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The Yankees should pursue Manny Machado when he opts out, but probably won’t

If they didn’t sign Machado when he was 26, odds are against them completing a deal after the 2023 World Series, when the Padres’ star will hit the market again.

Championship Series - San Diego Padres v Philadelphia Phillies - Game Five Photo by Matt Thomas/San Diego Padres/Getty Images

The 2018-19 offseason was an eventful one for the Yankees. They had the chance to sign not one, but two generational talents in Bryce Harper and Manny Machado. The latter reportedly preferred to go to the Bronx, but the Yanks let other teams take the lead and he ended up signing a 10-year, $300 million contract with the San Diego Padres.

New York did other things, like signing DJ LeMahieu and Adam Ottavino, trading for James Paxton, extending Luis Severino and Aaron Hicks, and re-signing J.A. Happ, Zack Britton, CC Sabathia, and Brett Gardner. Some moves were steals; others not so much.

Machado was the real prize, though. Perhaps they didn’t want to go to $300 million with him; or maybe they thought they had a third baseman of the future in 2018 AL Rookie of the Year runner-up Miguel Andújar. The fact is that they missed a golden chance to secure a star-level infielder who is excellent at both hitting and fielding for the next decade.

Today, that infielder told media covering the Padres that he will enter the market again after the 2023 World Series. The 10-year deal he signed has an opt-out clause after the fifth season, which is the one that is starting in a few weeks.

In short, Machado is betting that he will make much more than the $150 million he is owed over the next five years given the current market and the increasing luxury tax. His new teammate, Xander Bogaerts, just got $280 million and Machado is arguably better with a couple MVP-caliber seasons to his name.

The Yankees have a rare second chance to sign an incredible player, a Gold Glove-caliber defender with a Silver Slugger offensive profile. And they should, by all means, be in the mix.

The sad thing is that they passed four years ago, and they will most likely pass this time, too.

Machado is still very much in his prime. He is 30, and just had a 7.4 fWAR season with a .298/.366/.531 line, 32 home runs, 100 runs, 102 RBI, and a 152 wRC+. He was a legitimate MVP candidate in the National League in 2022 and will be worth his next contract, which could potentially approach $300 million.

Meanwhile, the Yankees are paying Josh Donaldson and his 97 wRC+ in 2022 to play at the hot corner. Imagining these Yanks with Machado would be extremely fun, but then again, many of the moves they made that offseason probably wouldn’t have gone through if that was the case.

Those 2019 Yankees did alright, going 103-59 and reaching the AL Championship Series. But a player like Machado certainly could have made a difference in 2020, 2021, and 2022.

With 2024 in mind, it’s extremely unlikely that New York will pursue Machado. If they didn’t do it when he was 26, it’s hard to see them making a run at him now with so many potential suitors, growing salaries and several impact young infielders at Triple-A or MLB.

That would be a shame, because that type of player does not become available often. Life is so good and full of twists that if Machado goes through with his intention and opts out, it would give teams not one, but two chances to sign him to a long-term deal during his prime. Take a minute to understand how rare that is.

As good as Anthony Volpe, Oswald Peraza, Oswaldo Cabrera, and Andrés Chaparro may look, the Yanks would be thrilled if one or two of them become even 75 percent of the player Machado currently is.

Of course, Shohei Ohtani will also hit the market unless he is extended. The Yankees’ offense could really use at least one of them from 2024 and beyond, but a deal for any of them feels unlikely for many reasons that go from internal alternatives and, mostly, money. The competitive balance tax (CBT) and its tiers represent a threat to the Yanks’ willingness to spend, and it could end up costing them an elite player once again.