As trade deadline nears, recent past offers a reminder of dilemma again confronting the Red Sox

As the Aug. 3 trade deadline comes into view, it’s worth looking back a year at a landmark Red Sox trade that could have been, and what that says about the risks and rewards of the buy/sell decisions to come.

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The Red Sox are now officially in the hunt. With Friday’s 6-4 win over the Blue Jays at Fenway Park, they’re 53-49 and hold the second wild-card spot, while having moved within 6½ games of the first-place Rays in the AL East.

“You can at least look up and see the top of the division,” said Sox interim manager Chad Tracy. “It’s in sight.”

The position is similar to the one the club occupied through 102 games last year, when it was tied for the second wild-card spot while sitting six games out of first in the AL East.

The Sox ended up with a deadline fizzle of Dustin May and Steven Matz while whiffing on a much bigger swing. They made a push to acquire All-Star starter Joe Ryan from the Twins. According to multiple sources, the team was willing to send Minnesota its top two prospects: High-A shortstop Franklin Arias and Double-A lefthander Payton Tolle.

Tolle was aware that his name was floating in the rumor mill. He took it as a compliment — particularly given the mentions alongside Ryan — but also recognized the oddity of a situation over which he had no control.

“It was a little bit of uncertainty. It was weird. It was the first time I ever had anything like that,” recalled Tolle. “During the time, I joked — not putting these two on the same level — there were only two people that had any idea of where anybody was going, and that was God and [Red Sox chief baseball officer] Craig Breslow.”

There was another key decision-maker: Twins president of baseball operations Derek Falvey. Minnesota wasn’t willing to consummate the trade of Ryan (who at the time had 2½ years of control remaining) for prospects.

With the benefit of hindsight, the conclusion from that non-deal seems obvious: The Sox are fortunate the Twins turned down their offer.

Tolle has emerged as a staple of the rotation (5-6, 3.31 ERA, 26 percent strikeout rate, 7 percent walk rate). Arias, whose prospect stock has soared into top-10 status in the sport, was promoted after Thursday’s game from Double-A Portland to Triple-A Worcester.

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Both may be critical contributors for years to come. Alternately, the Sox could turn Arias into perhaps the most valuable trade chip in baseball this deadline.

That said, there’s another way to look at the non-trade. What if the Sox had added Ryan last year?

He’d been spectacular through July, with a 2.82 ERA, 29 percent strikeout rate, and 5 percent walk rate. After a Twins teardown at the deadline, Ryan’s numbers (4.89 ERA, 27 percent strikeout rate, 7 percent walk rate, a dozen homers allowed) took a hit.

But those numbers were inflated by a few bad starts. In most outings, he still looked like a front-of-the-rotation pitcher. What if the Sox had added Ryan and slotted him in as the Game 2 starter against the Yankees in the Wild Card Series? Maybe they would have advanced, setting up a matchup with the Blue Jays — a club the Sox had just beat in two of three games at the end of the regular season.

Could the Sox have advanced to the ALDS had they acquired Ryan? The ALCS? The World Series? And how might postseason success — as well as affordable, long-term control of Ryan (once again cooking at an All-Star level this year) — have influenced the team’s aggressiveness last offseason?

Put another way: In a world where the Sox had traded Tolle and Arias for Ryan, it’s possible to imagine a scenario where they would have been thrilled with their deadline boldness. After all, decades after Tigers general manager Bill Lajoie (who became a member of the Red Sox front office in the early 2000s) traded then-prospect and future Hall of Famer John Smoltz to acquire Doyle Alexander, he didn’t regret the deal.

The big leaguer Lajoie acquired had done exactly what he wanted. Alexander led the Tigers to an AL East title, going 9-0 with a 1.53 ERA in 11 starts. Same in 2024 with the Dodgers, who acquired reliever Michael Kopech from the White Sox for infielder Miguel Vargas. Vargas emerged as an All-Star for Chicago this year, but Kopech played a key bullpen role on the way to a title.

Impact additions come at a cost to the future — and often a markup. But timidity rarely yields titles.

How to balance those two concepts? Over the coming days, the Red Sox will have to decide.

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