Kyle Tucker and 3 more MLB stars now eyeing the exit after trade deadline betrayal

One of the wildest MLB trade deadlines in recent memory has come and gone, and while some teams used that opportunity to load up for the stretch run (and/or temporarily break the internet), others ... appeared to be content to just sort of hang out. For every deadline winner, there must also be a deadline loser — and the latter category might be feeling the effects well beyond the next two or three months.

Because really, what happens in the run-up to July 31 can alter the trajectory of entire franchises. It can make or break front offices. And, in the case of four teams in particular, it can ruin their shot at convincing a foundational star to stick around for the long haul.

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.

1. Kyle Tucker, OF, Chicago Cubs

From the moment Chicago pulled off that deal with the Houston Astros back in December, everything has been geared toward convincing Tucker to stick around for the long haul. And for a while, things were going swimmingly: Powered by arguably the best offense in baseball, the Cubs jumped out to a commanding lead in the NL Central and looked the part of serious World Series contenders, the type of place that any star outfielder would want to call home for the next 10-15 years.

And then the pitching injuries began, and the Milwaukee Brewers got hot, and now Chicago finds itself in a dogfight for the division. How did president Jed Hoyer respond to that pressure? By laying an egg at the deadline, acquiring a back-end arm in Michael Soroka, a utility man in Willi Castro and a middle reliever in Andrew Kittredge. None of them are bad players or fits, but it's hardly the sort of statement fans were looking for.

And it could be what drives Tucker elsewhere come free agency this winter. Maybe it all works out and the Cubs do in fact get to or win the World Series. But this was hardly the best first impression for Hoyer to make, if he wanted to convince Tucker that the North Side was the place that would put him in the best position to compete for championships.

2. Tarik Skubal, SP, Detroit Tigers

Speaking of complacency: The Tigers enter Friday tied for the best record in the AL, with no reason not to get as aggressive as possible to try and make a run to the World Series. But Scott Harris continued to tinker at the margins at the deadline, adding Charlie Morton and Chris Paddack to the rotation to go along with a flotilla of underwhelming relievers (Kyle Finnegan, Paul Sewald, Codi Heuer and Rafael Montero). That's hardly the infusion of talent this team needs to separate itself from the pack.

Which would be bad enough as it is, before even considering the fact that ace Tarik Skubal is about to enter a walk year in 2026. Detroit still seems no closer to signing him to a long-term deal, which makes maximizing this current window even more important. Unfortunately, Harris doesn't think that "windows" exist, and downplayed Skubal's importance when asked about his deadline decisions on Thursday night.

We know how fiery of a competitor Skubal is, and how badly he wants to compete at the highest level. How do you think he's going to respond to a lead executive who twiddles his thumbs at the trade deadline and talks about championship windows as though they're luxuries? If you were Skubal, would you want to likely take less money to stay with this front office in Detroit for the long haul?

3. Paul Skenes, SP, Pittsburgh Pirates

Skenes has likely already made up his mind about leaving Pittsburgh as soon as he gets the chance in a few years' time. But as long as he's under contract, the Pirates have a shot, which is why it's such a shame that they keep blowing it in spectacular fashion.

It's not too far-fetched to think that Pittsburgh could be a Wild Card contender as soon as next season, given how much homegrown pitching talent they have in Skenes, Mitch Keller, Jared Jones, Bubba Chandler and Hunter Barco. But that would require adding some bats to go along with them, and GM Ben Cherington keeps failing to do so. His latest disasterclass: Passing up more highly regarded prospects (by his own admission!) to send closer David Bednar to the New York Yankees, then failing to get anything at all for a trio of veteran free agents-to-be in Isiah Kiner-Falefa, Tommy Pham and Andrew Heaney.

Skenes has made it all too clear how badly he wants to finally play in competitive games in August and September. How can he possibly still have faith that Cherington is the man who can make that happen, or that owner Bob Nutting is willing to make a change?

4. Alex Bregman, 3B, Boston Red Sox

Bregman, by all accounts, has loved his first season in Boston, almost immediately becoming a leader both on the field and in the clubhouse. And the team clearly feels the same, based on how quickly and confidently they dealt away Rafael Devers and handed Bregman the keys to third base for the foreseeable future.

But it remains true that Bregman can, and likely will, opt out of his current deal this winter, entering free agency once again on the heels of what's shaping up to be an excellent season. He's going to have plenty of suitors, and that could cause him to pause and ask himself whether the Red Sox are really where he wants to commit the rest of his prime.

Based on how Thursday unfolded, the answer would have to be a resounding "no". Craig Breslow once again refused to get aggressive and acquire impact talent, instead keeping his powder dry and acquiring a couple of fine but certainly not needle-moving pitchers in reliever Steven Matz and starter Dustin May. If the Red Sox stumble down the stretch, plenty of fans will be pointing fingers, and Bregman will be left asking some awkward questions ahead of the offseason.