3 Trade deadline misses who could’ve saved Red Sox season

Could any trade deadline acquisitions have saved the 2022 Red Sox?

Throughout the fall and at their end-of-season press conference, various members of the Boston Red Sox front office admitted that they regretted various trade deadline decisions.

Not that any of them really made a difference.

To most people who paid attention for even a minute, it was clear pretty early in the season that this wasn’t Boston’s year. Call it a gut instinct or a lifetime of watching this team, but it’s easy to tell when the Sox have that “It Factor,” and they didn’t in 2022.

Between a slew of injuries and plain old underperforming, a lack of quality pitching did this team in more than anything. In that way, it was 2020 all over again; the Sox had many of the fearsome sluggers they’d had on their 2018 championship squad, but without effective pitching, most games got away from them fast and deflating the lineup.

That’s why it was pretty difficult to believe Chief Baseball Officer Chaim Bloom when he opined after the deadline that he thought they’d added pieces who could turn the season around but hadn’t acquired a single pitcher. In fact, they’d actually subtracted a pitcher when they traded Jake Diekman to the Chicago White Sox for catcher Reese McGuire.

But maybe if the Sox had targeted pitching at the deadline, things would be different. The season had unraveled pretty quickly as more injuries piled up in August and September, but perhaps, with different additions, those players’ absences wouldn’t have been the final nail in the coffin.

Here are three pitchers the Sox didn’t get at the deadline who could’ve improved the club in the short (and some in the long) term…

Jordan Montgomery: New York Yankees to St. Louis Cardinals

Starting off with one of the most unrealistic options, because the Red Sox and Yankees almost never make trades. When the Yankees sent Adam Ottavino and Frank German to Boston during the 2020-21 offseason, it was the first trade since the Babe Ruth salary dump that launched an 86-year curse.

Just kidding. But it was only the sixth trade between the rivals since the Divisional Era began in 1969. And since after letting Garrett Whitlock fall into their laps two years ago, the Yankees will be loath to make any substantial trades with the Sox.

Instead, at the deadline, the Yankees sent Jordan Montgomery to St. Louis for centerfielder Harrison Bader, who was injured at the time and didn’t notch his first hit in pinstripes until September 20. His first home run for the club didn’t happen until Game 1 of the ongoing ALDS.

Montgomery had a 3.69 ERA over 21 starts when the Yankees dealt him, and he posted a 3.11 ERA over 11 regular-season starts for his new team, including the first complete game and shutout of his career.

It’s unclear who the Sox could’ve given up to get him. Keep Jackie Bradley Jr. and trade Jarren Duran? Doubtful, though the Sox ended up releasing Bradley and having to pay him to play against them, which wasn’t a great strategy. Maybe Chaim Bloom could’ve somehow convinced them to take Franchy Cordero and Ryan Brasier.

The Yankees would’ve wanted a hefty return. Montgomery is entering his final year of arbitration before becoming a free agent, and that added year of affordable club control enabled the Yankees to ask for more. As evidenced by the moves the Sox did make at the deadline, going the extra mile wasn’t in the cards, no pun intended.

But given the Sox’ rapidly-improving farm system, the money coming off the books this winter, and the gaping holes in the pitching staff both in-season and in next year’s roster, Montgomery would’ve been a smart pick-up. It would’ve taken a lot to get him, but to borrow Bloom’s favorite word, there was a lot of potential “upside,” too.

Raisel Iglesias: Los Angeles Angels to Atlanta Braves

The Atlanta Braves adding Raisel Iglesias to their already-stacked bullpen was just unfair and the Sox got a taste of that not long after, when the Braves came back to their former city for a Fenway series.

While Iglesias had struggled through the first half of the season, posting a 4.04 ERA over 39 appearances, he’d finished 32 games and earned 16 saves. And when his west coast A-team sent him to the east coast A-team, the 32-year-old went back to being lights-out. Over 28 regular-season appearances for the Braves, he had a minuscule 0.34 ERA and his WHIP dropped from 1.065 to 0.835.

Iglesias worked as a starter and reliever in the first two seasons of his career, but since 2017, has solely pitched in relief. Over 351 appearances since that first bullpen-only season, the righty has a 2.80 ERA and 1.051 WHIP. He’s finished 284 games and earned 151 saves.

It’s true that the Sox inked Matt Barnes to an extension in 2021 and gave one to Garrett Whitlock back in April, but Barnes’ extension is only two years with a club option for 2024. The Angels signed Iglesias to a 4 year, $58M extension ahead of the 2022 season.

And let’s be honest: the Boston bullpen just never feels good enough. Alex Cora using his starting rotation for over a dozen innings of relief work in the 2018 postseason run spoke volumes about the state of the late-inning guys. That was one of the best seasons in franchise history, so think about the bullpen every other year. No lead is safe.

While Iglesias did struggle against the Phillies in the NLDS, allowing one earned run on three hits in Game 4, the game was already pretty much won. The Phillies entered the bottom of the sixth with a 4-2 lead and then scored two runs off A.J. Minter before Iglesias came in and allowed a third.

Even if Iglesias hadn’t been able to save the season, it would’ve been great to have him locked in for the next three.

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