The San Francisco 49ers’ offseason is shaping up to be a high-stakes chess match, and Kyle Shanahan isn’t just moving pawns. Rumors swirl like fog over the Golden Gate Bridge, teasing twists that could redefine the team’s identity. At the heart of it all? A fiery playmaker itching for a fresh start and a linebacker whose future hangs by a thread. Buckle up—this saga is far from boring.

The 49ers plan to release Deebo Samuel with a Post-June 1st designation, saving $5.1M in cap space. Trading him would cost $15 million, a financial no-go for a team eyeing extensions for stars like Brandon Aiyuk. ESPN’s Jeff Darlington summed it up.

“I don’t anticipate that the 49ers will get a lot for Samuel because he is also going to have to need to be extended. And it’s pretty clear that the 49ers will likely have to cut him if they don’t trade him, so they really don’t hold much leverage here.” Darlington said. Meanwhile, Samuel’s trade request, reported by Adam Schefter ahead of the Super Bowl, adds fuel to the fire.

“I have to do what’s best. I’m more than thankful for the Niners giving me the opportunity of a lifetime, but now I think it’s best that we find another team,” Samuel admitted, hinting at frayed ties with Shanahan.

Once a Swiss Army knife for San Francisco—1,770 scrimmage yards in 2021—Samuel’s production dipped to 806 yards in 2024. Yet, his dual-threat prowess still tempts contenders. Teams like the Broncos, Chargers, and Ravens could gamble on a rebound. Denver, linked heavily, fits Samuel’s desire for a dangerous squad. “You need a couple more pieces, and it’ll be what it need to be,” he teased about the Broncos. But is Deebo Samuel still the piece?

Five teams stand out for Samuel:

1. Broncos: Sean Payton’s creativity + Bo Nix’s growth = a match.
2. Chargers: Jim Harbaugh’s run-first style mirrors Samuel’s 49ers role.
3. Colts: Pairing him with Anthony Richardson’s legs creates chaos.
4. Commanders: GM Adam Peters, a 49ers alum, knows Deebo’s value.
5. Ravens: Lamar Jackson and Derrick Henry? Add Samuel, and defenses sweat.

But buyer beware: Samuel turned 29 in 2025, and a $15.4M option bonus looms. “He is also going to have to need to be extended,” warns Darlington. For San Francisco, cutting losses now might sting less than a messy divorce later. And while Deebo dominates headlines, Dre Greenlaw’s free agency quietly simmers.

Dre Greenlaw: Heartbeat of Kyle Shanahan’s defense

The linebacker’s torn Achilles in Super Bowl LVIII clouded his value, but his impact when healthy is undeniable. Fred Warner, his partner-in-crime, pleaded, “Oh, man, as bad as anybody. That’s the guy, I feel like, that has allowed me to ascend in this league… because of his ascension and the type of player that he is.” Shanahan echoed.

“We’re doing everything in the world we can to bring Greenlaw back,” Shanahan said. Yet, money talks. With $48M in cap space but Brock Purdy’s megadeal looming, Greenlaw’s return isn’t guaranteed. Meanwhile, the Commanders, led by ex-49ers exec Adam Peters, could poach him.

“Dre Greenlaw wants the opportunity to run his own shop,” notes The Athletic’s Matt Barrows. If he bolts, San Francisco might target Chargers’ Troy Dye—a cheaper, special teams-savvy alternative.

The 49ers’ offseason hinges on balancing sentiment and strategy. Letting Deebo walk avoids cap hell but robs the offense of its swagger. Losing Greenlaw weakens a defense already reeling. Yet, both moves could fund Purdy’s future and inject youth via the draft (hello, OT Josh Simmons and DE Nic Scourton).

As Kyle Shanahan navigates this tightrope, one question lingers: Will loyalty cost the 49ers their edge—or can they rebuild without losing their soul? What’s riskier: betting on fading stars or starting fresh?