The Cubs signed former Red Sox pitcher Jon Lester in 2014, a move that helped them win a World Series.

White Sox need Bryce Harper or Manny Machado to take a leap of faith

SHARE White Sox need Bryce Harper or Manny Machado to take a leap of faith
SHARE White Sox need Bryce Harper or Manny Machado to take a leap of faith

The White Sox need Jon Lester.

Not the flesh-and-blood Jon Lester. They need the idea of Lester, who, as a big-name free agent, took a leap of faith and a load of money when he signed with the Cubs in December 2014. Is Bryce Harper that big-name free agent? Or is it Manny Machado? Or is it a year early for the Sox and their fans to be bummed out if the franchise can’t land a superstar?

Early? There’s no such thing as early when it comes to a team that has averaged 92 losses the last six seasons. And there’s no such thing as early when a great player is available.

Remember how Lester energized the Cubs’ fan base four years ago? How he brought a presence to a franchise that had been lacking one for years? How the talk suddenly shifted from which prospect would be brought up when to what Lester meant in terms of victories in 2015?

This is how I started my column the day of the signing:

An actual player. A big-time, winning pitcher. A dominant left-hander, for goodness’ sake.

Not a hotshot prospect. Not a new manager. Not a shiny new brick.

A Somebody.

A Cub.

The next day, I had an on-air debate with an earnest radio host after Lester had stunned the baseball world by signing with a team that had gone 73-89 the season before. He argued that there had been joy in witnessing the Cubs’ rebuild, that watching president Theo Epstein do his job was fascinating. He was offended by my apparent dismissal of the construction process at the minor-league level. Why, because I thought waiting for prospects to arrive in Chicago was like watching my toenails grow?

I wanted to watch real major-league players playing major-league games. Just as I want to do with the Sox.

No matter who was right, there was little doubt that Lester’s signing was a turning point in Cubs history.

And this is where the Sox find themselves. If not this season, then next. What a signal it would be to the rest of baseball if either Machado or Harper were to pick the Sox in the next few weeks. It wouldn’t be realistic to think the team could make a 24-victory jump, the way the Cubs did from 2014 to 2015. It wouldn’t be a given that super prospect Eloy Jimenez would win Rookie of the Year honors with 26 homers and 99 RBI, the way Kris Bryant did in 2015.

But you never know. And that’s the wonderful, delicious, hopeful part of this. The Sox have to convince Harper or Machado that the rebuild is about to turn a corner. The Cubs were able to sell Lester on the idea that he would forever be part of franchise lore if they won a World Series. He could be the one who finally put flesh on the bones of a dream. It was a crazy idea. Almost as crazy as the Cubs’ 2016 World Series championship parade turned out to be.


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That’s what the Sox have to sell Harper and Machado on, while other teams sell more immediate objectives. Either can be the cornerstone of something big here. Either can be the man who took a chance on a franchise built on the promise of its minor-league system. And it certainly would be a chance, a gamble. What many people still fail to grasp is how fortunate the Cubs were that so many of their prospects succeeded. And there are no guarantees for the Sox that Jimenez, Dylan Cease, Luis Robert, Nick Madrigal, Dane Dunning and even Michael Kopech will turn into legitimate players. History tells us that.

Career-wise, it’s a roll of the dice for Harper or Machado, but it’s a roll of the dice worth taking. Also, one that will guarantee them about $350 million each. Perhaps this is a good time to lose the risk-taking imagery.

Maybe the Cubs will rip out the Sox’ heart by being the Chicago team that nabs one of the two superstars. It would be a shock, given that Cubs ownership has been sending out strong signals that Harper and Machado are too rich for its blood. A big signing would put the Cubs over the luxury-tax limit, which sounds like a terrible, horrible thing, until you realize that the Red Sox had to pay $11.9 million for going over the limit in 2018. Do you know what $11.9 million is to deep-pocketed franchises like the Red Sox and the Cubs? A couple of Brandon Kintzlers and a season’s supply of sunflower seeds.

The glare of Boston’s World Series rings makes it hard to see if the Red Sox are upset about getting hit with the luxury tax.

Anyway, the White Sox. All it takes is one player to change everything. Lester showed the way for the Cubs. Any superstar out there want to take the wheel for the Sox? There’s an immediate opening.

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