The NFL does not really believe in goodbyes. It believes in pivots. One moment, you’re watching the final confetti settle on a completed season; the next, you’re refreshing your feed for trade rumors and contract restructures. With 2025 officially in the past, the league has already slipped into its favorite offseason pastime: imagining big moves before they happen.
And somewhere sits a pairing that feels almost too on-brand to ignore, the Philadelphia Eagles and Maxx Crosby.
Howie Roseman Predicted To Bring Eagles and Maxx Crosby Together
If the offseason had a main character, it might be Howie Roseman, equal parts spreadsheet savant and chaos enthusiast. Around the league, executives have learned that when an incredible player even hints at availability, Roseman will at least make a call. Sometimes he makes two.
That’s why Crosby’s situation with the Las Vegas Raiders feels less like idle chatter and more like foreshadowing, according to a prediction by CBS.
Crosby, the high-motor edge rusher who has built his reputation on effort as much as production, experienced a slightly awkward ending to the 2025 season. The Raiders shut him down late in the year, which reportedly did not thrill him.
However, recent reports suggest both sides are now in a “great place” as Crosby rehabs from meniscus surgery.
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Meanwhile, in Philadelphia, there’s a quiet urgency. The Eagles made a midseason push to repair their pass rush, acquiring Jaelan Phillips in hopes of igniting a defense that had been flirting with mediocrity in pressure rate and sack totals. It worked, the unit stiffened, found rhythm, and rediscovered its bite.
But Phillips is going to hit free agency soon. And championship windows, as Philadelphia knows well, don’t stay open forever. This is where the All-Pro athlete has interested them.
He’s under contract through 2029 after signing a three-year, $106.5 million extension in 2025 that included $91.5 million guaranteed. In 2026, he’s due $30 million in base salary with a cap hit nearing $36 million. The guarantees taper after that season, which creates wiggle room, and Roseman has made a career out of finding wiggle room where others see walls.
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The trade market precedent isn’t subtle either. When Micah Parsons was traded from the Dallas Cowboys to the Green Bay Packers, the return package was big: two first-round picks plus defensive tackle Kenny Clark.
Crosby is slightly older; he’ll be 29 when next season starts, and coming off a meniscus repair, which may soften the asking price. But “soften” in this context likely still means a first-round pick and premium additional compensation.
For Philadelphia, that could translate to its 2026 first-round selection and a Day 2 sweetener. Painful? Yes. Paralyzing? Not for a team that sees itself squarely in Super Bowl conversation.
