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With limited cap space and draft capital, the five biggest questions for 49ers in 2020 offseason

© Cary Edmondson-USA TODAY Sports

Having made it to the Super Bowl and lost, the 49ers’ task is keeping their group together and running it back. It’s not the most straightforward of tasks, given the limited cap space and draft assets they have, which leaves five main questions:

What happens with their three key free agents?

This offseason will be defined largely by whether the 49ers keep their three biggest-name free agents in Arik Armstead, Emmanuel Sanders and Jimmie Ward. In all likelihood, they should be able to retain all three, and keep many of their less renowned, but still important free agents in Ronald Blair III, Ben Garland and Sheldon Day.

In the coming days on KNBR, there will be a more detailed breakdown of every single 49ers free agent and a projection of what type of offer they receive and how the team can fit them under the cap. But for now, the big picture is this:

It seems overwhelmingly likely that San Francisco applies the non-exclusive franchise tag to Arik Armstead (the common one that requires two first-round draft picks to be used as compensation for another team to negotiate with a player) at a projected $17.95 million. The only question is whether — with extensions due to DeForest Buckner and George Kittle, and limited space elsewhere — the 49ers do what the Kansas City Chiefs did with Dee Ford and trade Armstead.

At the moment, it seems the 49ers would prefer to keep him, and they can make that happen with other moves like restructuring Jimmy Garoppolo’s contract, which would also help in retaining Emmanuel Sanders.

When Sanders came to the 49ers, it fundamentally changed the offense, providing two elite pass-receiving threats in Kittle and Sanders, and upping the games of Deebo Samuel and Kendrick Bourne. The 32-year-old Sanders, having played a full decade in the NFL (155 games) plus 47 games in his four-year college career at SMU, has said his main priority is winning. Here’s what he said in his introductory press conference with the 49ers on October 23:

“Once I become a free agent, obviously yeah, [winning] is going to factor in a lot,” Sanders said. “A lot of people don’t understand, yeah the money’s good, I’ve made my fair share of that, but I think it’s it’s about happiness. It’s about happiness, it’s about, is it worth it? Because for me, if I’m just playing for the money and then we talk about longevity, it’s not worth it for me. I love playing football, I love being happy, I love winning games and I think that’s going to be definitely the ultimate deciding factor of where I go.”

So, if it’s really just about happiness and winning games is the “ultimate deciding factor,” the choice should be fairly straightforward as long as the money is fair from the 49ers’ end.

Sanders, who has made $53.85 million in his career, per OverTheCap said in the 49ers’ final locker-room availability that he was both confident the team was set up to win for “a long time” and that, “We’re different. This team is different, this organization is different and it doesn’t start with the players, it starts with the general manager head coach and those guys are special guys, and they’re going to get a group of guys around here.”

“In terms of team chemistry, I’ve never seen anything better,” Sanders said earlier the year on the Murph and Mac show.

Think something like a two-year, $16-to-$18 million deal.

The last one is Jimmie Ward, who finally played a full 16 games. He chuckled when saying that, pointing out that it came through the non-traditional method of three games in the playoffs, but he still played in 16 games. And he was tremendous. While there were so many people to praise on the 49ers’ defense, Ward could easily be argued as the most valuable.

His symbiosis with former high school teammate Jaquiski Tartt on the backend was what separated this defense from good to elite, and after playing on a one-year, $4.5 million “prove you’re healthy” contract, he’ll likely be looking for more long-term security. The question there is, who on the market is going to be willing to pay a player who’s been injury-prone his whole career a deal worth substantially more than what the 49ers are going to be willing to offer?

Sure, the NFL’s elite safeties like Earl Thomas make a killing, but if you’re not verifiably elite it’s often slim pickings. Tre Boston, who’d played four-straight seasons of 14-plus games and was viewed as well above-average before (and including) last season, couldn’t find more than the one-year, $3 million deal he signed with the Carolina Panthers.

There are only 12 safeties in the NFL who make more than $8 million per year, and the top six of them have all been named first-team All-Pro at least once. Only three of those 12 have never made a Pro Bowl (the category Ward falls into). And while Pro Bowls nods are largely flawed, they are used as negotiating tactic by teams, just as injury history is.

