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After 13 consecutive years of making the postseason, a run that included six American League pennants and four World Series titles, 2008 marked the first season in some time that the Yankees failed to play for keeps in October. It was still an 89-win campaign, but given their historic run, it was a disappointing way to end their tenure in that iteration of Yankee Stadium.

2009 was a new chapter for a the franchise, with a fancy new stadium to call home. Clearly, they had intentions of making some noise that year, and began that process with a historically active offseason. Many of their important moves will be covered in this series, but the first free agent domino to fall, which helped fuel the Yankees to their 27th World Series win, was veteran pitcher A.J. Burnett.

A.J. Burnett
Signing Date: December 13, 2008
Contract: Five years, $82.5 million

Allan James Burnett, born and raised in Little Rock, Arkansas, was drafted by the Mets in the 8th round of the 1995 draft. Prior to breaking into the big leagues, the 6-foot-4 right-hander was sent off to the Marlins, in exchange primarily for Al Leiter. A season later, Burnett would be making his Major League debut for Florida.

This began a seven-season run with the Marlins, which was largely successful for Burnett and his club. His time in South Florida was not without his highlights — in May of 2001, Burnett tossed a no-hitter against the Padres, and later that season made blooper reels with a warm-up pitch that “accidentally” hit a promotional pickup truck driving behind the plate.

The following season featured some of Burnett’s finest work on the mound, as he managed a 3.30 ERA in over 200 innings of work, while topping 200 strikeouts for the first time in his career. He missed most of the ‘03 season after undergoing Tommy John Surgery, and had to watch from the dugout as his squad went on to beat the Yankees in the World Series that year. He would return, however, posting two more solid seasons with the Fish, throwing as hard as ever post-procedure.

Burnett would test free agency for the first time following the 2005 season, and landed in Toronto, where he would continue his solid work as a hard-throwing strikeout-heavy big league starter. In 2008, the righty pitched a career-high 221.1 innings and was the AL’s premier strikeout artist, amassing 231 of them. For the 31-year-old, it was among the ideal ways to enter free agency once again.

Burnett’s strong performance in Toronto, his free agency (via opt out), and the aforementioned Yankee desire to build a contender after a disappointing ‘08 season seemed to make for a good match. Hank Steinbrenner had made the Yankees’ interest in the veteran righty clear, and the club unsurprisingly inked Burnett to a five-year deal worth over $80 million.

A.J. Burnett’s time in New York started out quite well. Across 33 starts in 2009, he topped 200 innings once again, and despite a league-leading 97 walks, the hard-throwing righty racked up just shy of 200 Ks, and managed a respectable 4.04 ERA (114 ERA+). In terms of bWAR, it was actually Burnett’s most valuable season in the Majors – not a bad way to ring in the new contract.

On top of the solid regular season, Burnett made his mark in the Yankees’ successful postseason run as well. He started five games in the playoffs, including two in each of the Championship Series against the Angels, and the World Series against the Phillies. This stretch was highlighted by his performance in Game 2 of the Fall Classic, when he pitched seven innings, allowing just one run on four hits, while striking out nine Phillies to help New York quickly even the series in wake of a bumpy Game 1.

He wasn’t the Yankees premier starter that year, as they had signed CC Sabathia later in the offseason to fill that role, but Burnett, along with Sabathia and Andy Pettitte, formed a more-than-suitable front of the rotation — one that was clearly good enough to help win them a ring.

Unfortunately, the ‘09 season would be the best of Burnett in pinstripes, as he struggled to maintain nearly the same level of success over the following seasons. He continued to go out there every fifth day, making 33 and 32 starts respectively, between 2010-11, but with much diminished performance. In 2010, over 186.2 innings, the righty sported a much less palatable 5.26 ERA (82 ERA+), with a lower strikeout rate that he hadn’t seen since his early days as a starter. He struggled in the postseason too, allowing five runs in his lone start that October.

In his age-34 season, 2011, both he and the Yankees likely hoped for a rebound on the mound. Unfortunately, the story was much the same for the veteran. His 83 ERA+ marked little improvement, as more concerns started to pile up, as he also allowed a career-high 31 home runs in his third season with the Yankees. Burnett had become more inconsistent than anything following 2009, and despite still having good stuff on the mound, the Yankees appeared to have had enough after a second straight disappointment in 2011. He at least had enough to conjure up one last bit of playoff magic in the much-memed “I Believe in A.J.” start, Game 4 of the ALDS when the Yankees’ backs were up against the wall. Burnett was the benefactor of greatdefense in center from Curtis Granderson, but he still tossed 5.2 innings of one-run ball for the win. (The Yankees were eliminated the next day.)

