Three Things to Watch for at the Winter Meetings

Where will Aaron Judge sign? Plus, notes on Trea Turner, the Kolten Wong trade and Gaylord Perry.

Editors’ Note, Dec. 2 at 9:35 p.m. ET: This story has been updated to include the news of Jacob deGrom’s signing with the Rangers.

The last time the Winter Meetings were held in person, in 2019, we saw three of the top free agents (Stephen Strasburg, Gerrit Cole and Anthony Rendon) sign contracts for a combined $814 million. Who cares if only one of those deals have worked out? It was exhilarating to experience the three star players coming off the board in chaotic succession at the signature event of the offseason.

With this year’s Winter Meetings set to begin Sunday, let’s take a look at some of the top story lines heading into what could be another blockbuster week in baseball.

Aaron Judge sweepstakes

Judge is expected to sign with either the Yankees or the Giants :: Erick W. Rasco/Sports Illustrated

Over the last eight months, we’ve been hearing all about how Judge bet on himself when he turned down a seven-year, $213.5 million extension from the Yankees just before Opening Day. Now, after putting together perhaps the greatest contract year in baseball history, Judge could cash out with a record-breaking deal sometime within the next week. ESPN’s Jeff Passan reported Wednesday that the Yankees recently offered Judge an eight-year, $300 million deal, though they are willing to go up if another team offers him more.

The Giants appear to be New York’s most serious contender for Judge, who is from Linden, Calif., and grew up rooting for San Francisco. Additionally, the Giants are one of the few teams with the financial resources to outbid the Yankees. “From a financial standpoint, there's nobody that would be out of our capability,” Giants president of baseball operation Farhan Zaidi said last month at the GM Meetings in Las Vegas, though he didn’t mention Judge specifically.

Another factor here is a team’s ability to spend to improve the team around Judge, who has said throughout his career that anything short of winning a World Series is a failure. This is his first and maybe his only chance to pick his team; joining an organization that has a legitimate chance at success, by his definition, every single year is among his top priorities.

“I want to be in a winning culture and be on a team that's committed to winning,” Judge said, according to MLB.com’s Bryan Hoch. “Not only for the remainder of my playing career, but I want a legacy to live on with any organization. First and foremost is just about being in a winning culture and a winning future.”

Yes, it’s true that the Yankees have won more World Series (27) than any other franchise, but their last title came in 2009, when Judge was a senior at Linden High School. The Giants have won three World Series since then. This isn’t to say the Yankees aren’t committed to winning—only the Dodgers have won more regular-season games since the start of ’10—just that the Bronx is no longer the obvious destination for a free agent looking to win.

As things stand, Judge would be more likely to win the World Series if he re-signs with New York than if he goes to San Francisco. That said, it’s worth noting the Giants have far more financial flexibility to sign other top free agents this season. Their estimated luxury tax payroll is about $143 million, or $90 million below the first threshold. Say they were to sign Judge for eight years and $320 million ($40 million AAV) after a bidding war, they’d still have $50 million to spend before having to pay the 20% tax penalty on whatever they spend above $233 million.

The Yankees, meanwhile, have a projected luxury tax payroll of $222 million, meaning they not only would blow past the first threshold if they sign Judge, but they’d also need to go over the second one, at $253 million, which comes with a 12% surcharge. Moreover, they exceeded the tax threshold last year, so as repeat offenders, their tax penalty would be 30%. Owner Hal Steinbrenner reportedly has spoken with Judge on a few occasions since the Yankees were eliminated from the postseason and told Judge that New York has enough money set aside to sign him to a record-breaking deal and upgrade the roster with additional moves, per Hoch.

The Winter Meetings could be the Turner-ing point of the offseason.

Over the last seven seasons, Trea Turner leads the majors with 228 stolen bases :: Gary A. Vasquez/USA TODAY Sports

Yes, that was a dreadful pun. No, I will not apologize for it. Hopefully, it won’t be as bad as whatever puns Scott Boras makes when he speaks to reporters in San Diego. Either way, there will be a lot of buzz at the Winter Meetings about the big four free-agent shortstops: Carlos Correa, Xander Bogaerts, Dansby Swanson and, yes, Trea Turner, who is the most intriguing one to me.

Few players can match Turner’s combination of average, power and speed, especially at his position. He’s one of two active shortstops with at least 100 career home runs and 200 stolen bases. The other, Jean Segura, has played nearly 500 more games than Turner and hasn’t played shortstop consistently since 2020.

Turner: 124 HR, 230 SB, 849 G
Segura: 107 HR, 205 SB, 1,328 G

I’m really curious to see how many bases Turner will steal next year with the new bigger bags and rule limiting the number of pickoff attempts a pitcher can make per plate appearance. He stole a career-high 46 in 2017 and 43 in ’18. Could he swipe 60?

Pitcher payday

Justin Verlander has an estimated market value of more than $45 million per year, according to Spotrac. If he gets that much, he would be the highest paid player ever based on AAV.

