Each MLB Team's Biggest Obstacle to Having a Successful Offseason

We are still in the early stages of the MLB offseason, and things won't kick into gear until all 30 teams convene at next month's winter meetings.

In the meantime, each team should be working to avoid certain pitfalls in their pursuit of a successful offseason.

Whether it's a thin farm system, a tight payroll situation, a diminished trade chip or something else entirely, each organization has at least one significant obstacle standing in the way of offseason success.

Off we go.

Baltimore Orioles: Inability to land quality pitching

The Orioles finished the 2019 season with an MLB-worst 5.59 ERA, with starter John Means (131 ERA+) and relievers Mychal Givens (104 ERA+) and Miguel Castro (101 ERA+) as the only above-average regular contributors.

The pitching staff needs an entire overhaul for this team to approach respectability, and attracting even second- and third-tier arms will be a challenge.

Boston Red Sox: Payroll slashing the No. 1 focus

The No. 1 goal for the Red Sox this offseason appears to be getting below the luxury tax threshold. After J.D. Martinez opted into the final three years of his contract, which includes a $23.75 million salary for 2020, that will be no easy feat.

Whether it's a trade of Mookie Betts or several other smaller moves to shed salary, the front office could wind up selling players below full market value for the sake of the organization's long-term outlook. Framing the offseason as a successful one will be tricky.

New York Yankees: Too much focus on Gerrit Cole

If the Yankees go all-in on signing Gerrit Cole and fail, it could mean missing out on other arms that could greatly help the team's starting rotation.

With a report coming out last week that Cole likely won't sign until January, according to Andy Martino of SNY.tv, putting all their eggs in that basket and whiffing on signing him could mean the Yankees miss out on upgrading the rotation entirely.

Tampa Bay Rays: Financial limitations

Money is always going to be the No. 1 hurdle in Tampa Bay.

Despite wrapping up the 2019 season with the lowest payroll in baseball at just over $64 million, the Rays won 96 games and took the Houston Astros to five games in the ALDS. The two-year, $30 million deal given to Charlie Morton last offseason likely once again represents the peak of what they will be willing to do this winter.

Toronto Blue Jays: A diminished market for Ken Giles

The Blue Jays missed a golden opportunity to flip closer Ken Giles for a significant return last summer before right elbow inflammation landed him on the injured list prior to the trade deadline.

The 29-year-old is entering his final year of arbitration eligibility, and his market has been quiet so far, according to Scott Mitchell of TSN Sports. His value will only diminish as he moves closer to free agency, so failing to find a suitable trade this offseason would represent another missed chance.

Chicago White Sox: Manny Machado 2.0

The White Sox pulled out all the stops in their pursuit of Manny Machado last offseason and walked away disappointed, despite offering a contract that general manager Rick Hahn deemed "superior" to his eventual Padres deal while talking with reporters.

On the heels of seven straight losing seasons and with a playoff drought that stretches back to 2008, it's fair to wonder whether the South Siders will be able to attract any marquee free agents before they first prove relevant.

Cleveland Indians: Unclear direction

Are the Indians going to shop Francisco Lindor? What about Corey Kluber? Or are they going to try to contend once again after a 93-win season that saw them fall just short of a fourth straight playoff appearance?

These important questions need to be answered, and answered decisively. Otherwise, the Indians risk occupying the dreaded gray area between contention and rebuilding, which would have significant consequences to both their short- and long-term outlook.

Detroit Tigers: A diminished market for Matthew Boyd

Left-hander Matthew Body had a 3.94 ERA and 1.13 WHIP with 178 strikeouts in 132.1 innings over 22 starts when the trade deadline came and went. While he was a popular name on the trade market, no contender was willing to meet an exorbitant asking price.

The 28-year-old then went on to struggle to a 6.11 ERA over his final 10 starts, lowering his stock in the process. With team control through the 2022 season, he's still a valuable asset, but the rebuilding Tigers might have missed their chance to sell high and that could become clear this winter.

Kansas City Royals: Unwillingness to fully commit to rebuilding

The Royals continue to cling tightly to top trade chip Whit Merrifield, despite the fact that he's 30 years old and might not be part of their next contender. They were "not inclined" to eat salary to facilitate trades of Ian Kennedy and Danny Duffy last summer. They have focused on MLB readiness rather than upside when targeting other teams' prospects.

It's the approach of a team on the fringe of contention, not one saddled with back-to-back 100-loss seasons. There's no light at the end of the tunnel for this organization right now, and an unwillingness to go all-in on rebuilding is the reason.

Minnesota Twins: Not enough attention paid to the bullpen

Even with Jake Odorizzi accepting his qualifying offer, the Twins still potentially have three spots to fill in the starting rotation, depending on how they feel about Randy Dobnak, Devin Smeltzer and top prospect Brusdar Graterol.

As such, the rotation figures to be the focal point of the offseason, but the bullpen cannot simply be ignored. The trio of Taylor Rogers, Trevor May and Tyler Duffey was rock-solid last year, but this team needs at least one more proven late-inning arm for the bullpen to be a strength.