After shopping Burnett’s services, the Yanks eventually struck a deal with the Pirates, sending the veteran starter to Pittsburgh for the final two years of his contract. The Yankees would eat more than half of the remaining money owed to him.

Burnett would pitch the next two seasons as a member of the Pirates (and eventually finish there), and despite beginning the 2012 season with a freak injury, would play some of his best baseball as well. Between 2012-13, in nearly 400 innings of work, Burnett posted a 3.41 ERA and impressive 3.17 FIP, figures he hadn’t touched since his days with the Marlins. On top of that, the 2013 season saw him remarkably post a career-best 26.1 percent strikeout rate at the age of 36.

Burnett made a brief and unsuccessful detour to the Phillies for the 2014 season, before returning to Pittsburgh to even more success. In 2015, his final season, Burnett posted a career-low ERA, walked fewer batters than he had in a decade, and for the first time, at 38-years-old, made an All-Star team.

Although his time in New York was shorter than what he or the organization envisioned when he signed his five-year deal, it would be hard to call his contract a failure. His success was mostly contained to just one season, but when that one season is spent as a critical part of a championship team, other warts can reasonably be overlooked.

His time in pinstripes was brief, in the span of a 17-year career in the Major Leagues, a very good one at that, but A.J. Burnett did his part when it mattered for the Yankees, making his signing all the more significant.

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See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.

Fourth in the series. Today we look at the Cubs’recently-acquired backup DH/First Baseman.

Tyler Austin is a 34-year-old journeyman, drafted by the Yankees in the third round of the 2010 MLB Draft. His lifetime 0.9 bWAR is inflated by his reasonable 2018-2019 seasons.

After 2019, he journeyed to NPB, where he did well for six years, and also played for the US team during the last Olympics. The Cubs seem to be banking on some transferable improvements from those experiences. Austin right now is penciled in as a backup to first baseman Michael Busch and DH Moises Ballesteros. It’s unclear if he’ll open the season on the major-league roster, given the Cubs’ needed bench improvement, but if he provides a big RH bat off the bench, he very well could break camp bound for Wrigley.

Most projections have him in that spot, and slashing something like .240/.315/.430, with 10-ish homers and 30-ish RBI in 200+ plate appearances. Austin has good power and isn’t a butcher at first, but that and DH are his only spots, and the Cubs need positional versatility. He’ll have to hit his way to Chicago.

The Pittsburgh Pirates are hoping to break their drought of over a decade of not playing in the postseason in 2026.

They certainly helped their chances with some free agency and trades this offseason. That’s why MLB.com reporter Mark Feinsand listed the Pirates as one of the winners of the offseason.

“The Pirates haven’t played into October since 2015. Early in the offseason, word was that Pittsburgh was ready to spend some money this winter, though nobody expected them to dive into the top end of the free-agent market,” Feinsand wrote.

“Still, the Pirates hadn’t signed a free agent to a multi-year deal since Ivan Nova in December 2016, and no free-agent hitter had received a multi-year contract since John Jaso a year before that. That changed this winter when the Pirates signed All-Star Ryan O’Hearn to a two-year, $29 million deal, while the Pirates also acquired two-time All-Star Brandon Lowe. The additions of O’Hearn and Lowe should help a lineup that ranked last in the NL in runs scored in 2025, while Mason Montgomery (acquired in the Lowe trade) and Gregory Soto (one year, $7.75 million free-agent deal) should help fortify the bullpen.”

The other teams listed as winners included the Los Angeles Dodgers, Toronto Blue Jays, New York Mets, Chicago Cubs, Baltimore Orioles, and Chicago White Sox.

While the Pirates moves don’t guarantee much, it gives them the opportunity to be better than they were a year ago. That is enough to bring some optimism and life into the clubhouse, which could be exactly what the Pirates need in order to break this long curse of mediocre baseball.

BD community, do you feel as if the Pirates had a winning offseason? Let your voice be heard by chiming off in the comments section below.

Sure, it’s practically February, but the White Sox promised to be players in free agency.

All it took was getting Luis Robert Jr’s $20 million salary off the books for the front office to suddenly get ‘very active’ at exploring roster upgrades.

Of course, needing to dump Robert’s salary just to have operating income to acquire talent has led to a new round of criticism toward the franchise. Much of the criticism challenges the notion that aggressive teams like the Dodgers are the “downfall” of baseball when teams like the White Sox need to give away salaried players just to attempt to be competitive for the coming season.

It is hard to avoid getting frustrated with the team’s frugal ways, considering roster upgrades still could have been made even with Robert’s bloated salary included in the payroll. The club had $87 million committed to the roster per FanGraphs’ RosterResource before Robert was traded to the New York Mets.

