Dak Prescott had his best professional season in 2019, and from a statistical standpoint was one of the top quarterbacks in the league. But in actuality, was far more inconsistent than the numbers indicate, with Prescott often struggling against good teams and in crucial matchups (see Week 4 vs. Saints, Week 12 vs. Patriots, Week 13 vs. Bills, Week 16 Evs. agles). While Prescott will likely be given a lucrative contract extension this offseason, the organization may at least consider alternative options ( via the draft, maybe even Tom Brady). With Jason Garrett gone, the ire of the Cowboy fans will now be focused on Prescott if the team continues to disappoint. Backup Cooper Rush is a free agent and I expect the team to look for an upgrade. Clayton Thorson, a 2019 5th round pick of the Eagles, spent the year on the practice squad and has some theoretical upside. You have to assume Jerry Jones will pay to keep Dak in Dallas, but with a new Head Coach (who prior to taking the job said he would prefer working with a rookie QB over a veteran), an intriguing draft class (Tua Tagovailoa, Justin Herbert, etc), and an even more intriguing free agent QB pool (Tom Brady, Jameis Winston, Teddy Bridgewater) perhaps something unexpected will happen.
Need Level: Very High
Free Agency Preview at Quarterback: Free Agent QB options include Tom Brady (who, at least on paper, would be an awesome fit in Dallas), Jameis Winston (a beautiful disaster), and Teddy Bridgewater (who was impressive in relief of Brees last year). In terms of backup QB options, the Cowboys could consider experienced vets like Chase Daniel, Case Keenum, and Mike Glennon. Note that Mike McCarthy did draft Brett Hundley (who served as Kyler Murray's backup in Arizona last year) in 2015.
Draft Preview at Quarterback: If the Cowboys shock the world and draft a QB there will be a number of interesting options, including Tua Tagovailoa, Justin Herbert, Jordan Love, Jacob Eason, Jalen Hurts, and Jake Fromm. Though if they want Tagovalio or Herbert they'd almost certainly need to trade up.
I don't quite understand the "down" year critique for Ezekiel Elliott, he scored 6 more rushing touchdowns and averaged only 0.2 yard less per carry than he did in 2018. Needless to say, Zeke is still one of the league's best. 2019 rookie Tony Pollard was a revelation as the #2 back, he averaged over 5 yard per carry and added an explosive element to the offense. Mike Weber, a 2019 7th rounder who spent the year on the practice squad, will have to earn the #3 spot this offseason.
Need Level: Low
Free Agency Preview at Running Back: Not applicable.
Draft Preview at Running Back: A late round pick could be used on a back to compete with Weber for the #3 job.
While all signs seem to pointing to an Amari Cooper resign, it's important to keep in mind that the Cowboys only have one franchise tag - which in all likelihood will be earmarked for Dak, meaning if a deal is not reached between the Cowboys and Cooper prior to the start of free agency - Cooper will be free to explore the market. While Cooper has been a very productive receiver for the Cowboys, the organization may have some reservations about handing him a long term, set the market type contract, considering his inconsistent tendencies. #2 WR Michael Gallup took a big leap in year 2 and some now consider him to be a WR1 caliber player. He certainly flashed that upside on somewhat consistent basis in 2019. Randall Cobb was an effective slot man and developed a strong chemistry with Prescott as the year wore on, I assume the Cowboys will be interested in retaining him, though he may have the option of getting paid more elsewhere. Outside of a few splash plays here and there, the Tavon Austin experiment hasn't been very fruitful, I expect the Cowboys to let him walk in free agency. Deep reserves like Cedrick Wilson Jr. and Noah Brown will be fighting for a job this summer.
Need Level: High
Free Agency Preview at Wide Receiver: In the off chance the Cowboys don't resign Cooper, they could pursue more affordable options like Robby Anderson or Breshad Perriman. If they want to go the older, vet route, A.J Green and Emmanuel Sanders should be available. Possible low risk fliers include Nelson Agholor and Devin Funchess. Keelan Cole would be a possible replacement for Cobb (if he leaves).
