5.) New York Yankees
The Yankees' front office led by Brian Cashman comes in last place here and frankly, you love to see it. The fact that no one, including the Yankees, understood what New York did at the trade deadline is a microcosm of how the Yankees have been run in recent years. They have found some success in recent years to be sure, but it feels like that has happened despite Cashman's moves instead of being a result of them.
The Yankees have a lot of money tied up in past their prime players like Giancarlo Stanton, Anthony Rizzo, and DJ LeMahieu and that has been indicative of the Yankees' method of "throw money at guys with name recognition" when it comes to roster construction. They do have some young promising players finally getting a chance now, but this is a team that still looks like it is going to continue to get old and require a full reset at some point.
4.) Boston Red Sox
The Chaim Bloom fans out there are going to be upset at this ranking, but again...this is just where things stand right now. Boston has culled popular (and good) players Mookie Betts and Xander Bogaerts with the return for Betts being particularly rough. The Red Sox haven't been as aggressive as fans would have liked and frankly, the results on the field have left a lot to be desired as Boston has finished at or near the bottom of the AL East in three of the past four seasons including this one.
There is some hope with this impending wave of youth for the Red Sox, but Bloom and co. are betting heavily on these young guys being impact players. One thing to keep an eye on this offseason is whether or not Boston throws their weight around in free agency or the trade market. Theoretically, Boston will have room to add some significant payroll and if they add some impact players this offseason, the narrative around the front office could change significantly.
3.) Toronto Blue Jays
The middle of the pack belongs to the Toronto Blue Jays. A lot of what goes right or wrong depends on how well their young duo of Vladimir Guerrero Jr. and Bo Bichette are playing. However, Toronto deserves a lot of credit for their willingness to add impact players from outside the organization to supplement their player development successes.
In recent years, the Blue Jays have traded for Matt Chapman and Robbie Ray and signed free agents Kevin Gausman, George Springer, and Chris Bassitt among others. Toronto could have easily tried to just make their talent pipeline work and hope to hit the lottery. Instead, they have remained aggressive in trying to compete in the division. It hasn't worked out the way they hoped just yet, but they remain a dangerous team and should be commended for swinging big and trying to improve each season.