The Yankees got Aaron Judge back -- now here's what they need to do to actually get better this winter Dylan Buell/Getty Images 7:00 AM ET David SchoenfieldESPN Senior Writer Close Covers MLB for ESPN.com Former deputy editor of Page 2 Been with ESPN.com since 1995 Now that the New York Yankees are bringing back Aaron Judge after the two sides sweated out a negotiation that concluded with the reigning American League MVP agreeing to a nine-year, $360 million contract, what's next? This is a franchise that has had plenty of success in recent seasons: 99 wins and an AL East title in 2022, six consecutive trips to the postseason and three trips to the AL Championship Series in that span. The Yankees, however, don't merely play for success: The expectation is to win a World Series, and the Yankees haven't even been to one since their last championship in 2009. Their three latest appearances in the ALCS all ended in defeat to the Astros and New York hit a combined .198 in them -- including .162 with just nine runs in a four-game sweep in 2022. Re-signing Judge was the necessary first step to dethroning the Astros, but it is bringing back someone the Yankees already had. What else should they do to get better? The simple answer: Spend more money. Let's take a little step back first and explain why the current Yankees aren't quite the Evil Empire Yankees of the late 1990s and 2000s. The Yankees have enjoyed a 100-year advantage over the rest of the sport, ever since they purchased Babe Ruth from the Red Sox in 1920: financial resources. They haven't always been smarter, they haven't always been better at developing players, they haven't always made the best trades. They've always had more money to spend on players. Editor's Picks Aaron Judge is back in the Bronx! But did the Yankees overpay? 20h Bradford Doolittle 2 Related Over the past decade, however, Hal Steinbrenner decided to squander that advantage, operating with a profit-first mindset. From 2000 to 2012, the Yankees led the majors in payroll every season. Since then, they've led just once, in 2020. Yes, they've signed plenty of big free agents along the way. They are now the first team to employ three $300 million players as Judge joins Giancarlo Stanton and Gerrit Cole . They still run high payrolls -- third in 2022 -- and will go over the luxury tax in most years, although they've also been careful in recent years to reset their tax by going under the threshold from time to time, as they did in 2021. Steinbrenner, no doubt, would like to remind everyone that the Yankees have paid $348 million in tax penalties since 2002, more than double any other team (the Dodgers are the only other club over $100 million in penalties). As a quick example of how the Yankees used to completely eclipse the rest of the league in player salaries, we can compare their payroll with the average of the other nine teams in the top 10 in payroll. That ratio peaked in 2005 when the Yankees had a payroll of $208.3 million, more than twice the $95.7 million average of the other teams in the top 10. From 2000 to 2012, the Yankees' payroll averaged 64% higher than the rest of the top 10. Since 2013, that average has been just 16% -- and the team's payroll was less than the average in 2018 and 2021. That's fine if the farm system is pumping out inexpensive talent, but that hasn't been the case. Of the 18 Yankees to produce at least 1.0 WAR in 2022, the only homegrown players were Judge (debuted in 2016), Luis Severino (debuted in 2015) and rookie reliever Ron Marinaccio . Two others, Gleyber Torres and Michael King , were acquired as minor leaguers and have spent their entire major league careers in pinstripes. But it has been a long time since Judge and Severino broke out in 2017 and Torres in 2018. Keep up with the MLB offseason Need to know what to make of the moves that shape the offseason? We've got you covered. That means general manager Brian Cashman has had to import a lot of expensive talent. Judge, Cole and Stanton will make a combined $108 million in 2023. That trio will be making over $100 million combined through 2027. When three players are taking up that much payroll, it forces the hand of the organization: (1) play more young players; or (2) ramp up the payroll. Regarding that latter point: The Yankees' current $266 million estimated luxury tax payroll (via Roster Resource) is already higher than the Yankees have ever gone ($259 million last season). Unless Steinbrenner is ready to break out from his operating philosophy of the past decade and suddenly go all Steve Cohen on us, the next moves aren't necessarily as simple as (A) sign Carlos Rodon ; (B) sign Brandon Nimmo (or even Andrew Benintendi ); and (C) sign a couple of relievers. So let's map out a few ideas: 1. Sign RHP Kodai Senga I'd love to say just go old-school Yankees and sign Rodon, the best remaining free agent pitcher out there, but given the contracts given to ex-Yankees starter Jameson Taillon (four years, $68 million) and Taijuan Walker (four years, $72 million), Rodon's reported asking price of a six-year contract suddenly doesn't seem so outrageous. Still, six years at $30 million brings the total to $180 million and that may be too rich for the Yankees given the commitments we've just discussed. They do need to replace Taillon, however, so let's go down to the next-best starter on the list, the hard-throwing Senga. He throws in the upper 90s with a wipeout split-fingered offering and in Japan posted a 1.89 ERA in 2022 and 2.67 in 2021. He's entering his age-30 season and looks to be in the prime of his career. Dan Szymborski's ZiPS projection forecasts a 3.54 ERA and 2.9 WAR over 22 starts and 140 innings, but I think there's more upside than that given the track record of top-of-the-line Japanese pitchers who have come to the majors. He's reportedly interested in a "big market" and, hey, New York is a big market! Kiley McDaniel's original estimate of five years/$72 million is probably a little low given the way this market has developed and the high regard MLB teams have for Senga, so let's estimate six years/$112 million ($18.7 million average annual value). 