The MLB season will soon reach a critical deadline: Teams and their arbitration-eligible players have until Friday, January 13 to submit pay numbers for 2023. This isn’t the most exciting deadline in terms of the hot stove, but it is serious business since the great majority of players will have signed contracts for 2023 by then.

The unofficial beginning of extension season is marked by the filing deadline. One such deal was completed this month when Rafael Devers and the Red Sox agreed to a hefty 11-year, $331 million contract to keep him from becoming a free agent following the season.

Despite the exceptional circumstances caused by the lockout, a number of players, including Emmanuel Clase, Ke’Bryan Hayes, Ryan McMahon, and Matt Olson, signed long-term extensions between the conclusion of the lockout and the start of the season. Even though Devers’ deal was the first of the year, other massive contracts will almost definitely be signed before the 2023 season starts. Check out the top three MLB players who could get long-term deals.

3. Brandon Woodruff

Although the Brewers have a number of contract contenders, including Willy Adames and Corbin Burnes, Woodruff seems to be the most likely to sign a long-term agreement that is within the team’s budget constraints. It’s safe to assume that Adames is salivating over the shortstop contracts that were signed this offseason, and Burnes has roughly two years on Woodruff in age.

Since 2015, Milwaukee’s Opening Day payroll has never been better than the 17th, therefore the team must carefully use their resources. Of course, Woodruff is terrific, and the Brewers wouldn’t settle for less even if he has a better chance of signing a cheap long-term deal than Adames or Burnes.

2. Logan Webb

One option for the San Francisco Giants to fix things is to extend the contract of the popular domestic star, Logan Webb. Certainly not all, but a few. Webb is a local person who grew up just about two hours outside of the Bay Area, and negotiations for a contract have already started.

With just Mitch Haniger signed until 2025, the Giants have relatively little long-term payroll commitment, giving them a lot of flexibility. They have enough cap space to re-sign Webb and make another go at major free players in the summer after failing to get any of the big fish this time around. Webb is, bar none, the greatest player on the club, so signing him to a long-term deal is smart business.

1. Kyle Tucker

Though not every player on the team receives an extension (recent free agents Gerrit Cole, Carlos Correa, and George Springer are examples), the Astros make sure to keep hold of their most valuable assets. Long-term contracts have recently been given to players like Jose Altuve, Alex Bregman, and Lance McCullers Jr. Yordan Alvarez inked a six-year, $115 million contract in June of last year. Three years from now in 2023, Tucker will be eligible for free agency, and by that time he is expected to have made close to $6 million.