The Toronto Blue Jays are expected to maintain their aggressive approach during the upcoming Major League Baseball winter meetings in Orlando. Following a successful run to the World Series, the team has made significant moves in the off-season, including signing right-hander Dylan Cease to a seven-year, $210 million deal. They also secured Cody Ponce with a three-year, $30 million contract and retained Shane Bieber through a player option. This winter is notable as traditionally wealthy teams like the Los Angeles Dodgers and New York Yankees are not dominating the free-agent market. Instead, the Blue Jays are stepping up to make high-profile acquisitions. As the winter meetings commence, the Blue Jays have several key needs to address, particularly in the infield and outfield. They are looking for a powerful bat to enhance their lineup, with potential upgrades at second base, third base, shortstop, or in the outfield. If they acquire an outfielder such as Kyle Tucker, they could shift Addison Barger to third base, Ernie Clement to second, and Andrés Giménez to shortstop. Alternatively, if Bo Bichette returns, Barger would move to right field, allowing Bichette and Giménez to play together in the middle infield. General Manager Ross Atkins has indicated that the team is open to adding a new closer, with several prominent names still available in free agency, including Edwin Diaz, Robert Suárez, and Pete Fairbanks. The Blue Jays have been in contact with the agents of these players. In addition to free agency, the Blue Jays may explore trade opportunities. Last year, they acquired Giménez from the Cleveland Guardians, and they could pursue similar deals this year. Outfielder Joey Loperfido is a likely trade candidate due to limited playing time. The team may also consider trading prospects like Arjun Nimmala, JoJo Parker, and Johnny King, as well as Barger. They are also looking to offload José Berríos and his $70 million contract. If the Guardians are willing to trade outfielder Steven Kwan or if the Arizona Diamondbacks make second baseman Ketel Marte available, the Blue Jays are expected to show interest. Currently, the Blue Jays project a payroll of $267 million for the upcoming season, ranking second in the majors. Their competitive tax balance payroll is $282.5 million, with teams incurring a tax when exceeding $244 million. The team faces various penalties for payroll overages, and with several roster needs, they are likely to increase their spending in the coming weeks. The winter meetings will feature several key events. On Monday, a news conference will introduce the successful candidates from the Classic Baseball Era committee for the Hall of Fame. On Tuesday, representatives from countries participating in the next World Baseball Classic will be available to the media, and Blue Jays manager John Schneider will address reporters for the first time since the World Series. The Blue Jays will also hold a news conference to introduce Cease, with Atkins and Cease's agent, Scott Boras, expected to attend. On Wednesday, the Rule 5 Draft will take place, where the Blue Jays hold the 27th pick but are unlikely to make a selection. Players chosen in this draft must remain on the 26-man roster for the entire season, with a minimum of 90 days on the active list, or be returned to their original team. Triple-A outfielder Yohendrick Pinango, ranked as the team's No. 7 prospect, may be at risk of being selected.