With that in mind, let’s take a look at three teams in particular that are probably feeling an increasing sense of urgency to improve their rosters before all the best solutions are spoken for. Onward. 
Stupidly, Cubs ownership appears to be forcing the team to freeze or cut payroll despite designs on the World Series and a third-place finish in 2019. That’s why the Cubs by all accounts are considering trading a core contributor like third baseman Kris Bryant or catcher Willson Contreras in order to address roster needs elsewhere. 

Los Angeles Dodgers

MLB’s Winter Meetings are freshly behind us. While more than billion changed hands in the form of guaranteed free-agent contracts — most notably to Stephen Strasburg, Gerrit Cole, and Anthony Rendon — some contenders and aspiring contenders have been curiously quiet thus far in the 2019-20 offseason. Now that so many big names are off the board and so many competitors have made big additions, the pressure is mounting upon these relatively inactive clubs. 
Speaking of the Cubs’ roster, one can argue it’s the strongest in the NL Central, but — to repeat — they finished behind the Cardinals and Brewers last season. As well, the Reds figure to be improved. What the Cubs should be doing as they attempt add a second title to their current run is adding pieces via free agency. That, however, requires payroll investments, and the Ricketts family isn’t willing to do that. The Cubs need another known quantity in the rotation, and they also need some bullpen help. One could also argue that the outfield isn’t what it needs to be for a team with World Series aspirations. Again, though, because the Cubs don’t want to get deeper into CBT territory, trades that likely involve some level of salary offset are the only real paths toward change. Such approaches always carry with them a “robbing Peter to pay Paul” risk. 
The Rangers, coming off three straight losing seasons, are looking to build momentum and enthusiasm as they move into brand new Globe Life Field. Hey, they’ve got new uniforms and everything. And, on Sunday, they acquired two-time Cy Young winner Corey Kluber from the Indians. It was a significant move that gives Texas its new ace. But they could still use move to get a headline-grabbing bat on the roster.  Yes, the Dodgers have claimed seven straight NL West titles, and they’ll be prohibitive favorites to make it eight in a row in 2020. They’ve also won pennants in two of the last three seasons, so these are hardly desperate times in Chavez Ravine. That said, the prevailing reality is that the Dodgers haven’t won the World Series since 1988, which makes for the 10th-longest current title drought in MLB

Texas Rangers

Elsewhere, the Dodgers have been linked to Josh Donaldson and incumbent lefty Hyun-Jin Ryu. Neither of those moves the needle or invigorates the customer base like Lindor. Right now, the club’s marquee offseason addition is a reliever who last season posted an ERA of almost 5.00. That can’t continue to be the case.
Compounding such miseries for Dodger fans is that the club — one of the richest in all of sports — has emphasized payroll efficiency in their half-decade plus under president of baseball operations Andrew Friedman. That hasn’t prevented them from continuing to lord over their division — and as noted they’ve played in two of the last three World Series — but it has prevented them from spending in keeping with their vast revenues. For instance, under Friedman the Dodgers have yet to agree to a nine-figure contract and have plainly operated with one eye on the Competitive Balance Tax threshold (right now, L.A. has more than million of room under the CBT line and is barely running a top-10 payroll). 

Chicago Cubs

The expectation of an active winter has led to the Rangers being linked to notables like Rendon, Cole, and Donaldson. The first two obviously won’t happen, and it was recently reported that Texas is out on Donaldson. They’ve been linked to Lindor, but it seems unlikely that the Rangers have the quality and quantity of prospects to get such a deal, especially given the likely demand for Lindor’s services. Recently, free agent and trade target names like Nick Castellanos, Ryu, Maikel Franco, and Robinson Chirinos have come up. However, when you share a division with the Astros, Athletics, and improved Angels and are coming off an 87-loss season, those are half-measures at best. The Rangers raised expectations coming into the offseason, but they’re yet to make good on them. Our own R.J. Anderson took a look at the four positions where the Rangers need to add before spring training. Thus far, it’s been a particularly frustrating winter for Dodger rooters. Early offseason rumors credibly tied the Dodgers to the big three free agents Gerrit Cole, Anthony Rendon, and Stephen Strasburg. They missed on all three, and they reportedly didn’t even make an offer to Rendon. Yes, the Dodgers won 106 games last season, but a team with such riches that’s still spoiling for a title should be seeking out every conceivable roster improvement. Post-Strasburg/Cole/Rendon, the Dodgers have been linked most notably to Indians star shortstop Francisco Lindor. Such an add would relieve much of the vexation presently running through the fan base, but that will also require Friedman to take on salary and give up years of control. He seems to be fond of neither of those things.