However, we must stop getting upset over or surprised by owner Jerry Reinsdorf’s failure to reallocate revenue into player payroll. It is what it is. The hope is that this current group of talented young players, along with the promising prospects on the way, will allow the franchise to succeed despite the frugal owner.

It has happened before (although the owner eventually finds a way to ruin everything).

At least, Getz immediately reinvested Robert’s salary by signing reliever Seranthony Domínguez to a two-year, $20 million contract. He is going to be counted on to be the team’s closer, even though he has sporadic experience in that area. At the very least, he is a solid, high-leverage reliever. The bullpen desperately needed an upgrade in that area.

This club could still use a veteran outfielder to provide some cover in case Luisangel Acuña or Brooks Baldwin fail to take off with the runway they will be given. A left-handed bat off the bench would be nice to have. Another starting pitcher would be a welcome addition. That would allow the recently-signed veteran Sean Newcomb to be moved to the bullpen, where he has been more effective.

If another innings-eater is not added, then adding another high-leverage left-handed reliever must be a priority. I am not sure I trust Tyler Gilbert or Brandon Eisert to get outs in tight situations, considering they were not very good at it in 2025.

The prevalent thinking is that the White Sox should not shun the idea of acquiring any talent because of the team’s three-straight 100-loss seasons.

That was true when it came to last offseason. The club was coming off the worst season in the 162-game era. When you only win 41 games, any player available was better than what the team had.

Things changed last season when a young, talented core of players emerged in the process of losing “only” 102 games. The franchise now has young talent. It just needs that core to continue to ascend while mixing in additional prospects who are showing promise in the minors. While those prospects are still marinating, effective veterans to bridge the gap must be added (although it seems like the general manager prefers discarded talent that was once highly thought of).

I am actually fine with Getz sticking to his plan of finding former highly-regarded prospects who have not panned out yet due to a lack of consistent playing time. It cannot hurt to search for the next Brent Rooker.

If one does not exist, then Getz should be pursuing veterans where there is a good chance of still squeezing out the last good ounces of baseball those players have left.

Getz must also avoid upsetting a clubhouse that is building tremendous chemistry.

All that considered, there are three moves he must avoid making before Spring Training kicks off.

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Do not trade for Nick Castellanos
There is no official rumor linking the White Sox to Castellanos. Two brothers in the White Sox content world have floated the idea. It was based on USA Today’s Bob Nightengale’s suggestion that the Philadelphia Phillies would have to dump Castellanos’ salary to sign Bo Bichette.

The Phillies will likely still try to trade Castellanos, even after failing to acquire Bichette. They added Adolis García in the offseason. The relationship between Castellanos and the organization is strained. Castellanos was benched for a game because of a tirade he had toward manager Rob Thomson over getting pulled for defensive purposes. The relationship continued to deteriorate from there.

The logic behind the White Sox adding Castellanos is that they have the payroll flexibility, so long as the Phillies eat a significant chunk of his $20 million salary. Chicago could use a veteran corner outfielder, and the cost to acquire him will likely be a lowly-regarded prospect.

However, the White Sox must avoid considering adding the combustible and declining veteran. Nightengale pointed out that any team that acquires him must be ready to play him every day, or there will be problems: “If you bring Castellanos in, you’d better play him every day, or he is going to be upset and could cause you a disturbance in the clubhouse, which is what would happen in Philadelphia.”

Castellanos’ production decline no longer makes him an everyday player, at least not in the field. He is terrible defensively, with a career -90 defensive runs saved in right and -77 outs above average per FanGraphs. The White Sox already have one terrible defensive corner outfielder in Andrew Benintendi. They should not be adding another.

The Pale Hose also must keep the DH spot as flexible as possible to make sure young players such as Kyle Teel, Edgar Quero, and Lenyn Sosa get regular at-bats.

That means no regular playing time for Castellanos, and opens up a clubhouse cancer to wreak havoc. This young, impressionable roster cannot afford to be exposed to Castellanos’ temper tantrums over a lack of playing time. They need a solid, steady veteran to show the kids how to go about the business, not someone who pouts when he is asked to take a reduced role.

Speaking of younger players, Baldwin provided very similar production last season:

Out slugged by Brooks Baldwin. #Nohttps://t.co/J2GbcugkoTpic.twitter.com/IM6F0h0Sbq

— BZ (@BezBeyondThePen) January 15, 2026

I would rather give Baldwin a runway to see if he can reach the Ben Zobrist ceiling that the front office believes he has, rather than seeing if Castellanos bounces back.

Signing Michael Conforto over Harrison Bader
It appears the plan for the outfield is to give Acuña a runway to prove he can still live up to his highly-regarded prospect status in center field. The Mets at least made sure he got some reps there in the minors, so here is hoping the conversion to the outfield goes better than it did for Andrew Vaughn or Gavin Sheets.

