Who’s the better option for Yankees: Freddie Freeman or Matt Olson?

Is this even what the New York Yankees are considering? Rumors suggest so, but we can never be so sure, especially with the lockout having no end in sight.

Over the past week, we learned that the Yankees had talked to the Oakland Athletics about a trade for Matt Olson back in November, but were reportedly unwilling to include either Anthony Volpe or Oswald Peraza in a deal. Then came the bombshell suggesting the Bombers were willing to “make a run” at Freeman when transactions are permitted again.

For some context, if the Yankees go the Olson route, they’ll likely look to also acquire a starting pitcher from Oakland, which would cost them at least four of their top 15 prospects (with three in the top 10). As for Freeman, he’s likely going to land a six-year contract in the $180-$200 million range, which would make for a $30 million-plus AAV.

It depends what the Yankees see as more worthwhile. Does inheriting ~$20 million in payroll, two years of Olson and one year of a starting pitcher from the A’s in exchange for prospects the preference? Or is signing Freeman for money alone and saving prospects for another pitcher trade the more prudent option?

If you ask the average fan, this is a win-win. Trade for Olson and a pitcher? Great. Fills two needs and utilizes a deep farm system that certainly won’t produce 15 or more star players. Pay Freeman? Best first baseman in the game and gives the Yankees a blockbuster acquisition while they likely make a low-budget addition at shortstop to keep the door open for Volpe/Peraza.

If you prefer to know what an MLB insider believes, here’s what Jim Bowden of The Athletic said on the matter recently.

Who’s better for the Yankees: Freddie Freeman or Matt Olson?

"“Freddie Freeman’s going to be six years, whatever it is. You know, six years, $180 million, $187 million, $190 million. Somewhere around there, right? I love the fit for the Yankees. I love him in that stadium. He can handle New York. He’s a winning player. I absolutely love him in the middle of that lineup,” Bowden said on MLB Network Radio.“Now, shortstop’s a problem but you can still trade for Matt Chapman, put him at shortstop. Or you just wait for Anthony Volpe or Oswald Peraza to be ready. The reason I like Freeman over Matt Olson is that I don’t have to trade Volpe or Peraza in a package to get him. Gotta have a left-handed hitter on that team.”"

Shortstop is technically a problem, but the Yankees can get by putting a good defender there if they address their lineup issues with Freeman and one more above-average depth bat. As for Freeman’s contract situation, though, that could make the front office a bit hesitant.

Do they want three $30 million AAV salaries on the books from 2023-2025 (Giancarlo Stanton and Gerrit Cole, too!) plus whatever Aaron Judge will be making when his new contract extension arrives? We can assume that’ll be at least $25 million per season. Though ~$70 million (and maybe more) will be coming off the books after 2022, the Yankees are still stuck with paying ~$25 million per season for DJ LeMahieu and Aaron Hicks from 2023-2025 as well. Compare that with just two years and ~$28 million total for Olson (with first dibs on re-signing) and you can see the difference.

It all depends what the Yankees view as more risk averse. From a performance standpoint, the only thing that separates these two sluggers is Freeman’s consistency, pedigree and overall body of work — they’re both lefty sluggers who play Gold Glove-caliber defense. So do they want to prioritize crunching the budget and addressing another area of need or going for the jugular and holding onto their prospects for another deal/building a more cost-effective roster later down the road?

Either one is a massive victory, but the plan that follows will determine whether it was the right move or not.

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