For the first time in his illustrious career, future Hall of Fame quarterback Tom Brady will likely become a free agent. Brady has spent his last 19 seasons in New England, winning six Super Bowls with the Patriots in the process. But now, it is looking more and more possible that Brady will allow himself to be courted by other teams. He is set to become a free agent March 18th, and the future of the 42-year-old quarterback is the most intriguing storyline entering the NFL offseason. The big question is – where will Tom Brady play in 2020?

In his most recent mailbag, Pro Football Network Insider Tony Pauline reported that during the Senior Bowl, two teams that were mentioned the most in the Brady sweepstakes were the Miami Dolphins and Las Vegas Raiders.

“The two teams mentioned throughout Senior Bowl week were the Miami Dolphins and Las Vegas Raiders. Miami seems to be the team continually in the conversation and I can tell you this:

1) Word is that Tom Brady’s wife prefers Miami.

2) The rumor for months now is Brady will ultimately buy an ownership interest in the Miami Dolphins. If it happens, it won’t be for a few years, but the rumblings over Brady taking an ownership position in the franchise have been getting louder.”

Adding to what Pauline reported, PFN Insider Ben Allbright refuted media reports that Brady and his wife Gisele were visiting private schools in Tennessee on Thursday. Allbright is also reporting that there is another team in the mix – the Los Angeles Chargers (more on that below).

But why has Brady now – after 19 seasons – decided to test the open market? According to reports by Gary Tanguay of NBC Sports Boston, Brady is “embarrassed” by how his salary with the Patriots pales in comparison to what many of his quarterback colleagues earn. There are currently 13 NFL quarterbacks who earn more on an annual basis than Brady. However, it is worth noting that Brady had openly decided to take team-friendly contracts over the years to be better surrounded by high-caliber players.

With the six-time Super Bowl champion set to test the open market for the first time, look for more teams to jump into the mix as the offseason progresses. In the interim though, we can look at some of the teams who appear to be in the mix for Brady’s services.

Could Tom Brady be headed to the Chargers?

Now that they have decided to move on from Philip Rivers, Allbright reports that both Brady and the Chargers are open to discussions. According to Allbright, Brady likes the idea of heading to the Chargers with the talent that they have. Also, their offensive coordinator Shane Steichen currently runs the Erhardt-Perkins offense, similar to what is run in New England. Brady’s only concern is with the offensive line talent that the Chargers currently have. Nonetheless, Allbright says that both sides will be interested in the offseason.

For the first time in 16 seasons, a world without Rivers is about to begin for the Los Angeles Chargers. As of right now, their current quarterback depth chart consists of Tyrod Taylor and Easton Stick – neither of which the organization is completely comfortable handing the reigns over to. We have been reporting that the Chargers will likely be looking to add a QB in the 2020 NFL Draft. Both Tony Pauline and Ben Allbright believe that that quarterback could be Oregon’s Justin Herbert.

If Herbert is added to the current quarterback roster, bringing in a veteran like Tom Brady to help mentor him would make quite a bit of sense. If you look at their current cap situation, they are projected to have just under 49 million available for the 2020 season. If the team decides to move on from RB Melvin Gordon, they will likely have enough cap space to acquire Brady’s services.

Another reason that Brady to the Chargers could make sense is his long time connection with the city. Brady grew up in L.A. and has spent numerous offseasons training in the city. Jason La Canfora of CBS Sports reported something similar.

“Brady trains often in Southern California and has family in that state,” La Canfora wrote. “He has held spring passing camps there, his business partner and trainer lives there (Alex Guerrero) as does his throwing specialist (Tom House). Brady has also become increasingly engrossed in Hollywood, with a second career looming perhaps in large-scale productions.”

Chargers’ popularity has struggled since they moved from San Diego to Los Angeles. Over the last season, when the team underperformed and finished with a 5-11 record, numerous home games were packed with away team fans. It has been difficult for an organization with such promise. With a new 70,000 seat stadium being introduced next season, bringing in a top-level, ultra-popular player like Brady would surely help fill the empty seats at Chargers games. His connection to the city could be the best bargaining chip the team will have.

Could Brady lead the Las Vegas Raiders to a successful first season? 

The Oakland Raiders will officially – and symbolically – complete their move to Las Vegas when the 2020 season opens. Bringing in a massively successful quarterback to lead the team would make quite the splash. But how realistic is a Brady and Jon Gruden team?

The rumors started when Brady was spotted talking with Raiders’ owner Mark Davis at UFC 246 in Vegas earlier this month. UFC owner Dana White added fuel to the fire by saying the Brady-Raiders marriage talk is real.

Those reports were then followed up with the news that Brady had potentially purchased property in Las Vegas. But before Raiders fans get too excited, it’s worth noting that Brady owns property all over the country. A purchase could be completely innocuous and totally unrelated to his career.

The Raiders finished the 2019 season with another losing record at 7-9. It is believed that Brady would like to go to a team that is not too far away from contending and have the pieces in place to succeed. The Raiders are currently rebuilding and are no sure thing to compete this season. However, they do have some pieces in place. They have a stout running game, led by Offensive Rookie of the Year favorite Josh Jacobs, plus some young talent in Hunter Renfrow and Darren Waller.

