What would it take for Angels to keep Mike Trout for years to come?

The outfielder is consider the best baseball player on the planet

Mike Trout is the best player in baseball. He's also smack in the middle of his prime at age 27. And he's due to hit free agency after the 2020 season, when his current six-year, $144.5 million contract runs out. That puts the Angels at something of a crossroad over the next 18 to 24 months.

Will the Halos be able to afford extending Trout a second time, with what almost certainly would have to be a massive, record-breaking deal? Or will they ever actually consider trading their franchise face? Fabian Ardaya of The Athletic considers this in a deep dive into where things stand between the Angels and Trout (subscription required).

For an extension, the expectation would be that Trout could command more than Giancarlo Stanton's $325 million contract -- the largest in history to date. And obviously, whatever happens with Bryce Harperand Manny Machado -- the two top names on the open market this offseason -- is going to impact the cost of signing Trout beyond 2020, too.

A long-term pact takes two to tango, so to speak. "I think it just gets to having overlap," said Dodgers president of baseball operations Andrew Friedman, who previously served as general manager of the Rays when he signed Evan Longoria to a six-year, $100 million extension in 2012.

"It's the player really wanting it, the team really wanting it. Usually, when that's the case, you can find an overlap. There are just different points in time where that may not line up perfectly and then it's obviously harder."

And if there isn't overlap, maybe because Trout would prefer to test free agency two years from now rather than re-upping before then?

"The Angels have said emphatically they will not trade Trout," Ardaya writes. "But what if they don't feel they can keep him?"

It's not as if the front office hasn't tried hard to build a winning team around Trout. Big money has been spent on Albert Pujols, Josh Hamilton, C.J. Wilson, Justin Upton and others -- and yet the Halos have made the postseason just once with Trout: a three-game sweep at the hands of the Royals in the 2014 ALDS.

"I could argue that the Angels have tried," said former Marlins president David Samson, who played a big role in Stanton's contract and now is an analyst for CBS Sports.

"But Trout cannot guarantee the Angels a ring. He is the face of that franchise, and it is a brutal thing to think about, but if you're not going to win, then paying him that amount of money may not be the best thing for your team's chances to win. But it hurts like hell to lose a player like that."