It’s unlikely any team offers Ward a deal in that upper echelon. The 49ers are probably wary of giving him a deal too far into the future, depending on how optimistic they are about Tarvarius Moore. If, however, they are willing to offer, say, a two-year, $15 million, or three-year, $20 million deal, it would seem more likely than not that Ward is back.

Can they get extensions done for Buckner, Kittle?

Buckner has to be first. Yes, Kittle is this team’s MVP, but if you deal with him first, that’s an insult to Buckner.

You deal with the guy who has one year left on the deal, and then you move to Kittle. The question is, will the 49ers get deals done with both of them this offseason?

They’ve largely planned their cap situation around those impending deals, and as long as both sides aren’t playing mind games, there’s no reason to believe they shouldn’t get done.

There is a more detailed breakdown of what both Buckner and Kittle would be in line to receive (the numbers used are conservative estimates) here. From a ballpark estimate, think Buckner of receiving an extension that lowers his 2020 cap hit, but gives him a five-year total around $85 million with $40-plus million guaranteed.

Kittle is destined to redefine the tight end market, but it’s unclear if he and his agent want to play the type of hardball to take a monumental deal into cosmic territory. In reality, Kittle should be making what an elite wide receiver does, in the $18 million range, but the tight end market hasn’t fundamentally shifted in years, and it’s held around a top-end yearly average salary of $10 million.

One thing Kittle and his agent may wait on is to see how the contracts of Hunter Henry and Austin Hooper, both 25 years old, play out on the open market. Both figure to make more per year than the $10 million a year that Jimmy Graham currently owns the market with (based on their age and performance, demanding something around $12 million-plus per year), and that probably helps the 26-year-old Kittle’s case for his soon-to-be-record-breaking deal.

The question is, will the 49ers be able to get Kittle closer to $13-or-$14 million, or the vaunted $16-plus million that he probably deserves, but might have to get into some contract warfare to get?

Will they trade down in the draft?

The 49ers have the 31st pick in the 2020 NFL Draft. Then… nothing until pick number 139, acquired from the Denver Broncos along with Emmanuel Sanders, in exchange for a third- and fourth-round pick (the difference in that fourth- and fifth-round pick ended up being 12 spots). That’s a 106-pick gap between San Francisco’s first and second selection, followed by another fifth-round pick, a sixth-round pick and two sevenths.

They could keep that first pick and go for a theoretically higher-ceiling defensive back or offensive lineman, but it seems like a situation that’s begging for the 49ers to trade down for a pair of third-round picks (the now-Las Vegas Raiders have three, the Cleveland Browns have two, the Broncos have two including the 49ers’ original third-round pick, and the New York Jets have two, both in the first half of that round).

There, of course, are other moves the 49ers could make for that first-rounder, like a late second- and a fourth-round pick, but a pair of third-rounders seems like a viable, almost likely move. This is a team that will be run thin in cap space over the next two seasons and needs cheap players. That first-round pick would cost a projected $2.14 million, whereas two third-round picks would cost around $1.65 million (always varies, but that’s the estimate) per OverTheCap.

At a time when every dollar matters, unless the 49ers are truly enamored with a player left in the first round, a trade down makes a lot of sense.

Who stays and who goes at cut-friendly running position?

I’ll include Kyle Juszcyzk in this portion solely because he’s in the backfield and his money matters too. The 49ers have, including Juszcyzk, six running backs on the roster, two of whom cost a significant amount and are arguably the least valuable players in that backfield.

Jerick McKinnon, in all likelihood, will be cut, as will Marquise Goodwin. McKinnon’s cut would leave $4 million in signing bonus money on the books split over the next two seasons, and Goodwin will have $1.25 million left for this season, but cutting the pair now will save a combined $7,186,250. It’s difficult to imagine a scenario in which the 49ers don’t do that.

Raheem Mostert is locked in for another two seasons with team-friendly $3.21 million and $3.51 million cap hits, respectively. Jeff Wilson Jr. is an exclusive rights free agent which means he’ll have to accept the 49ers’ tender of $660,000 or sit out the year.

Then, you have Juszcyzk, playing on the last year of his four-year, $21 million deal and scheduled to have a $6.8 million cap hit this season. That screams an extension, cap hit aside. But there’s also the very real incentive of lowering Juszcyzk’s cap hit for this season via an extension and turning it into bonus money split over the following years.

