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- Senior writer ESPN Magazine/ESPN.com
- Analyst/reporter ESPN television
- Author of "The Last Night of the Yankee Dynasty"

The 2025 Toronto Blue Jays serve as a benchmark for several MLB executives weighing their clubs' odds of advancing far into October. The Jays posted middling results through the first half of last season, then rallied in the second half to come within one run and two outs of defeating the dominant Los Angeles Dodgers in the World Series.

National League squads, along with those stuck in the American League morass, can envision extended postseason runs that will shape their decisions ahead of the 6 p.m. ET trade deadline on Monday.

Below are the teams most eager for action, the spots they should target and possible trade fits.

1. Chicago Cubs: Starting pitching

Cade Horton was expected to anchor the staff with swing-and-miss stuff, yet he managed only 7 1/3 innings before an elbow issue ended his season. Justin Steele was counted on after his own injury but suffered an early setback. Edward Cabrera arrived via a costly offseason deal only to suffer a major leg injury in June. Jameson Taillon, the highest-paid pitcher on the roster, was recently designated for assignment.

The Cubs therefore require pitching depth of any kind. Options appear plentiful, ranging from Freddy Peralta and Clay Holmes to Robbie Ray, Kevin Gausman, Reid Detmers and possibly Tarik Skubal or Casey Mize.

The position-player core remains strong and the Cubs may enjoy the best home-field edge in baseball, yet deeper October progress will likely require more arms.

2. Chicago White Sox: Catcher, starting pitcher

A leap from 121 losses two years ago to a World Series appearance is conceivable given the White Sox's rising talent and the AL's overall softness. The loss of catcher Kyle Teel to a serious ankle injury hurts, however, and another backstop would help. Kyle Stephenson and Jose Trevino from the Reds form one intriguing duo, while the Mets may entertain offers for Francisco Alvarez and Luis Torrens.

Noah Schultz owns an ERA above 6.00 in the fifth-starter role, so an upgrade there would also be welcome.

3. New York Yankees: Bullpen arm, right-handed hitter

Injuries to Aaron Judge, Giancarlo Stanton and Cody Bellinger have thinned the lineup, yet the Yankees' clearest deadline priority appears to be a power reliever capable of matching elite October lineups. Mason Miller would be ideal and Adrian Morejon would also help, though San Diego's willingness to move either remains uncertain.

A right-handed bat is another target. Ryan Jeffers has been linked since May and would fit well if Minnesota shows interest in moving the pending free agent. Homegrown options could surface as well, and Tyrone Taylor of the Mets represents one possible addition.

Bullpen reinforcement remains the top need; acquiring a Miller or Morejon could supply the late-inning strength required for October success.

4. Atlanta Braves: Starting pitcher

Atlanta will monitor whether Detroit moves Skubal or Mize. The Braves' farm system is well positioned to pursue Skubal, with JR Ritchie potentially headlining a package. Should the Tigers retain Skubal or send him elsewhere, other rotation options will be explored.

5. Tampa Bay Rays: Starting pitcher

The Rays lead the AL, yet their rotation carries injury history. Shane McClanahan has reached 96 innings after missing the prior two seasons, and Drew Rasmussen has thrived despite past ailments. Additional depth would help the club reach the World Series for the first time in 18 years.

That backdrop explains why Tampa is viewed as a quiet contender should bidding for Skubal intensify.

6. Seattle Mariners: Right-handed hitter

Seattle remains enigmatic after last October's playoff run. A club featuring Julio Rodriguez, Cal Raleigh and Josh Naylor has underperformed and now risks missing the postseason. After dropping three of four to Texas, the front office must decide whether any addition can salvage the year. A right-handed bat to revive the offense is the clearest need, as the club ranks 28th in OPS versus left-handed pitching.

7. Philadelphia Phillies: Starting pitcher, reliever

The Phillies are 43-16 when Cristopher Sanchez, Zack Wheeler and Jesus Luzardo start but just 14-34 otherwise. Aaron Nola has struggled and the fifth spot has been unreliable, so a veteran starter is expected. Brad Keller's injury has also thinned the bullpen, and rival executives anticipate a reliever addition as well.

8. Milwaukee Brewers: Starting pitcher

Milwaukee posted baseball's best record last season yet ran low on pitching by the division series. Jacob Misiorowski has emerged as an ace, but Kyle Harrison's injury creates a need for another starter both now and in October. A reunion with Freddy Peralta or a pursuit of Skubal or Robbie Ray are among the possibilities.

9. Pittsburgh Pirates: Bullpen help

After speculation about general manager Ben Cherington's future a year ago, Pittsburgh has improved and become dangerous. Rival evaluators praise the rotation and offense, yet the bullpen ranks 24th in ERA. High-leverage relief help is a priority, and the Pirates are expected to be aggressive before the deadline.

10. Texas Rangers: Bullpen arm

Texas is not positioned to absorb salary but requires relief depth while defending the AL West lead. Creative trade structures will be explored.

11. Cleveland Guardians: Any kind of offense

Early focus centered on a right-handed hitter, but with the offense struggling the Guardians will consider broader upgrades. Lane Thomas of the Royals could be one fit.

12. Boston Red Sox: Shortstop

Boston acquired Curtis Mead to address the need for a right-handed infielder, yet rival executives say the club continues to seek a shortstop. Interest in Zach Neto and C.J. Abrams has surfaced, and the Red Sox have also checked on Miami's Otto Lopez, who leads the majors with a .328 average.