Will Mike Trout regret remaining with rudderless Angels?

Do you think Mike Trout ever has regrets?

Back in 2019, Trout signed a monstrous 12-year, $426.5 million extension with the Angels that made him by far the highest-paid player in MLB history. At the time, the two-time AL MVP (Trout won his third in 2019) was entering his ninth year in the league, and had experienced postseason baseball just once — when his top-seeded Angels got swept in the 2014 ALDS.

And yet, he committed to staying in Anaheim for what could turn out to be the rest of his career, as his contract takes him through his age-39 season.

Since that 2014 playoff appearance, the Angels have had just one winning season (2015), and haven’t even sniffed October baseball. But that hasn’t stopped Trout from coming out every day, playing the game he loves for the city he loves, and, for the most part, not really saying a word about his team’s struggles. To be fair, he was the one who signed the deal. And he has 426.5 million reasons to be okay with it. But at some point, you do have to wonder: Does Mike Trout have any regrets?

Trout will undoubtedly go down as one of, if not, the greatest regular season baseball player of all time. He has been the unquestioned best player in baseball since he entered the league. But to be considered a “greatest of all time,” you really need to have some postseason experience, and moreover, some postseason excellence on your resume. And in Trout’s lone postseason appearance, he hit a mere 1-12 (.083) with one solo home run and three walks. Not exactly impressive.

Of course, it’s not really his fault he hasn’t had more opportunities to improve upon those numbers. Entering this season, Trout had a career WAR of 76.1. That had him sitting at 75th on the all-time list, ahead of more than 100 current members of the National Baseball Hall of Fame, and many more future inductees. The only active player ahead of Trout in career WAR is 42-year-old Albert Pujols. Trout is only 30.

And yet, the Angels are in the midst of yet another disappointing season, will probably have to trade fellow superstar Shohei Ohtani, and could be headed towards an even more disappointing future.

And this hasn’t even been the worst of it for Trout this season.

On Wednesday, it was reported that Trout was suffering from a rare back condition that could affect him for the rest of his career. The condition, known as costovertebral dysfunction in the T5 vertebrae, could force Trout to completely alter his approach to training, preparation, and even his work in the outfield. There’s no reason to speculate on how this could affect Trout’s performance moving forward — in a perfect world, it wouldn’t change a thing. But a less than 100 percent Trout, while still a dominant baseball player, would put the Angels’ chances at making another postseason run even lower than they already were. And that has to get Trout a little worried.

Just 185 players in MLB history, who have played over 10 seasons in the league, played with one team their entire career. Only 55 of those guys have made it to the Hall of Fame. If Trout finishes out his contract in Anaheim — and he hasn’t said anything yet that would make us think otherwise — he would be joining this exclusive club. And if the Angels continue to struggle, he could be doing it ringless.

In that case, he would be joining an even more exclusive club. A list of players like Carl Yastrzemski, Tony Gwynn, Ernie Banks, and Ted Williams, who toughed it out with one franchise their entire career, yet were never able to bring home a World Series trophy.

Trout could always force a trade (but that doesn’t seem very likely). Or he could play out his contract and then jump to a contender in his age-40 season to win a ring (that’s a possibility). But with the trajectory his team is on right now, it’s pretty apparent that postseason baseball will continue to be played without the greatest player of the last decade. And at some point, you do have to wonder what could have been.

What if Trout didn’t sign that extension in 2019? What if he instead joined a perennial contender and played in multiple World Series? How early in his career could he put himself on the Mount Rushmore of baseball greats if he had just one World Series ring under his belt?

The good news for Trout is he still is only 30. You never know what kind of package the Angels could get for Ohtani if they decide to trade him. And maybe, in the back half of his career, something will click for the Angels. But for now, we get to continue to ask the questions of what could have been. And of course, the most pressing question of them all: Does Mike Trout have any regrets?