Draft Preview at Wide Receiver: If Cooper leaves the team the Cowboys will likely consider a WR in the first round, the draft class at the position is historically strong and includes studs like Jerry Jeudy, CeeDee Lamb, Henry Ruggs III, Tee Higgins, and Laviska Shenault Jr. Day 2 prospects include Jalen Reagor and KJ Hamler, either of them who would add a lot of speed to the WR depth chart.
Jason Witten is a Cowboys (and NFL) legend, but last year did nothing more than impede the progress of the younger, more dynamic Blake Jarwin, who is now a restricted free agent. I think Jarwin has the talent to put up big numbers if trusted with the starting job. The #2 by default is Dalton Schultz, a 2018 4th rounder who has done next to nothing in his 2 years with the team. Perhaps the removal of Witten will open things up for him. Still, the Cowboys need to add depth and competition to this spot in 2020.
Need Level: Mild
Free Agency Preview at Tight End: Jarwin is a restricted free agent and depending on the level of tender, he could generate some interest on the market. If the Cowboys want to move in another direction, they could target big names like Austin Hooper, Hunter Henry, and Eric Ebron.
Draft Preview at Tight End: The top of the Tight End draft class consists of Brycen Hopkins (Purdue), Cole Kmet (Notre Dame), and Hunter Bryant (Washington).
Tyron Smith continues to be one of the league's best left tackles, but he hasn't completed a full 16 game season since 2015 due to a variety of injuries. The organization would be wise to begin the process of developing his eventual replacement. If there is a weakness on the Cowboys offensive line, it is a Left Guard where 2018 2nd rounder Connor Williams was nothing more than average in 2019 and tore his ACL late in the season. Travis Frederick had a triumphant return from the medical scare that cost him his 2018 season and gives the Cowboys a rock solid force at center. Like Tyron Smith, Zack Martin is one the league's best offensive lineman, but he too has missed time with a lingering back/neck issue that may never really go away. Right Tackle La'el Collins broke out in 2019, and established himself as one the league's better Right tackles. In terms of depth, the Cowboys have Connor McGovern (an offensive guard and 2019 3rd rounder who missed his entire rookie season with a hip injury), swing tackle Cameron Fleming (who struggled in relief of Smith last year), Joe Looney (an experienced and decent backup interior lineman), and Mitch Hyatt (2019 UDFA who the Cowboys reportedly believe has a bright future).
Need Level: Mild
Offensive Line Free Agency Preview: The Cowboys may scan the market for low risk, reclamation projects, who could serve potential swing tackle upgrades. This list could include Jason Spriggs (who McCarthy selected in the 2nd round back in 2016) and Cedric Ogbuehi (a 2015 1st rounder).
Offensive Line Draft Preview: I doubt the Cowboys address OT in the first two rounds of the draft, but it they do possible targets include Tristan Wirfs, Mekhi Becton, and Josh Jones. The team is more likely to being target the position in the 3rd round, when prospects like Prince Tega Wanogho, Isaiah Wilson, and Trey Adams may be available.
The Cowboys defensive line and pass rush was average in 2019 (19th in terms of sacks and 10th in terms of least rushing yards allowed). The stalwart of the unit was Robert Quinn, an impending free agent who recorded 11.5 sacks. At the other end spot is Demarcus Lawrence (5.5 sacks), who had a solid season but underperformed relative to the massive contract extension he signed last offseason. The defensive tackle starters were Maliek Collins and Antwaun Woods. Collins has had a relatively underwhelming 4 seasons with the team, while Woods is an upgradeable nose tackle. I think it's time for the Cowboys to move on more the perennially injured Tyrone Crawford. Reserves on the line like Trysten Hill (2019 2nd rounder), Dorance Armstrong (2018 4th rounder), and Joe Jackson (2019 5th rounder) have theoretical talent but have yet to prove their worth.
Need Level: High
Defensive Line Free Agency Preview: Dorance Armstrong (2.5 career sacks) would the presumed starter at DE if Robert Quinn walks in free agency. Needless to say DE is a sneaky need for the Cowboys. Free agent options include include Yannick Nqokoue, Jadeveon Clowney, and Dante Fowler - though all three may be outside the Cowboys price range. More realistic options could include Olivier Vernon, Emmanuel Ogbah, Carl Nassib, Jabaal Sheard, and Ronald Blair. Of course the easiest path would be to retain Quinn in the first place. The Defensive Tackle class is loaded and consists of Chris Jones, D.J. Reader, Arik Armstead, Leonard Williams, Michael Pierce, Michael Brockers, Damion Harrison, A'Shawn Harrison, and Quinton Jefferson.
