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Manny Machado visits the Yankees Wednesday, and Brian Cashman should strike

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Yankees GM Brian Cashman has a chance to put this winter’s top available free agent in pinstripes, and he should do just that.

Manny Machado is the top free agent this winter and the Yankees should grab him while they can. Photo by Patrick Smith/Getty Images

It’s official. Manny Machado is set to visit the Bronx on Wednesday as part of a four-team tour. The coveted free agent will also meet with the Phillies, White Sox, and a mystery team. The Yankees were linked to Machado before the 2018 season even began, but they haven’t been very aggressive in pursuing the generational talent since he hit free agency.

The same can be said about general manager Brian Cashman’s pursuit of other free agents this winter. Although upgrading the rotation was a stated priority, and this offseason’s consensus top free agent starter Patrick Corbin was identified as the Yankees’ top target, Cashman insisted on setting a below-market value price to acquire him and didn’t budge. Cashman reportedly offered Corbin $100 million over five years, and the pitcher signed a six-year pact worth $140 million, slightly more than he was expected to earn.

Nathan Eovaldi was predicted to garner a four-year deal, which is exactly what he got from Boston. Cashman was reportedly unwilling to go beyond three. Similar reports have emerged about his approach to the bullpen, with many of the top arms like David Robertson, Andrew Miller, Zach Britton, and Adam Ottavino expected to receive three-year deals, and Cashman unwilling to go beyond two.

This strategy of under-bidding for top talent in a competitive market obviously hasn’t worked this year. But Cashman hasn’t always taken this approach. In the past, when he set his mind to signing someone, Cashman was uber-aggressive — and it usually paid off.

When the Yankees missed the playoffs in 2008 following 13 straight appearances, Cashman prioritized signing CC Sabathia. The GM famously slipped out of the Winter Meetings to fly to California to meet with the coveted left-hander. He subsequently gave Sabathia and his wife a personal tour of the New York area, and closed the deal by making the Cy Young Award winner an offer he couldn’t refuse.

Cashman also signed the second-most coveted pitcher, A.J. Burnett, along with the top available hitter, Mark Teixeira, that winter. Cashman’s aggressiveness was rewarded, as the trio helped the Yankees win their 27th World Series title in their first season with the team.

More recently, Cashman was equally as aggressive in pursuing NPB standouts Masahiro Tanaka and Shohei Ohtani. He pulled out all stops in putting a team of Yankees executives and stars together to woo each player. The full-court press worked with the former, but not the latter.

It’s time for Cashman to abandon his current strategy, and go back to his old playbook that worked so many times in the past. Machado is in demand — for good reason — and Cashman playing possum isn’t likely to put the star in pinstripes.

Only 15 left-side infielders produced more WAR than Machado (33.8) across their first seven seasons. Wade Boggs tops the list, which includes eight other Hall of Famers like Mike Schmidt, Cal Ripken Jr, and George Brett. The only active players on it are Evan Longoria, Josh Donaldson, and Andrelton Simmons.

For those who still scoff at Machado being labeled a generational talent, consider this: Bryce Harper also entered the league in 2012, but compiled 27.4 WAR over the same exact time frame. Harper amassed 10 WAR during his 2015 MVP-winning campaign, and managed to produce 1.5 WAR or less in three of his seven years in the league.

Machado is arguably the more valuable player, and he has certainly been more consistent. Besides, the Yankees don’t have room for Harper in their crowded outfield. They do have a need for a top-shelf infielder.

We previously reported that the most optimistic prognosis for Didi Gregorius is a mid-season return. However, the average recovery time for players who have Tommy John surgery on their throwing elbows is actually about 12-16 months. So Gregorius could recover more quickly than the average recipient and still miss the entire 2019 season.

Gregorius becomes a free agent following the season, and although Cashman has stated that he would like to sign the star shortstop to an extension, nothing has happened yet. Locking up Machado now gives the Yankees a top player at a premium position for the next several years. If Didi ultimately re-signs as well, that’s even better. It gives the team the option to move the defensively-challenged Miguel Andujar to another position, like designated hitter.

Machado is a five-time All-Star who finished in the top five in MVP balloting twice. He won a pair of Gold Glove Awards at third base, and was awarded the Platinum Glove as the best overall defender in the AL in 2013. Although his shortstop metrics aren’t as strong, that sample size is also much smaller. Any way you slice it, Machado carries both a premium glove and bat.

Perhaps most importantly, Machado is a player on the rise. The 26-year-old posted a career-best .297/.367/.538 slash line in 2018. Most of us are wary of the Yankees handing out fat contracts to players past their primes, but Machado has only just entered his. The first seven seasons of an anticipated 10-year pact would take Machado from his age-26 season through his age-32 campaign, which are typically the most productive years for players.

Left-side infielders who compare favorably to Machado like Boggs, Chase Utley, and Eddie Mathews produced around 50 WAR over their seven-year peak. I’d sure like to see Machado do that while wearing the Yankees pinstripes, instead of a rival’s uniform.

Right now, the Yankees’ projected Opening Day roster is diminished from the one that lost the Division Series. The team is light standouts like Andrew McCutchen, Robertson, Britton, and Gregorius, with the only star addition being James Paxton. Sure, the team could settle for a lesser talent than Machado to replace Didi, and hope to catch a break during the season to avoid yet another second-place finish. Or they can simply grab the best available player now, lock him up for years to come, and head into 2019 ready to challenge Boston’s supremacy in the AL East.

I’m hoping for the latter, and Cashman will have a chance to do just that by signing Machado on Wednesday. It’s time to take the gloves off. Get it done, Cash.