a longer contract. I'll predict the latter.

I don't think Chisholm is going to get $35 million annually over eight to 10 years, but I do think that if he has another big year in the Bronx, he's going to get paid handsomely. He might get $30 million annually for seven or eight years, putting him in the $210 million to $240 million range.

Is that something the Yankees can afford to stomach knowing that they're already set to pay guys like Bellinger, Aaron Judge, Max Fried and others long-term? That's up to Hal Steinbrenner to answer. This isn't a player the Yankees should let walk easily, though. Chisholm is harder to replace than anyone would care to admit, and based on his demands, he knows that.

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