With free agency underway, the offseason is going to pick up steam. What are the big questions facing all 30 teams?

Here's a look at the AL East, which features two teams that won 96 or more games in 2019, two clubs that posted 95 or more losses this year ... and, right in the middle, the 2018 World Series champs.

Team-by-team offseason previews: NL East | NL Central | NL West

New York Yankees: Will the Yankees land Gerrit Cole or Stephen Strasburg?

2019 record: 103-59
2020 World Series odds: 5-1

The Yankees' biggest offseason storyline will be how general manager Brian Cashman will improve his starting rotation, which on the first day of the GM meetings he stated would be a team priority. The marquee names on the free-agent market, Gerrit Cole and Stephen Strasburg, are potential targets, but certainly not the only ones.

"Obviously, starting pitching is always something that we want to try to continue to look at and shore up," Cashman said. "There are some exciting opportunities that exist in the marketplace via trade as well as free agency. Of course, we're going to talk to Strasburg; we'll talk to Cole. We'll talk to the higher-end guys, clearly, and have conversations, and we'll also talk about some surprise guys, I'm sure."

The Yankees also will have to address how many of their own free agents they want to keep, and most importantly, how much they want to spend doing so. Cashman has specified that there is no ownership mandate on a maximum payroll, but it's doubtful a team with more than $210 million in salary commitments for 2020 would be able to work out deals with a Cole or a Strasburg, and also bring back Brett Gardner, Didi Gregorius and/or Dellin Betances.

Beyond that, the 2019 Yankees overcame a barrage of injuries to win 103 games and their first AL East title since 2012. But the "Next Man Up" mentality and performance that went along with it is unlikely to be duplicated. The Yankees will likely have to address their injury prevention and treatment protocols in order to avoid setting yet another MLB record for most injured players in a single season. -- Marly Rivera

Tampa Bay Rays: Can the Rays stay creative to keep thriving in the East?

2019 record: 96-66
2020 World Series odds: 30-1

The Rays have never been short of good, outside-the-box ideas. After another successful season of bullpenning, Tampa Bay has enough strong starters on its roster, among Charlie Morton, Blake Snell, Tyler Glasnow, Yonny Chirinos and Ryan Yarbrough, to field a full rotation -- if the Rays want to. In 2019, they found a lot of success from their bullpen, between Emilio Pagan's lockdown year and strong performances from Nick Anderson and Oliver Drake, and they'll likely keep looking for more diamonds in the rough, given relievers are a notoriously fickle group when it comes to year-to-year consistency (looking at you, Jose Alvarado). Two-way top prospect Brendan McKay could become an interesting factor for Tampa Bay as well, after making his debut both on the mound and at the plate.

General manager Erik Neander hopes to prioritize adding offense to a lineup that finished the season with 769 runs, seventh in the American League. Catcher Travis d'Arnaud hits the open market following his best season, hitting .263/.323/.459 in 92 games. While they weigh bringing back d'Arnaud, the Rays, who had the lowest payroll in the majors in 2019, will look to upgrade at designated hitter, with veteran names such as Edwin Encarnacion and Howie Kendrick being tossed around as solutions. Foundational players such as Glasnow, Austin Meadows and Snell remain under team control, with Tampa Bay facing $73.8 million in 2020 salary commitments heading into the offseason. Neander will explore every possible option to make marginal improvements to an already strong team facing financial restrictions. -- Joon Lee

Boston Red Sox: How will a new front office balance Mookie Betts and the budget?

2019 record: 84-78
2020 World Series odds: 10-1

Boston enters the offseason with a new chief baseball officer in Chaim Bloom and an offseason already filled to the brim with rumors about what the team will do with superstar Mookie Betts as he enters his contract year -- but the questions don't stop there. Bloom faces the challenge of getting the team's payroll under the luxury tax threshold -- balancing big-time salaries, from Betts to designated hitter J.D. Martinez to starters Chris Sale, David Price and Nathan Eovaldi -- while a World Series-worthy roster remains the goal.

Bloom's decisions over the next few months will not only shape Boston's direction for next year, but for the foreseeable future. If Boston hopes to keep both Betts and Martinez for 2020, the organization will likely need to trade some of its bigger contract commitments, requiring the creativity that made Bloom a rising front-office star with the Rays. -- Lee

Toronto Blue Jays: Can they build a winning team around the kids?

2019 record: 67-95
2020 World Series odds: 75-1

In 2019, the Toronto Blue Jays let the kids play. In 2020, will they be able to find anyone who can pitch? That is the overriding question this offseason for the position-rich Jays, who saw not only Vladimir Guerrero Jr. make his much-hyped MLB debut last season, but also Cavan Biggio and Bo Bichette step into the limelight.

That impressive collection of controllable talent could go to waste in the coming years without a vastly improved pitching staff.

Despite team president and CEO Mark Shapiro telling reporters the team will need to "be aggressive on every level of the free-agent starting pitcher landscape," the Blue Jays are unlikely to open the wallet for big-ticket items, but should be involved in acquiring second-tier veteran options like Gio Gonzalez, Julio Teheran or Michael Pineda. A middle-of-the-road farm system will make it difficult to trade for a top-tier arm.

Nonetheless, in a top-heavy division such as the AL East, a 95-loss team faces a Herculean task in breaking through by limiting itself to smaller-scale moves, particularly given the fact that Shapiro and general manager Ross Atkins have uncertain futures beyond the 2020 season. -- Rivera

Baltimore Orioles: How long will they be at this level of awful?

2019 record: 54-108
2020 World Series odds: 1,000-1

"Improving" from 115 losses in 2018 to 108 last year shouldn't be mistaken for the start of a turnaround, because as bad as the Orioles have been, GM Mike Elias' total rebuild doesn't really have an upward trajectory yet. While the farm system gets restocked, the team will still be scrounging for talent to field a quasi-competitive club in 2020.

That's because the current group doesn't have much room for growth. You'd be hard-pressed to name a current Oriole who might be a major contributor to the next good ballclub in Baltimore -- unlike, say, the Astros, who at least had Jose Altuve during their bad patch of three consecutive 100-loss seasons.

Although Trey Mancini had an excellent year, it was his age-27 season, and he's under club control for just three more years. Will the O's be ready by then? Or will they have traded him? Middle infielder Jonathan Villar might be Elias' best bargaining chip, but he's just one year from free agency. Even their top rookie of 2019, lefty John Means, is just a couple of months younger than nominal top starter Dylan Bundy. -- Christina Kahrl