The Astros, Yankees, Mets and Dodgers all are reportedly in the mix for Verlander, though where he signs could come down to the length of the contract. Houston doesn’t want to give Verlander, who turns 40 in February, a three-year deal, per Jon Heyman of the New York Post.

Two hours after this story was first published, the Rangers announced they had signed Jacob deGrom to a five-year deal. The deal is for $185 million and includes a conditional sixth-year option, which could bring the total value to $222 million, according to Passan.

After missing out on re-signing deGrom, the Mets could pivot to Verlander, who would rejoin his former Tigers teammate Max Scherzer atop the rotation. New York could also look to replace deGrom, 34, with free agent Carlos Rodón or in a trade for Brewers righthander Corbin Burnes.

Have any questions or comments for our team? Send a note to mlb@si.com.

1. THE OPENER

“The first thing Brandon Woodruff noticed about Brent Suter was his water bottle.

“It wasn’t the reusable bottle itself, exactly, that stood out to him. It was Suter’s commitment to it. The two pitchers met as minor leaguers at Brewers spring training in 2015, and Woodruff noticed that Suter seemed to bring the bottle with him everywhere, from clubhouse to ballfield to dugout and back—almost more like a security blanket than a drinking receptacle.”

That’s how Emma Baccellieri begins her excellent feature from yesterday about reliever Brent Suter, now with the Rockies, who is one of the few professional athletes who speaks regularly about trying to combat climate change.

The Secret of Baseball’s ‘Treehugger’ Pitcher: Fast Showers, Reusable Water Bottles … and Don’t Be Weird by Emma Baccellieri

2. ICYMI

A lot has happened since the last newsletter. Let’s get you caught up on some of our best stories:

The Best Plan B’s If Aaron Judge Signs Elsewhere by Nick Selbe
Here are the best fallback options for the teams that fall short in the sweepstakes for the AL MVP.

Who We’d Vote for the HOF If We Were on the Veterans Committee by SI MLB Staff
Let’s pretend we’re one of the 16 members voting in Sunday’s Contemporary Baseball Era election.

José Abreu’s Signing Helps Astros Approach Evil Empire Status by Nick Selbe
Replacing MLB’s worst first baseman with the 2020 American League MVP gives Houston a good shot at becoming a true dynasty.

Where Have All the Star Center Fielders Gone? by Tom Verducci
Things are looking bleak at this once-glamorous position. What happened? Is there hope for a revival?

3. WORTH NOTING from Matt Martell

Kolten Wong hit a career-high 15 home runs this season :: Jeff Hanisch/USA TODAY Sports

We’ve got some trade news this Friday afternoon! The Mariners are acquiring second baseman Kolten Wong from the Brewers in exchange for outfielder Jesse Winker and infielder Abraham Toro, according to The Athletic’s Ken Rosenthal.

Wong, who is in the final year of his contract and will make $10 million next year, is coming off a rather uncharacteristic season. Known for his elite defense, Wong was the opposite in 2022. He was worth –9 outs above average, per Baseball Savant, the second worst mark for a second baseman in the league. Wong attributed his surprising defensive woes to injuries. He spent 20 days on the IL in June with a calf strain.

Seattle is expecting Wong’s glove to return to normal and his improvements on offense to continue. In 134 games last season, he batted .251 with 15 home runs and a 118 OPS+, meaning he was 18% above league average.

This is the second major trade Milwaukee has made this offseason, after it sent right fielder Hunter Renfroe to the Angels for three pitchers on Nov. 22. Winker, who hit 24 home runs and was an All-Star with the Reds in 2021, will replace Renfroe while Toro should see playing time at both second and third base.

4. TRIVIA from Matt Martell

Previous Question: Paul Goldschmidt is the sixth Cardinals first baseman to win the MVP award. Who are the other five?

Answer: Albert Pujols (2005, ’08, ’09), Keith Hernandez (1979), Orlando Cepeda (’67), Stan Musial (’46) and Jim Bottomley (’28). Musial also won MVP in ’43 and ’48, but he was primarily an outfielder in those two seasons.

Question: Gaylord Perry is one of two pitchers with at least 3,000 career strikeouts and 300 complete games. Who is the other?

5. THE CLOSER from Emma Baccellieri

RIP, Gaylord Perry, who died this week at the age of 84. To look back, here is Jack McCallum’s 1982 cover story on Perry’s 300th win, including a description of his celebratory t-shirt. (“300 WINS IS NOTHING TO SPIT AT”...!) And here is a 1974 feature headlined “Forkballer of the Year,” with one quote from a scout that captures part of his legacy: “He proved to me that you don't have to be brilliant to be a great pitcher. It works against you sometimes. Gaylord just has a natural talent for pitching a baseball, and he can throw the ball wherever the catcher tells him to."

That’s all from us today. We’ll be back in your inbox tomorrow. In the meantime, share this newsletter with your friends and family, and tell them to sign up at SI.com/newsletters. If you have any questions or comments, shoot us an email at mlb@si.com.