Drew Brees (41): 

Brees is one of the easier free agent targets to predict in the quarterback position. I don’t see any scenario where he leaves New Orleans, despite the team’s high praise of super utility quarterback Taysom Hill. While Taysom Hill may also be a priority re-signing of the Saints, look for Brees to sign a one or two-year deal with the team as well.

Prediction: 2 years- 56 million. 34M guaranteed 

Dak Prescott (26):

Prescott is in a tricky situation with the Dallas Cowboys. He wants 40 million dollars a season, and he’s not going to get that. Nor should he. The Cowboys could look to franchise tag Prescott and then trade him, while singing Tom Brady, if Brady does in fact leave New England. Brady’s departure from New England is a very strong possibility, and the Dallas Cowboys to me would be the best fit for him. The Cowboys have a team that can compete for a Super Bowl right now, and could still draft a quarterback in this year’s draft, having him learn under Brady for the next two years. I may not believe that Tom Brady is better than Dak Prescott at this point in his career, but this is the Dallas Cowboys and Jerry Jones, and we know how much Jerry likes to make a splash. In the end, the fairy tale stories that we want to hear about for content don’t always come to fruition, and because of that I think Dak remains with the Cowboys on what could be a franchise tag to begin with, ultimately leading to a multi-year deal with an annual salary all around 32 to 34 million dollars.

Prediction: Dallas Cowboys: Franchise Tag to multi-year contract

Tom Brady (43)

Rumors have been swirling and picking up steam over the past couple of weeks regarding the Tom Brady and his divorce from the New England Patriots. It is probably split 50/50 in the industry and amongst fans about whether or not Brady actually does leave New England. I’m going to put my side on the 50% that does have Tom Brady playing in a different uniform in 2020 .  While that very much may not be the case, and this is all just a bunch of smoke, it is obviously a lot more fun to talk about Tom Brady in another uniform. The hardest part for me is trying to predict where exactly, or what uniform that is. By now, you have already heard the teams as potential fits including the Los Angeles Chargers, Las Vegas Raiders, Chicago Bears, Tampa Bay Buccaneers, Tennessee Titans, and even the New York Giants.  If it’s about winning another Superbowl none of the aforementioned teams get me excited, although the Tennessee Titans and Chicago Bears would have the best shot at that. However, I don’t necessarily believe that a fresh start with a new team and winning a Superbowl is what will drive Brady to another city. At 43 years old, and wanting to play at least another two years, Brady could be looking at what’s next. The next chapter in his life after football. I have narrowed my destinations for Brady down to three; Indianapolis Colts, Las Vegas Raiders, and the Tampa Bay Buccaneers. taking a closer look at each three destinations, the Raiders present Brady with a city and a platform to continue the Brady brand after his playing days are over. However in a similar fashion to that of New England, the weapons around him aren’t that great, and his chance of winning, especially in that division does not bode well for his legacy. The Indianapolis Colts, have the luxury of playing indoors in a more quiet City, and they do have some good, young, talented wide receivers at his disposal. As of now the Colts have the second highest cap space which enables them to go out and get even more weapons on both the offensive and defensive side of the ball to surround Brady and make him feel comfortable. It doesn’t hurt that they already have one of the best offensive lines in football. Now,  there has been a lot of speculation and buzz regarding the Indianapolis Colts and free-agent Philip Rivers. I do think that Rivers and the Colts are a very nice match, however I also think that Rivers and the next team that I was going to speak about regarding Brady, the Tampa Bay Buccaneers, are also a very nice match. This could be an interchangeable situation, where if Rivers ends up in Indianapolis, then I feel Brady ends up in Tampa Bay and vice versa. From the coaching and offensive side of the ball, the Tampa Bay Buccaneers give Tom Brady exactly what he needs; multiple playmakers on offense. The Bucks are right behind the Colts as far as the most salary cap space this season and have enough to sign Brady as well as a dynamic running back, while still upgrading on the defensive side of the ball. With the Atlanta Falcons struggling, the Carolina Panthers in a transition year, and the New Orleans Saints also with an aging quarterback and limited cap space, adding Brady and some other pieces could put the Bucs atop that division. 

