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Chicago Cubs to Save Scott Boras’ Off-Season? Snell and Montgomery Buzz Grows Following North Side’s Bellinger Deal

Published 03/03/2024, 12:29 PM EST

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A favor for a friend or an opportunistic buyout – What’s the difference between the two? Especially for the Chicago Cubs, who were, until a few days ago, at loggerheads with Scott Boras. Now President Jed Hoyer and Boras are seated at the same table and announcing the return of Cody Bellinger to Chi-Town. But that has raised an important question – is Blake Snell or Jordan Montgomery next?

Bellinger’s reintroduction conference showed a rare glimpse. The usually confident and flamboyant Boras looked a little subdued. After months of negotiating, he couldn’t get his client a huge long-term deal. However, Bellinger’s short-term deal did show an important breakthrough for both the Cubs and Boras. Now, with two of his clients still in the market, could the Cubs find a way to bring one of them to their fold?

Favor for Boras or an opportunity for the Chicago Cubs

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When the Cubs let Boras sit at the table with Jed Hoyer, it sent a huge message. Despite their differences, the team didn’t have any ill will against the superagent. While it was a great sight to see, it opened another important door for Boras. Jordan Campbell of the Cubbies Crib has speculated that the Cubs might be interested in Monty or Blake Snell.

As per Campbell, “Snell or Montgomery could prove to be opportunistic deals for the Cubs.” The reasons were simple – the Cubs are barely touching the first taxation threshold of $237 million. The team is currently on a big mission to enter the playoffs, so them breaking that threshold won’t be surprising. Especially if it means strengthening their pitching for the short term.

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The Cubs are already linked with Montgomery. Their case becomes even stronger if the pitcher ends up accepting a short-term deal with many opt-outs (similar to Bellinger). This way, the Cubbies can focus on winning now without having to incur heavy costs in the long term. In a way, this favor to Boras could prove to be a giant opportunity for the North Siders.

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But all of this is possible if Montgomery shows willingness for a short-term deal – which he hasn’t yet. One of the primary reasons is the fact that he might have a suitor who wants to give him a longer deal.

Jordan Montgomery’s Boston links could spoil this party

While the Cubs are linked with Monty, almost all insiders are unanimous in their opinion that the Boston Red Sox are current favorites for him. The team’s flexible payroll plus Montgomery’s current residence in Boston makes them frontrunners. However, one could argue that a deal hasn’t been struck yet, could it mean that there are some issues between the two parties?

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While it’s a giant speculation, it does make some sense. The Cubs have a good pitching staff but adding an elite like Montgomery won’t hurt. With Scott Boras now willing to accept lower-than-expected deals, the North Siders have a giant opportunity waiting for them at their doorsteps.

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Written by:

Sanskar Dubey

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Sanskar Dubey is an MLB writer at EssentiallySports. From writing various aspects of baseball like MLB Rule Modifications to diving deep into the world of minor and major leagues, Sanskar covers it all. He loves to write for the sport when there is a hot tussle between the National League and American League throughout the season.
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Edited by:

Purva Jain