It could set up for the opposite of Paarag Marathe’s typical contract structure (lots of guaranteed money up front, not much in the back end), with decent guaranteed money in years three and four (if there is a fourth year).

You also have Matt Breida, a restricted free agent, which means the 49ers can offer him one of three tenders (with draft compensation given in the first-, second-, or original round a player is drafted). From San Francisco’s perspective, it’s probably not worth the cost to offer him anything other than the original round tender, though there wouldn’t be any compensation given that Breida was an undrafted rookie:

First Round Tender: $4,667,000

Second Round Tender: $3,278,000

Original Round Tender: $2,144,000

The biggest question mark is Tevin Coleman. Kyle Shanahan loves his ex-Falcons running back, and started him in the last nine regular season games and final two playoff games. He was tremendous at the start of the season and had a 105-yard, two touchdown performance in the Divisional Round against the Minnesota Vikings before dislocating his shoulder the following week against the Green Bay Packers.

Here’s the defining proposition: Is Coleman that much better than Jeff Wilson Jr.? My opinion is that he’s not. At the very least, the gap seems slight, and if it’s not all that significant, the 49ers would be acting fiscally irresponsible to not cut Coleman. That’s harsh, I know, but Coleman, unlike just about anyone else on the team, can be cut with zero dead cap. That means if he’s cut, there’s no financial baggage.

Here’s the kicker: Coleman makes $4.9 million next season.

The 49ers could cut him and offer Breida an ill-advised first-round tender and still be saving money. When it comes down to negotiating those aforementioned extensions and having the valuable asset of any cap space, cutting Coleman for a Mostert, Breida and Wilson backfield seems like the smart decision, especially given the fact that Shanahan has proven capable of turning just about any running back into a great one.

Will replacement coaches be able to continue progress of Browns departees?

Defensive backs coach Joe Woods left Santa Clara for Cleveland to take a defensive coordinator position with the Browns, and he took the “brains” of the 49ers’ defensive line, Chris Kiffin with him. Kiffin, the pass rush specialist for the 49ers, will take over in Cleveland as the defensive line coach.

The 49ers found two replacements for those coaches in Tony Oden, as defensive backs coach and Aaron Whitecotton in Kiffin’s role. Here’s Oden’s path to the 49ers:

After coaching in college for eight years at a number of different schools, Oden got his NFL start with the Texans in 2004 before being hired by the New Orleans Saints as assistant secondary coach from 2006-10 and secondary coach in 2011. He was hired as the Jacksonville Jaguars’ and Tampa Bay Buccaneers’ defensive backs coach in 2012 and 2013, respectively, before spending 2014-17 as the Detroit Lions’ cornerbacks coach and then moving to the Dolphins.

Whitecotton was as assistant defensive line coach with the Buffalo Bills and was there since 2017 (first as an administrative assistant to the head coach, and the last two as assistant defensive line coach). Before that, he had spent four years (2013-16) with the Jacksonville Jaguars as an assistant to the defensive staff, where defensive coordinator Robert Saleh was linebackers coach from 2014-16.

While these don’t seem like monumental changes, Kiffin was key in providing detail and context for defensive line coach Kris Kocurek and relaying information between him and Saleh during the games. Nick Bosa was the one to praise him as the “brains” of the operation and said he was involved in making key in-game adjustments.

Woods signed a one-year deal after being let go after two years as the Broncos’ defensive coordinator and he always seemed destined to get back to that level. His departure won’t go unnoticed. He was praised by players as a tremendous coach and oversaw the 49ers’ growth from a solid to elite secondary after Jeff Hafley, now head coach at Boston College, left for the defensive coordinator position at Ohio State.

To read more about Kiffin, Woods, and the entire 49ers coaching staff of last season, click here.

The 49ers’ got to the Super Bowl on the back of their defense, and it will be up to Oden and Whitecotton to step in effectively to prevent regression.

Final note: Jimmy Garoppolo

He’s going to be the quarterback next year. It’s fun to imagine that Tom Brady is going to steal his protege’s spotlight, but it’s not going to happen. There’s no one on the market that is verifiably much better than Garoppolo and the internal optics of eschewing your quarterback who went to a Super Bowl in his first full season would be disastrous in the locker room.


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