Baldwin appears slated to be the starting right fielder, with Everson Pereira in reserve. Then you’ve still got Benintendi’s atrocious defense in left.

If Derek Hill or Jarred Kelenic make the roster out of Spring Training, they can at least replace Benintendi late in the game for defensive purposes. That will still leave Baldwin or Acuña needing to play late as they still adjust to tracking fly balls.

That makes me incredibly uncomfortable, along with only having Benintendi as the only true veteran.

That is why adding another proven veteran to the outfield is a must. Signing Harrison Bader to a short-term contract would have been the ideal solution. It would have lessened the sting of losing Robert’s elite defense. He would still provide that glove to rob some doubles and singles as LRJ did. Also, Bader would have provided a huge upgrade over “Louie” Robert at the plate against right-handed pitching.

The problem with adding Bader is that he could get in the way of the front office wanting to give Acuña that runway it so desperately wants to provide. And cost — Bader signed virtually the same deal as Domínguez, getting two years and $20.5 million from the Giants on Monday — would have been another issue.

Now, the White Sox reportedly are interested in signing Michael Conforto. That rumor came out when Getz was working with a tighter budget, but knowing the White Sox it still could be true with a few more dollars to work with; never underestimate this organization’s ability to save money and bet on a veteran having a “bounce-back” season.

Rolling the dice on a proven veteran like Conforto producing better numbers than a .199/.305/.333 slash line in 2025 could make sense. Getz has a bit more cash to work with and should have used that money on Bader, who can play better defense in center and right while still having some good baseball left in him. Even with both players to choose from, it would not be a shock if Getz went with Conforto.

Bringing back Mike Clevinger as an organizational depth pitcher
Signing Mike Clevinger when no other big-league club will has become an annual tradition on the South Side, one that has become a terrible look for the Pale Hose.

First, you got his off-the-field issues with past domestic violence allegations. This organization already has enough public relations problems. Continuing to bring back this shady character only exacerbates them.

The other reason it becomes an annual embarrassment is that 29 other big-league teams won’t touch him with a minor-league deal and non-roster invite to camp. He has been available on the open market four times since the White Sox brought him to 35th and Shields. All four times, no other team showed interest.

He was placed on waivers after the trade deadline in 2023, when he was pitching well. No contender claimed him despite the pitcher being on the way to a 3.2 bWAR season. No team signed him the following offseason despite the impressive metrics. Unlike the White Sox, the rest of the league saw him for what he is — injury-prone, and a public relations nightmare.

That did not stop the organization from bringing Clevinger back in 2024, where he could not throw strikes and suffered a season-ending injury. Once again, no team touched him in the offseason except the White Sox, who thought he could be the team’s closer in 2025.

They were asking a guy coming off a major surgery to throw harder, and it went as badly as expected. Yet, the organization kept him at Triple-A after designating him for assignment.

Hopefully, that was his last run with the club. The team has to get out of the Clevinger business because the business has been bad for years now.

Twenty-nine other teams will not touch him. Hopefully, the White Sox finally become No. 30.

The Mets have four prospects ranked on ESPN's new top 100 list ahead of the 2026 MLB season, with all of those players within the top 31.

ESPN's list is the latest to show the Mets still having one of the best farm systems in baseball despite recently trading Jett Williams and Brandon Sproat to the Brewers in the deal that brought Freddy Peralta and Tobias Myers to New York.

The Mets had four prospects on The Athletic's new list that was released on Monday.

Here's how the Mets on the new ESPN list stack up:

No. 13: RHP Nolan McLean
No. 15: OF Carson Benge
No. 28: OF A.J. Ewing
No. 31: RHP Jonah Tong

McLean dazzled in 48.0 innings over eight starts during his big league debut last season, posting a 2.06 ERA and 1.04 WHIP while striking out 57 batters. He is expected to slot near the top of the 2026 rotation, perhaps right behind Peralta. 

Benge, who ended the 2025 season with Triple-A Syracuse, will compete for a spot on the Opening Day roster -- and could be the starting left fielder if he makes it, with Luis Robert Jr. slated to be the starting center fielder andJuan Soto entrenched in right field. 

The other two prospects on the list will likely open 2026 in the minors. 

Tong showed flashes during his first taste of the majors in 2025, but his arsenal can use some refining. The expectation is that he'll begin the season with Triple-A Syracuse, where he made just two starts before his promotion to the bigs late last season. 

As far as Ewing, he had a breakout season in 2025, slashing .315/.401/.429 (.830 OPS) across three levels, ending with Double-A Binghamton. The speedy Ewing smacked 10 triples and 26 doubles while swiping 70 bases. 

Williams and Sproat ranked No. 32 and No. 73, respectively.