The arrow is very much pointing up for the Boston Red Sox right now. Craig Breslow finally found a way to make an offseason splash, acquiring ace Garrett Crochet from the Chicago White Sox (and then locking the lefty up with a new long-term deal) before landing third baseman Alex Bregman at the 11th hour of free agency. And those moves have paid early dividends: After a sweep of the St. Louis Cardinals over the weekend, Boston has now won five games in a row, looking every bit the part of an AL East contender.
And for as exciting as the present is at Fenway, it's hard not to start peeking ahead to the future. Kristian Campbell already looks like a burgeoning star less than two weeks into his MLB career, with fellow top prospects Roman Anthony and Marcelo Mayer hot on his heels. Plus, the team had still managed to largely keep its financial powder dry, setting up an anticipated run at arguably the biggest name in next year's free-agent class: star Toronto Blue Jays first baseman Vladimir Guerrero Jr., seemingly destined for the market after failing to sign a contract extension this winter.
If you were to draw up the ideal target for Boston, it'd look a lot like Vladdy. A marketable star in one of the game's marquee markets, still just entering his prime? Check. A righty power bat who would wear out the Green Monster? Check. An already-established love for torturing the New York Yankees? Check. Sure, it wouldn't come cheap, but Guerrero Jr. is the sort of player you pony up for.
Alas, that dream now appears to be dead. Against all odds, Toronto managed to convince Vladdy to stick around for the long haul, handing him a 14-year, $500 million deal that will likely keep him in Canada for the rest of his career. Just like that, Boston is back to the drawing board, looking to find another way to vault themselves into years of World Series contention.
But it's not all bad news. There may not be another on-paper fit as neat as Guerrero Jr. would have been, or another player who combines his sort of talent and relative youth. Still, we know Boston has money to burn, and there's no shortage of options for Craig Breslow to consider.
4. Trade for Luis Robert
Robert isn't nearly the offensive force that Guerrero Jr. is, and he's off to another slow start this season after slogging through a miserable, injury-plagued 2024 campaign. But the 30-30 potential he displayed in 2023 looms large, and he won't be 28 until August. Plus, he checks the right-handed box, and he'd give Boston a true center fielder that would allow Jarren Duran to remain in left and would put less pressure on Ceddanne Rafaela.
Again, there's certainly risk here. But it's hard to shake the feeling that Robert is a sleeping giant; he's been the only viable bat in a terrible Chicago offense for 18 months now, and that's almost certainly started to wear on him and his approach at the plate. But him in an ideal hitter's park surrounded by other threats, and we could finally see what his ceiling looks like. With two team-friendly options still to come in 2026 and 2027, he could be a bargain.
3. Sign Pete Alonso
Alonso isn't in Vladdy's tier as a player, both because of his declining offensive profile and because he's already on the wrong side of 30. But he's still got plenty of juice left in the bat, as he's proven with a torrid start to 2025. He's also a perfect fit for Fenway, peppering balls off the Monster while still having enough power to use all fields.
Guerrero Jr. taking himself off the market may up Alonso's asking price a bit, especially with Scott Boras leading the way. The presence of Kyle Schwarber, Marcell Ozuna and maybe even Cody Bellinger or Luis Arraez could dampen that, though, and the league still doesn't figure to be thrilled by the idea of a long-term deal for a player who will be 31 in December and was never particularly athletic to begin with. The Sox could get Alonso for a relative bargain, getting another 40 homers out of him before pivoting elsewhere down the line.
2. Go all-in on pitching
The reality is that next year's crop of hitters isn't particularly strong, especially if you're looking for righties; after Vladdy, the list is pretty much Ozuna, Bo Bichette and Eugenio Suarez, none of whom figure to excite Boston all that much.
But the Red Sox also need as much pitching as possible, even with Crochet locked up, and there will be loads available this winter. Breslow could get a jump on the market by trading for, say, Miami Marlins ace Sandy Alcantara — whose high ground-ball rate makes him a great fit for Fenway — or take some of that Guerrero Jr. money and try to sign both a frontline starter (Dylan Cease? Michael King? Brandon Woodruff?) and a lights-out reliever (Devin Williams? Ryan Helsley?). The ascension of Anthony and Mayer may obviate the need for another star bat, allowing Breslow to spend big on pitching while adding another righty to the lineup for cheaper.
1. Kyle Tucker
Of course, there is one other bonafide star set to hit free agency. He might not be as clean a fit as Vladdy would've been, and it would create some awkward questions if Anthony hits the ground running as a corner outfielder in Boston at some point this summer. But if there's a player worth making it work for, it's Tucker, who also happens to hit lefties almost as well as he hits righties and has enough power to play in any ballpark.
It won't come cheap; with Guerrero Jr. off the market, every big-market team is going to be lining up to poach Tucker from the Chicago Cubs. This is the cost of doing business at the top of the sport, though, and if Breslow wants to keep up with the Joneses, he might have to take a plunge he's not entirely comfortable with.
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