Defensive Line Draft Preview: Top DTs in the draft include Javon Kinlaw, Ross Blacklock, and Neville Gallimore. Top DEs include AJ Epenesa, K'Lavon Chaisson, and Yetur Gross-Matos.
Jaylon Smith and Leighton Vander Esch make up an exciting young core at the LB position. Though there has to be some concern over Vander Esch's neck - it cost him 7 games in 2019 and some teams reportedly left him of their draft boards because of neck concerns. Depth at the posistino is an issue, with Sean Lee, Joe Thomas, and Justin March all scheduled to hit free agency. Leaving the team with unproven backups like Chris Covington (2018 6th rounder) and Luke Gifford (2019 UDFA). Lee proved serviable in 2019 but at his age and with his injury history the team would not be wrong to move on. Thomas, is an experienced reserve who the team could have some interest in retaining.
Need Level: Low
Free Agency Preview at Linebacker: New Cowboys DC Mike Nolan was previously the LB coach for the Saints and could target some of his former players like, AJ Klein and Stephone Anthony.Other, higher quality options exist in the form of Nick Kwiatkowski and Joe Schobert. OLB Haason Reddick (the 14th overall pick by the Cardinals in 2017) is rumored to be on trading block and would be a very interesting reclamation project for the Cowboys.
Draft Preview at Linebacker: Unless the Vander Esch neck situation is more serious than we currently know, I don't see the Cowboys selecting a LB until Day 3.
The secondary was the Cowboy's worst unit in 2019. At CB, Byron Jones was superb (outside of his 0 INTs), Chidobe Awuzie took a step backwards, and Anthony Brown missed a big portion of the season due to injury. While Jourdan Lewis played well, his snaps were limited due to former DB coach Kris Richard's ridiculous size > player mindset. As it stands now, both Jones and Brown are set to hit free agency. At Safety, Xavier Woods had a solid year and established himself as a key member of the defense, while Jeff Heath (who is not a starting caliber player) predictably struggled. 2019 6th rounder Donovan Wilson wowed in the preseason but wasn't given much playing time once the regular season actually began. So in review, the Cowboys need a new starter Safety and need to at least bring on some starting competition at CB.
Need Level: High
Defensive Back Free Agency Preview: The Cowboys should at least try to retain Byron Jones, but in the event that he does leave, James Bradberry, Chris Harris, and Bradley Roby are possible replacements. Potential buy low candidates include Jalen Mills and Ronald Darby (two injury prone Eagles CBs who are talented when healthy). The Cowboys could also kick the tires on big name older vets like Josh Norman and Aqib Talib. At Safety the crown jewel is Justin Simmons, though the Broncos are expected to bring him back, so the Cowboys may be looking at names like Karl Joseph, Anthony Harris, Jimmie Ward, Ha Ha Clinton Dix, Damarious Randall, Tony Jefferson, and Vonn Bell (who Nolan knows from the Saints).
Defensive Back Draft Preview: CB options (outside of Jeffrey Okudah, who will be gone long before the Cowboys select at #17) inluce Kristian Fulton, Trevon Diggs, CJ Henderson, Bryce Hall, and AJ Terrell. Safety possibilities include Grant Delpit and Xavier McKinney.
Kai Forbath was solid in relief of the disaster that was Brett Maher. But Forbath's career has been defined by inconsistency and he needs competition for the job. Punter Chris Jones had a down year and probably needs to earn his job as well.
Need Level: Medium
Special Teams Free Agency Preview: Greg Zuerlein has been one of the better Kickers in football over the last few years and has a long history with the Cowboys new ST coach John Fassel - he'd be a nice addition. Kai'imi Faibairn is also one of the league's better kickers and considerably younger than Zuerlein. There does not appear to be an obvious upgrade at punter.
Special Teams Draft Preview: Rodrigo Blankenship is considered the best kicker in the draft class, while Branden Mann is considered the best punter.