Houston Astros: Failing to properly replace Gerrit Cole

In theory, the Astros have enough in-house talent to let both Gerrit Cole and Wade Miley walk in free agency and still have a viable starting rotation.

Justin Verlander and Zack Greinke will be back at the top, Brad Peacock can start, Lance McCullers Jr. will return at some point, and young pitchers like Jose Urquidy, Josh James and Framber Valdez have shown enough to provide plenty of reason for optimism. This team is built to win now, though, and failing to properly replace Cole could create a major hole.

Los Angeles Angels: Too much focus on Gerrit Cole

The Angels are widely regarded as one of the early favorites to sign Cole, and that may very well be where the AL Cy Young runner-up lands this offseason.

However, unless he's suddenly capable of starting 162 games, it's going to take more than just one pitcher to overhaul a starting rotation that finished 29th in the majors with a 5.64 ERA. If it's one or the other, this team would be better suited signing three mid-level starters than one marquee hurler.

Oakland Athletics: Financial limitations

One of just six teams with a payroll under $100 million this past season, the Athletics nevertheless won 97 games and reached the postseason for a second straight year.

The team's big financial splurges last offseason were a pair of two-year deals for reliever Joakim Soria ($15M) and starter Mike Fiers ($14.1M), and that could be the ceiling on any free-agency action this winter as well. That doesn't mean they can't add talent, but working within the confines of a tight budget will again be an unavoidable hurdle.

Seattle Mariners: A diminished market for Mitch Haniger

The Mariners are open to the idea of trading outfielder Mitch Haniger, according to Ken Rosenthal of The Athletic, and there should be plenty of interest despite the fact that he is coming off an injury-shortened season in which he played just 63 games.

The 28-year-old was a 6.1 WAR player in 2018. While he's due for a significant raise in his first year of arbitration, his upside is considerable, and team control through the 2022 season makes him an appealing buy-low target. The question here is how low the M's are willing to sell, and whether they can get a worthwhile return.

Texas Rangers: A relatively thin starting pitching market

According to Jeff Wilson of the Fort Worth Star-Telegram, the Rangers could look to add as many as three starting pitchers this offseason in an effort to solidify the staff behind the veteran duo of Lance Lynn and Mike Minor.

Achieving that could be tricky considering there's a fairly significant drop-off beyond Gerrit Cole, Stephen Strasburg, Zack Wheeler, Madison Bumgarner, Hyun-Jin Ryu, Dallas Keuchel and Michael Pineda. The team is also focusing some attention on the likes of Anthony Rendon and Josh Donaldson as potential upgrades at third base, which could divert some of their funds.

Atlanta Braves: Clinging too tightly to prospects

Led by a homegrown core that includes former top prospects Ronald Acuna Jr., Ozzie Albies and Mike Soroka, the Braves have won back-to-back NL East titles. Now it's time to use some of their prospect capital to improve in the short term with their window of contention wide-open.

If landing an established veteran starter means parting with some of the team's young pitching talent, they can't allow that to become a roadblock as they look to improve for a World Series push in 2020.

Miami Marlins: A lack of assets

The harsh reality for the Marlins is that they're not yet in a position to spend and they don't have much in the way of attractive trade assets.

Breakout starter Caleb Smith faded down the stretch and won't bring the same return he would have over the summer, and Sandy Alcantara and Brian Anderson are the closest thing the franchise has to long-term building blocks. There's not much to be done here, besides waiting on the farm system to develop.

New York Mets: A thinned out farm system

The Mets parted with top prospects Jarred Kelenic and Justin Dunn in the blockbuster deal to acquire Robinson Cano and Edwin Diaz last winter, and then doubled down with another big trade to acquire Marcus Stroman at the deadline, giving up two of their best pitching prospects in the process (Anthony Kay and Simeon Woods-Richardson).

As a result, the farm system has been thinned considerably, and that could make further activity on the trade market tricky. Instead, they may have to focus their improvement efforts solely on the free-agent market.

Philadelphia Phillies: Significant money already on the books

The Phillies already have $121.2 million on the books in 2021 and $110.6 million committed to the 2022 roster. A extension for catcher J.T. Realmuto would add another significant financial commitment in the years to come.

That could limit the club to second-tier free agents and the trade market, and that cuts out some of the more appealing options for upgrading a starting staff in serious need of additional help. Another year of the status quo in the rotation simply will not cut it.

Washington Nationals: Waiting around for Anthony Rendon, Stephen Strasburg

Ideally, the Nationals would find a way to bring back Anthony Rendon and Stephen Strasburg this offseason, but there's no guarantee it's going to happen.

If things aren't progressing toward a reunion, the front office has to pivot to a Plan B before the free-agent market is tapped dry and the Nationals are left with two glaring holes on the roster where those two standout players used to be.

Chicago Cubs: The juggling act of adding while subtracting

If the Cubs are going to make a splashy addition this offseason, it will likely come by way of trading away a key piece of the position-player core. Whether it's Kris Bryant, Willson Contreras or Kyle Schwarber, there's a good chance a key figure in the team's recent history will be on the move.

