The 49ers were mere minutes away from being named champions of Super Bowl LIV. They fell short, and now they have a lengthy list of offseason obligations to tend to.

It would appear San Francisco has its franchise quarterback, a dominant play-caller and a loaded defense. However, some of the 49ers' best players are either free agents or due for significant raises, and consequently, the team will have big decisions to make, both in number and significance. 

According to ESPN's Bill Barnwell, there are five offseason moves San Francisco should prioritize, all of which could severely impact the team's potential to return to the Super Bowl. Within those five moves, Barnwell advocates for two gargantuan extensions at the expense of two prominent names, and leans into one rumor that just won't seem to die.

So you're telling me there's a chance

While Barnwell concedes that Jimmy Garoppolo likely would have been "both a Super Bowl winner and Super Bowl MVP already" had he not overthrown Emmanuel Sanders late in the fourth quarter of the heartbreaking loss to the Kansas City Chiefs, he believes the 49ers should leave the door open for Tom Brady, in case the six-time Super Bowl champion wants to return to his Bay Area roots.

For numerous reasons, swapping the younger -- and currently superior -- Garoppolo for the considerably older, shadow of his former self that Brady is doesn't make much logical sense, and Barnwell even goes so far as to call the idea "silly", predicting there's a .01-percent chance of it happening. And yet ... cue the "Dumb and Dumber" meme.


So, as unlikely as it might be, how would Brady-to-San Francisco work? Barnwell suggested a potential trade between the 49ers and New England Patriots that would send Brady, the No. 23 and No. 85 picks in the 2020 NFL Draft to San Francisco for Garoppolo and the No. 31 overall selection.

While that would be fair from a trade value chart perspective -- and possibly free up considerable cap space for the 49ers -- Barnwell might have summarized it best.

"Brady will probably be a Patriots quarterback in 2020. Garoppolo will almost certainly be starting for the 49ers. Fun to think about, though."

The extensions

Given San Francisco's current cap situation, it's unlikely you'll see any big names being signed in free agency. That's because the 49ers have their own prominent free agents to sign ... before they hit free agency.

Tight end George Kittle is entering the final year of his rookie contract and is due to hit unrestricted free agency at the end of next season. The same goes for defensive tackle DeForest Buckner. Kittle is the best all-around player at his position in the NFL and Buckner isn't far off, so one would expect it would be an easy decision for San Francisco to sign them both to long-term extensions as soon as possible. Barnwell agrees, and thinks the only question is: How much?

Barnwell suggests Buckner could demand an annual salary in the $18-19 million range, which would slot him in between the Los Angeles Rams' Aaron Donald and the Atlanta Falcons' Grady Jarrett as the highest-paid players at his position. Buckner's fifth-year option will pay him $14.4 million in 2020, so that extension would provide an additional uptick in annual value.

Compared to Buckner, Kittle is due for a much larger increase. He'll make $735k in 2020 in the final year of his rookie deal, but whenever he signs his extension, it will surely reset the market. Barnwell expects Kittle to get a contract extension from San Francisco somewhere around $75 million over five years, which would be far and away the largest contract given to a tight end in NFL history.

Of course, Kittle isn't your average tight end. He is both a tremendous blocker and receiver, and has the stats to back it up. Due to the 49ers' success running the ball with Kittle on the field as a blocker, Barnwell suggested the possibility that Kittle might seek a contract according to a different position's pay scale, such as right tackle. If that's the direction Kittle chooses to go, the 49ers might have to bite the bullet and pay him much more annually than he would receive if he wasn't such a great all-around player.

[RELATED: 49ers' Shanahan, Lynch start to shift focus to 2020 season]

Saying goodbye

Believe it or not, NFL teams aren't (entirely) made of money. If the 49ers are going to keep both Kittle and Buckner long-term, that likely means they won't be able to do the same with some other players they likely would prefer to hang on to.


San Francisco enters the offseason with $19.6 million in projected cap space. More space could be generated by the release of players like Jerick McKinnon and Marquise Goodwin, but regardless, the 49ers likely will have to find less appetizing ways to shed some salary. With that in mind, Barnwell suggested that San Francisco not only let defensive lineman Arik Armstead walk in free agency, but also argued the team shouldn't pick up Solomon Thomas' fifth-year option.

First, Armstead. There's no question the 49ers would prefer to keep him. The former first-round pick is coming off a career-year in which he totaled 10 sacks and 18 quarterback knockdowns; players like that aren't a dime a dozen. But despite San Francisco's desires, re-signing Armstead won't come easy -- or cheap. "It would hardly be shocking if he came away with a four-year, $70 million contract [in free agency]," Barnwell wrote.

Armstead is the best of the team's free-agent defensive linemen, but the 49ers will have to decide if they want to allocate so much salary to one player, or if they'd be better off spreading it around to retain and build depth.

Thomas hasn't shown nearly as much promise as Armstead, and given that his fifth-year option -- if picked up by San Francisco -- would pay him the average of the top 10 players at his position, that should be an easy call for the Niners. Then again, if they let Armstead walk, perhaps that creates a larger need to keep Thomas around beyond this coming season.