Prediction: 

Tampa Bay Buccaneers: 2 year 62M 

Phillip Rivers 

As mentioned above I feel Tom Brady and Philip Rivers and their destinations for 2020 are interchangeable. One of them will end up in Indianapolis and the other will end up in Tampa Bay. Ever since the report came out shortly after the regular season that Rivers was not going to be back with the Chargers, I immediately thought the best fit for him was going to be with the Buccaneers and, and I still believe that. However it is very hard to ignore the reports from some very respected industry minds at the NFL combine, that have been saying that Rivers and Indianapolis could very well be real thing. Chances are that a Brady destination is going to take a little longer than some of the other free agent quarterbacks, and teams like the Colts may want to move a little more quickly, and therefore not wait for Tom Brady to make a decision. I mentioned the offensive line of the Colts when talking about Brady, and that line is just as important when we are talking about a quarterback like Philip Rivers. The indoor part of it might even be a bigger factor for somebody like Rivers and not Brady. 

Prediction: Indianapolis Colts: 2 years, 48M, 30M guaranteed.

Ryan Tannehill (31)

Photo Credit: USA Today

Tannehill revitalized his career in 2019, as well as the Titans season. Tennessee was 2-4 through their first six games, despite a defense that was allowing only 15.3 points per game. Tannehill was named the starter for the remaining 10 games; a ten game stretch in which he led the team to a 7-3 record and a spot in the playoffs.The Titans didn’t ask Tannehill to do too much, but regardless of how many times they threw the ball, an average of 30 pass attempts a game (tied fewest in the league), the results of putting points on the board and getting wins is what’s important. From weeks 7-17, the Titans averaged 30.4 points a game, almost double the production from weeks 1-6 under Mariota. The new Titans offense, along with the smothering defense, had the Titans in the AFC Championship game, where they eventually lost to Kansas City Chiefs. Tannehill did enough to warrant himself a nice payday in his free agent year, and I don’t see why the team would fix something that isn’t broken. 

Prediction: Tennessee Titans: 3 Years, 75M, 55M guaranteed

Jameis Winston (26)

Still only 26 years old, Winston has shown flashes of why he was the 1st overall pick in the 2015 draft…He has also shown why he shouldn’t have been the 1st overall pick. We already predicted Tom Brady going to the Buccaneers, so I doubt the team would use so much cap space on two quarterbacks, and Winston shouldn’t settle on being a backup to Brady. Winston is coming off of a season in which he threw for over 5,000 yards on a whopping 626 pass attempts, and 33 touchdowns. That’s the good part. His 33 interceptions and 12 fumbles is the bad. The Tampa defense isn’t good enough, and most likely still won’t be good enough in 2020 to handle that many turnovers and get involved in shoot-outs. Hence the Brady signing. Winston is still a starting caliber wide receiver in my opinion, and he will get the opportunity again in 2020. What happens after the upcoming season is anyone’s guess, as based on my prediction, the team that signs him will also be drafting one early in the draft. 

Prediction: Los Angeles Chargers: 1 year, 24M, 24M guaranteed.

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Mariota is a tricky one to predict because we don’t know if someone is going to take a chance on him as a starter, or will he have to settle for a backup role. Some reports have the Patriots as a potential destination if Brady departs. That does make some sense, but I think he gets signed to a relatively “high” backup contract and will be able to compete for a starting opportunity. 

Prediction: Chicago Bears: 1 year, 10M, 10M guaranteed, Bonuses could reach total to 14M

Teddy Bridgewater (27)

Hasn’t been able to land a starting job since coming back from his gruesome leg injury that almost cost him his life. He played well in the five starts he had for the Saints this past season, going 5-0, with a 9:2 TD to INT ratio. Bridewater can finally get his chance…especially if that quarterback we keep talking about doesn’t return. 

Prediction: New England Patriots: 2 Years 22M, 18M guaranteed