ORLANDO, Fla. — The New York Yankees lost two key bullpen arms this offseason. Now Brian Cashman is hunting for replacements.
Two names from the National League have emerged as primary targets. One is a free agent coming off a career year. The other is an All-Star closer who could be available via trade.
Brad Keller and Trevor Megill both dominated NL hitters in 2025. Both could be wearing pinstripes by Opening Day. Here is what makes each arm so intriguing for the Yankees.
Yankees bullpen needs are urgent
The Yankees watched Devin Williams sign with the Mets on a three-year, $51 million deal. Luke Weaver remains unsigned and appears unlikely to return. That leaves significant holes in the late innings.
David Bednar and Camilo Doval are in place after arriving at the trade deadline. Tim Hill is back after the team exercised his $3 million club option. But the Yankees need more.
Joel Sherman of The New York Post reported Monday at the Winter Meetings that the Yankees have shown interest in both Keller and Megill. Each would address different needs in different ways.
Keller’s stunning transformation with the Cubs
Nobody expected Brad Keller to become one of baseball’s best relievers in 2025. He signed a minor league deal with the Cubs last January worth just $1.5 million. He was coming off a dismal 5.44 ERA split between the White Sox and Red Sox in 2024.
Then everything changed. Keller posted a 2.07 ERA in 69.2 innings across 68 appearances for Chicago. He struck out 75 batters against just 22 walks. He recorded 25 holds and three saves while only blowing three leads all season.
The 30-year-old right-hander was dominant in the second half. He allowed just one earned run while striking out 35 hitters across 27.2 innings from late July through August. He kept rolling in October, tossing 5.2 innings of one-run ball in the playoffs with two saves and a hold.
The key to Keller’s breakout was simple. He added 3 mph to his fastball and became more effective with his sinker and sweeper. His ground ball rate climbed to 56.1%. His strikeout rate jumped to 27.2%, a massive increase from his time as a starter with the Royals.
Sherman reports the Yankees are interested in Keller primarily as a reliever. However, they could use him in the rotation early in the year while Gerrit Cole and Carlos Rodon recover from surgery.
MLB Trade Rumors projected Keller to land a three-year, $36 million deal on the open market.
Megill brings proven closing experience
Trevor Megill is a different kind of target. The Yankees would need to make a trade with Milwaukee to acquire him.
Sherman reported that the Brewers are receiving calls from multiple teams about Megill, including both the Yankees and Mets. Milwaukee has fielded inquiries but has not indicated they must move him.
The 32-year-old right-hander posted a 2.49 ERA in 50 appearances for the Brewers in 2025. He converted 30 of 36 save opportunities while striking out 60 batters in 47 innings. He earned his first All-Star selection.
Over the past two seasons, Megill has been dominant. He owns 51 saves with a 2.60 ERA, 1.07 WHIP, and 10.6 strikeouts per nine innings across 98 appearances. His fastball touches 100 mph. His curveball is devastating.
A flexor strain sidelined Megill for most of September. But he returned for the playoffs and looked sharp, allowing one run on three hits with five strikeouts in four innings. Over three postseasons in Milwaukee, he has allowed just one run in 7.1 innings with a 12-to-1 strikeout-to-walk ratio.
The Brewers’ familiar pipeline to the Bronx
Acquiring Megill would mark another trip to the Milwaukee well for Cashman. The Yankees traded for Devin Williams last December. Before that, they acquired other arms from the Brewers organization over the years.
The irony is not lost on anyone. Williams struggled in his first season in New York, posting a career-worst 4.79 ERA before recovering late. Now he is gone to the Mets. If Cashman trades for Megill, he would be replacing one former Brewers closer with another.
Milwaukee has a pattern. They trade star closers and replace them internally. They dealt Josh Hader. Williams stepped up. They traded Williams. Megill became an All-Star. Now the cycle could repeat with Abner Uribe waiting in the wings.
Megill is projected to earn $4.2 million in arbitration for 2026. He has two years of team control remaining. That makes him valuable to contenders seeking bullpen help without long-term commitments.
Cost considerations for each target
Keller and Megill present different financial calculations for the Yankees.
Keller is a free agent. The Yankees would pay only dollars, no prospects. But a projected $36 million deal over three years would count against the luxury tax. The Yankees are currently less than $1 million from the third tier of the competitive balance tax. Going over would increase their tax rate and drop their top 2027 draft pick by ten spots.
Megill would cost prospects but carry a smaller payroll hit. His $4.2 million projected salary is far more manageable. For teams deep in luxury tax territory like the Yankees, trading for controllable relievers often makes more financial sense than signing free agents.
The Brewers would likely demand significant prospect capital. They just finished with the best record in the National League and have no pressure to sell. But their payroll hit a franchise-record $135.5 million after Brandon Woodruff accepted his qualifying offer. Budget concerns could open the door.
What the Yankees gain from either option
Both Keller and Megill would provide immediate bullpen upgrades.
Keller offers flexibility. He can pitch high-leverage innings out of the bullpen. He can also start games if the Yankees need rotation help early in the season. That versatility has real value given the injury situations with Cole, Rodon, and Clarke Schmidt.
Megill is a proven closer. He has the stuff to dominate the ninth inning and the postseason track record to back it up. He would slot right into the role Williams was supposed to fill.
The Yankees could pursue both. Keller as a free agent signing. Megill as a trade acquisition. That would give them multiple late-inning weapons to support Bednar and Doval.
The Winter Meetings continue through Thursday. Cashman has made clear that bullpen help is a priority. These two NL breakout arms sit at the top of his list.
What do you think? Leave your comment below.
IF CLARKE SCHMIDT MAKES IT BACK IN 2026, HE WILL BE A RELIEVER.
If they were looking for bullpen help why didn’t they make a offer to Edwin Diaz?