Trading MLB talent in the midst of contention is always a juggling act, with the obvious risk of plugging one hole and immediately creating another. A blockbuster free-agent signing appears unlikely, and it's clear the roster needs a shake-up, so deciding how to go about doing that will define the offseason.

Cincinnati Reds: A thinned out farm system

With Nick Senzel graduating to the majors and Taylor Trammell traded to the San Diego Padres, the Reds farm system fell to the No. 18 spot in B/R's final 2019 rankings.

This team is committed to contending in 2020, and the front office has not been shy about pulling the trigger on some big trades in recent seasons. Assuming the Reds don't want to sell low on Hunter Greene, is Nick Lodolo or Jonathan India a good enough centerpiece to facilitate a blockbuster trade? It's a fair question, especially if they decide to make a run at someone like Mookie Betts.

Milwaukee Brewers: An aversion to large contracts

The Brewers finished the 2019 season with a roughly league-average payroll of $135.9 million, so lumping them in with teams like the Rays and Athletics would not be accurate. But this team has certain financial hurdles.

Matt Garza (4/$50M) and Lorenzo Cain (5/$80M) represent the largest free-agent contracts in franchise history, and it's almost certainly going to cost more than that to sign the market's top starting pitching options. Another offseason of ignoring the rotation would be a mistake.

Pittsburgh Pirates: Organizational instability

After a tumultuous season both on and off the field, the Pirates gutted the coaching staff and the front office. Former Red Sox general manager Ben Cherington is now guiding the ship, and he's essentially starting from scratch as far as structuring the organization.

The first step will be filling the vacant manger's seat and filling out the coaching staff. The next step will be deciding whether to blow things up entirely or go for a smaller-scale retooling of the roster. Those are huge decisions, and the winter meetings are already fast approaching.

St. Louis Cardinals: A tough decision on Carlos Martinez

According to Ken Rosenthal of The Athletic, the Cardinals were willing to move Carlos Martinez ahead of this summer's trade deadline. The former ace of the staff has spent the majority of the past two seasons pitching out of the bullpen in an effort to stay healthy, nailing down 24 saves in 27 chances with a 3.17 ERA in 2019 after replacing Jordan Hicks in the closer's role.

With two years and $23.4 million left on his contract and two club option years following that, he is an expensive reliever. His track record, however, gives him bounce-back potential as a starter. Moving him could be a great way to create some payroll flexibility, or it could be a huge mistake.

Arizona Diamondbacks: A diminished market for Robbie Ray, David Peralta

If the Diamondbacks had flipped starter Robbie Ray and outfielder David Peralta last offseason, they would have bagged a significantly better haul than what they might receive this winter. Both players are free agents after the 2020 season and therefore profile as rentals.

Ray had another strong season in 2019 and should still have solid value, but not what it might have been if the team had sold high. Meanwhile, Peralta followed up a 127 OPS+ and a career-high 30 home runs in 2018 with a 106 OPS+ and just 12 long balls, and it's hard to see him bringing back much beyond a mid-level prospect.

Colorado Rockies: An obligation to contend

The Rockies signed Charlie Blackmon to a six-year, $108 million extension in April 2018 and Nolan Arenado to an eight-year, $260 million extension in February. To pivot now and blow things up would be a tough pill to swallow for everyone involved.

At the same time, this team was a complete mess last season, due in large part to regression from the pitching staff to a 5.56 ERA. On the heels of a 71-91 season, the front office has a lot of work to do if this team is going to contend in 2020. But what choice do the Rockies have?

Los Angeles Dodgers: An extremely thin relief pitcher market

One major domino already fell on the relief pitcher market when Will Smith signed with the Atlanta Braves. That leaves Will Harris, Drew Pomeranz and health question mark Dellin Betances as the cream of the free-agent crop.

It's no secret the Dodgers need bullpen help, and even closer Kenley Jansen was not his usual dominant self last season. The lack of available options mean they will need to move quickly. Otherwise, they will be forced to turn to the trade market or to rely on unproven and previously underwhelming options.

San Diego Padres: A limited number of frontline pitching options

The Padres need an established ace to front a young rotation on the rise. Top prospect MacKenzie Gore has front-line potential and Chris Paddack impressed as a rookie, but plugging a proven innings-eater into a spot at the top of the staff would go a long way.

The trouble is, only a handful of guys fit the bill, and after a 92-loss season the Padres are still in "prove-it" mode as far as their ability to contend is concerned. Even if they focus their efforts on the trade market, there's no guarantee a top-tier starter even hits the block this offseason.

San Francisco Giants: An unclear direction

All it took was a hot streak in July to convince the Giants they were capable of contending in 2019. They balked at trading Madison Bumgarner and Will Smith and now they will settle for draft-pick compensation rather than a significant prospect haul.

There are still a number of high-priced veterans on the roster, which could be driving the organization's desire to contend in the short term, but it's fairly clear this team should be focused on the future. Any moves that are made this offseason have to be made with one eye on the future.

All stats courtesy of Baseball Reference and FanGraphs, unless otherwise noted.