Even though they may never acknowledge it, Andy Reid and Jerry Jones have been engaged in a quiet little chess game since Reid dominated the NFC East. During his Eagles tenure, Big Red racked up more wins against the Cowboys than any coach in league history. Not out of vendetta, but out of sheer longevity, Reid once half-joked: “Probably just by chance, just having been in that division so long.”
And yet, he never left Dallas without tipping his visor to Jerry Jones, referring to him as “a great owner” and complimenting the Cowboys organisation for operating “the right way.” But beyond the pleasantries, these two have always stood for very distinct football ideologies, both structurally and strategically. Both Andy Reid and Jerry Jones have long operated in the gray area of the NFL hierarchy, as football executive Andrew Brandt once explained: Jones, an owner who also serves as GM; Reid, a head coach who has historically had the final say over personnel. And while their titles differ, their overlapping power has often come with similar flaws.
Jones’ dual job was characterised by Brandt as “a conflict of personality,” pointing out that Jerry’s financial and emotional commitment, which was excellent for ownership, often conflicted with the aloof, impersonal roster-building that a general manager is expected to do. Reid, meanwhile, struggled in the opposite way. His deep loyalty to players, while admirable, sometimes clouded personnel decisions. Brandt cited Reid’s long-standing trust in Michael Vick as a prime example of personal ties possibly outweighing cold evaluation. Unlike Belichick’s ice-cold detachment, Reid’s player-first approach could work against him when roster resets were needed.
Therefore, it’s never simply football when these two titans, one who likes the splash, the other who values stability, cross paths. Fast forward to 2025, and the right way might just involve cutting right in front of Reid’s draft board.
Reported by multiple outlets, including Brandon Loree and Nick Harris. One of the few Day 1 prospects the Chiefs have seemingly focused on to secure Patrick Mahomes’ blindside for years to come is Josh Simmons. Ohio State’s banged-up but gifted left tackle. However, Jerry Jones and his Cowboys might be getting ready to spoil the fun. As Kansas City gets ready for a potential trade-up. Simmons is not just on the Cowboys’ radar. But he might also be a target in a trade-down situation, according to Brandon Loree. “LB Carson Schwesinger and OT Josh Simmons are two names that could be on the short list of players the #Cowboys could take in the first two rounds. @NickHarrisFWST points out after the clip that Simmons could be considered in a possible trade-down scenario.”
LB Carson Schwesinger and OT Josh Simmons are two names that could be on the short list of players the #Cowboys could take in the first two rounds.@NickHarrisFWST points out after the clip that Simmons could be considered in a possible trade-down scenario.
(: @dallascowboys) pic.twitter.com/25GQ9Rr9y4
— Brandon Loree (@Brandoniswrite) April 19, 2025
Nick Harris agreed, saying that the Cowboys’ coaching staff, in particular linebackers coach Borganzi, had high expectations for two prospects: Josh Simmons and LB Carson Schwesinger. “It’s potential. Linebackers coach, Borganzi worked him out at his pro day. That’s certainly one. Another one that I think cowboys like as much as you guys down the line is Josh Simmons.”
Cowboys insider Voch Lombardi notably highlighted Schwesinger in a recent radio broadcast on 105.3 The Fan, stating: “I just got a feeling the Cowboys love him like I love him.” Nevertheless, it’s evident that Jerry has options. Given that Simmons and Schwesinger are both on Dallas’ board. If Simmons is available when the Cowboys are on the clock. Don’t be shocked if they block Kansas City’s path to Mahomes’ potential bodyguard.
Simmons, who was recently hosted by the Chiefs brass—including Brett Veach and Andy Reid—has become the guy. The long-term plan to protect Mahomes depends heavily on acquiring a legitimate left tackle. And Simmons is widely viewed as a plug-and-play option when healthy. If Jerry Jones pulls the trigger before Kansas City gets a chance. Reid’s major draft objective could be wiped out before the clock even hits Pick 20. And if that happens…
Andy Reid’s draft vision unravels as Chiefs enter panic mode
The Athletic’s @ChiefsBlitz and @ByNateTaylor reported on it. According to reports, the Chiefs, who now own the 31st overall pick, are looking at ways to move up the board. Not just randomly, but with intent. In order to acquire a left tackle like Simmons. Kansas City is actively trying to trade ahead of the Houston Texans and Los Angeles Rams in the first round, according to @ChiefsBlitz.
If they fail? That’s when Veach hits the “Plan B” button. @ByNateTaylor of The Athletic reports that, “ UPDATE If the #Chiefs are unable to acquire Josh Simmons or another left tackle prospect in the first round, Veach could pivot his plans toward selecting an ascending defensive lineman with plenty of pass-rushing juice. Per, @ByNateTaylor, @TheAthleticNFL.” It’s a classic pivot move by Veach, who’s made a name for himself through aggressive draft-day adaptability.
Veach’s recent remarks highlight the vulnerability of this draft approach. There is very little room for error because KC’s board only has 13 non-QB players rated as first-round prospects. If Simmons is missed, the Chiefs may decide to forego Round 1 completely in favour of Day 2 capital. This goes beyond a single tackle. This relates to depth in spots where the Chiefs are rumoured to desire to stack bodies: DE, DT, CB, RB, and OL. What happens if Reid leaves Round 1 without his left tackle? It becomes much more difficult to successfully defend that 2025 crown.
Andy Reid has outlasted dynasties and outcoached legends. But in this particular moment. All roads to roster reinvention lead through a draft night standoff—one that Jerry Jones may already be plotting to win. If Kansas City wants Josh Simmons, they better act fast. Because Jerry’s grinning. And when he’s grinning, someone else’s war room is probably sweating.
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