Of course, the Raiders have a quarterback at the moment. Derek Carr is entering the third year of a five-year, $125 million contract that made him the richest player in NFL history when it was agreed upon three years ago. However, since the arrival of Gruden, there have been rumblings that the head coach wants to upgrade the position.

In addition to the talent already on the roster, the Raiders are projected to have about $70 million in salary cap room this offseason. That would likely be enough to be able to fit Brady into the picture. The reality is that getting rid of Carr for a soon to be 43-year-old quarterback wouldn’t make much sense. But when you look at the business side of the spectrum, especially with the Raiders wanting to make a splash in their new home, it makes sense.

If the Raiders decide to draft a quarterback early this year, Brady could help mentor that player until he decides to retire. With two first-round picks (12, 19), getting one of the top quarterback talents would be possible.

Will Tom Brady sign with the Miami Dolphins? 

One bombshell that Pauline dropped in his mailbag was that Brady may be looking to invest as a minority owner of the Miami Dolphins. The connection between Brady and Miami is evident, but does that mean he wants to be under center come 2020?

Off the field, there are numerous reasons this would make sense. The Dolphins have a lot of cap space available, nice weather for most of the year, his wife would like to call Miami home, and there are a lot of wealthy, health-conscious people in the area. If you don’t take Miami’s roster into consideration, it could be the perfect place for an older Brady to play his final years and retire while growing his TB12 brand.

Brady also has a connection with a number of members of the coaching staff in Miami. Obviously, Brady and Dolphins head coach Brian Flores spent years together in New England. He also had a connection with former offensive coordinator Chad O’Shea but O’Shea was replaced with veteran play-caller Chan Gailey this offseason. O’Shea was a former Patriots assistant, and he ran the same offense Brady has played in throughout his NFL career.

The problem? Brady wants to play for a team that is close to winning. The Dolphins are still rebuilding. They are one of the least talented teams in the league, which was evident when they didn’t have a single player selected for the Pro Bowl — not even as an alternate. They are adding pieces, and with a wealth of draft picks this year, they will likely be able to fill some of their holes. However, Brady might not be willing to wait that long.

Are the Tennesse Titans really an option for Tom Brady? 

The Tennessee Titans are wrapping up a Cinderella season, where they shocked many and made it to the AFC Championship game. They ultimately came up short against the Kansas City Chiefs. Riding on the back of a record-breaking stretch by Derrick Henry, they were one game away from the Super Bowl.

When head coach Mike Vrabel decided to make the switch from Marcus Mariota to Ryan Tannehill, no one expected Tannehill to lead the team to a 7-3 record. So, if Tannehill could do that with the weapons this team has, imagine what Brady could do. ESPN’s Steven A. Smith believes that Tennessee would be the best fit for the free agent.

“I’m here to tell you something right now, it’s Tennessee,” he said. “The Tennessee Titans, the team that lost in the AFC Championship Game last year, is where Tom Brady should go.”

There are surprisingly quite a bit of New England connections to the Titans as head coach Vrabel isn’t the only former Patriot in Nashville. In addition to Vrabel, ex-Patriots director of college scouting Jon Robinson is the Titans’ general manager. New England’s 2009 third-round pick Tyrone McKenzie is inside linebackers coach and the roster features former Patriots running back Dion Lewis, wide receiver Cody Hollister, guard Jamil Douglas and cornerbacks Logan Ryan and Malcolm Butler.

However, would the Titans be willing to pay Brady the amount required to bring him in? Both Tannehill and Henry are free agents this offseason, and Henry will likely require a massive payday to stay in Nashville. They might not have the cap space to bring Brady in after paying their star running back.

Will Brady return to play for the New England Patriots?

According to multiple sportsbooks, the New England Patriots are still the team that is favored to sign Brady, even with his cryptic tweets and willingness to test free agency.

Brady has long made it known that he wants to play until he’s 45, a feat that is only a few years away from becoming a reality. Brady and Patriots head coach, Bill Belichick, have formed perhaps the most dominant quarterback/head coach duo in the history of the NFL.

The idea that Brady might walk away from that on the heels of a Wildcard round loss to the Titans and Tannehill is unlikely. Brady is a winner, and he wants to go out on top. Erasing the memory of that Titans loss with another New England Super Bowl is probably what could entice him to stay.

However, if the Patriots organization is to keep Brady, they will need to do a few things first. To begin, they will have to open the checkbook and give Brady whatever amount of money he wants. After the years of sacrifice and team-friendly deals, it is unlikely Brady will take anything but top dollar.

They will also need to add to his supporting staff. The Patriots offense struggled for most of the year, and Brady lacked the weapons that he needs to be successful. The franchise is projected to have approximately $49 million in cap space this offseason. After paying Brady, they will need to use what is left to bring in some big-name talent. If they do both of these things, a return to New England isn’t as far off as some believe.

The 2020 free agency window is anticipated to be one of the most exciting ones to date, with Brady, Drew Brees, Philip Rivers, and Teddy Bridgewater slated to enter free agency this offseason. There will likely be a number of teams with new leaders in 2020. Will Brady be one of those new leaders? Or will he end up getting the payday he wants in New England? As they say, time will tell.

For more CFB/NFL news and rumors, follow Allbright on Twitter: @AllbrightNFL along with Pauline: @TonyPauline and Pro Football Network: @PFN365.