The MLB Winter Meetings are about to start, and the race to acquire baseball’s top free agent is on. Teams from the top markets are preparing to offer Gerrit Cole the most lucrative contract for any pitcher in league history.

Multiple reports indicate that both the New York Yankees and Los Angeles Angels are all-in when it comes to their attempts to sign Cole. According to ESPN’s Jeff Passan, that potentially means engaging in a bidding war that could include offers of much more than $250 million.

The Los Angeles Dodgers are in the mix, as well, potentially making this a three-team race. It’s looking highly unlikely that the Houston Astros will match what the other contenders are prepared to offer the right-hander. Cole led the Astros to Game 7 of the 2019 World Series.

The Yankees, Angels and Dodgers all met with Cole this week ahead of the Winter Meetings, which will take place in San Diego from Dec. 8-12.

The seven-year, $217 million contract that David Price signed with the Boston Red Sox ahead of the 2016 season still hasn’t been topped by any pitcher in terms of overall value. Zack Greinke’s $34.4 million average annual salary is the highest mark of all time.

A seven-year, $245 million contract would break both records. Cole could earn significantly more money than that with at least two teams that have plenty of money to spend making him their top priority this offseason. 

New York needs to upgrade its rotation after falling short in the 2019 ALCS. The Yankees have been eliminated in either the ALDS or ALCS in three straight years. It’s been 10 years since the Yankees last won a title, marking the franchise’s third-longest drought since New York won its first World Series in 1923.

The Angels haven’t sniffed World Series contention, despite having the sport’s best player on their roster. Mike Trout has three AL MVP awards, four second-place MVP finishes and no playoff series victories in his eight full seasons with the Angels. L.A. had its fourth straight losing season in 2019.

The Dodgers were defeated in both the 2017 and 2018 World Series before blowing a lead at home in Game 5 of the 2019 NLDS. Hyun-Jin Ryu is a free agent after leading the team with a 2.32 ERA and a 1.01 WHIP this past season.

The Dodgers might be more likely to sign Stephen Strasburg, who will command a lesser contract than Cole. The reigning NL West champions are also in contention to sign Anthony Rendon.

There have been rumors that Cole, a California-native, prefers to return to the West Coast.  That idea has lost some steam in the wake of his meeting with the Yankees.

Cole went 20-5 with Houston in 2019, leading the AL with a 2.50 ERA and 326 strikeouts in 212.1 innings. The 29-year-old had a 1.72 ERA in 36.2 playoff innings.

Cole has a career 3.22 ERA with more than 200 innings pitched in three of the last four seasons.