Jordan Montgomery asking price leaves little optimism for Chicago Cubs signing

With reports this past weekend that the Chicago Cubs were expected to become the most aggressive team in baseball, reports on Jordan Montgomery's asking price are sure to halt Jed Hoyer in his tracks. Per Bleacher Report, Montgomery seeks a contract that tops Aaron Nola's 7-year, worth $172MM.

There is no way Hoyer gets up to seven years for a starting pitcher. On top of that, it seems unlikely that Montgomery will take a short-term, higher-AAV deal this winter. Now, at age 31, he wants his guaranteed payday. Where the Cubs have grown fortunate on the Cody Bellinger front in several teams not really in on his services this winter, many competitive teams are still looking for viable starting pitching entering 2024.

Montgomery is another Scott Boras client, so it won't surprise me to see Montgomery land something near his asking price. To land any top free agents remaining on the board this winter, you must go through Boras. After Shota Imanaga, the following five best free agents are all Boras clients in Bellinger, Rhys Hoskins, Matt Chapman, Blake Snell, and Montgomery.

Scott Boras' price-gouging brought on by Nola deal

When the Phillies signed Nola to that seven-year, $172MM deal, Boras' eyes lit up like Christmas trees as it set the bar for starting pitching high this winter. Nola has high potential, but the fact remains that he carries a 4.09 ERA over his last three seasons. Compare that to Montgomery's 3.48 ERA over the past three in retrospect; you see why Boras' asking price is so high for his client.

Still, this is the deep water that Hoyer won't enter this winter. The only way to get creative enough with the contract structure would be a much higher AAV over the first three years, with an opt-out likely needed after the second year. It could be done, in theory, but the odds are the Cubs won't be the only team trying to offer a sweet deal. Once it eventually goes to bidding wars, expect the Cubs to bow out so as not to affect the future. You can't blame Hoyer for not wanting to have potential dead weight on the roster four years from now if you can avoid it.

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