2. Trade for Pirates OF Bryan Reynolds Reynolds has asked the Pirates for a trade. The Pirates don't want to trade him and the last thing a team should do is give in to a player's trade demands since that can lead to rash decisions. That said, if a player doesn't want to be in your organization do you really want him around -- even if Reynolds is regarded as a high-character guy? It's rare for an MLB player to go all NBA like this, especially since Reynolds is more good player than star, but the Pirates will listen to trade offers. The good news for the Yankees: Reynolds will make "just" $6.75 million in 2023, with two arbitration years after that. His salary is cheaper than Benintendi or Nimmo would cost, he is more durable than either and I would take his next three seasons over the next three seasons of those two -- certainly, Benintendi. The best of Aaron Judge Check out all our latest coverage and favorite stories from the slugger's historic season. The road to 62 » | Magical night of 60 » Free agency: $375M? » | 7 places he could land » Where this season ranks all-time » Of course, he'll cost some major prospects in return, with the Pirates no doubt starting trade demands with Anthony Volpe or Jasson Dominguez. I don't know if the Yankees want to do that, but Cashman certainly hasn't been shy about trading away prospects in the past -- although it's been a while since he had one as highly rated as those two. Here's the key: The Yankees offense scored 123 runs more than the average AL team in 2022. Judge himself was about 80 runs better than the average hitter. Except it's not realistic to expect Judge to be 80 runs better again, so you have to build in some regression to his numbers. In his stellar rookie season in 2017 he was 58 runs above average; in 2021, he was 37. If Judge declines 30 to 40 runs, the Yankees will need to pick up some offense elsewhere (especially given how the offense performed in the second half). Left field is a good position to upgrade as the Yankees were just 23rd in the majors in OPS there. 3. Trade Josh Donaldson . OK, let me rephrase that: Give away Josh Donaldson, and eat some of his salary in the process. Donaldson will make $21.75 million in 2023 with a $6 million buyout of his 2024 salary. That's $27.75 million -- and the Yankees might have to eat all but $10 million or so. Given Donaldson's age and poor performance in the playoffs, it's time to move on, especially since the Yankees have a glut of infielders: Donaldson, Isiah Kiner-Falefa , Gleyber Torres, DJ LeMahieu , Oswald Peraza , Oswaldo Cabrera and Volpe on the way. Ranking the top 50 MLB free agents How much will Judge, Correa, Turner and others get paid this winter? Kiley McDaniel breaks down this year's free agent class. Top 50 2022-23 free agents » Trade Donaldson, move LeMahieu to third base, start the season with Peraza at shortstop and Torres at second base, and heck, let's trade Kiner-Falefa and his $6 million salary as well. Whichever teams don't end up with one of the big free agent shortstops may need somebody and Kiner-Falefa is excess for the Yankees at this point. The Donaldson/Kiner-Falefa trades clear $16 million and leave Cabrera in the backup role as a super utility player with Volpe in Triple-A (assuming none of those players is used to acquire Reynolds!). 4. Sign another reliever. The Yankees signed Tommy Kahnle to a two-year deal after he looked really good for the Dodgers in his first extended time in the majors since 2019, but he has been able to reach 40 innings only three times in his career. It's a good gamble with a high payoff if he's healthy. Given some of the injury concerns of last year's pen -- by playoff time, Aaron Boone was scrambling to find enough healthy relievers -- more depth is needed. How about a reunion with former Yankee David Robertson ? He had a 2.40 ERA last season with the Cubs and Phillies and held batters to a .173 average, still generating a ton of swing-and-miss with that curveball. They can probably get him on a one-year/$8 million or two-year/$16 million deal. OK, so we've added: Senga at $18.7 million. Reynolds at $6.75 million. Robertson at $8 million. And we've subtracted Donaldson and Kiner-Falefa at a combined $16 million. That comes out to $17.45 in additional payroll, pushing the 2023 level up to an estimated $284 million. Yes, it's no fun always talking about payroll like this, but this is the way the baseball world works with everything fitting into each team's specific budget jigsaw puzzle. The Yankees can easily afford a $284 million payroll even if that makes the Steinbrenner family a little squeamish. We've added a switch-hitter in Reynolds to at least give the Yankees another left-handed batter to counter all the right-handed pitching on the Astros. We've upgraded offensively at shortstop with Peraza. We've improved the contact in October with LeMahieu instead of Donaldson. We've added a hard-throwing No. 2 or No. 3 starter to go with Cole, Severino, Nestor Cortes , Frankie Montas and Domingo German . And the guy who hit 62 home runs is back. That's an excellent team. Can it beat the Astros?