If Championships are the goal, which team would you choose: Blue Jays or Dodgers?

Put yourselves in the shoes of “he who shall not be named”, and imagine you were testing free agency for the first time after six years in the majors, with the Rookie of the Year, two MVP and Silver Slugger Awards, and three All-Star selections on your resume. Add in the fact that, at age 29, you hadn’t played on a team with a winning record or any playoff appearances since arriving in 2018.

In fact, your team finished in 4th place in the AL West five of those six seasons, with a lone 3rd place finish in 2022, 33 games back of the Houston Astros. But you are an extreme competitor, with a strong desire to win; and, despite playing alongside an 11-time All-Star and three-time MVP, the closest you got to postseason glory was striking that dude out to win the World Baseball Classic in March.

A whole country watches your games live, and more than anything, they want to see you play meaningful baseball in October. As your countryman and former Blue Jay Munenori Kawasaki said, “I want to see [he who shall not be named] in action in the playoffs.”

Fast forward to the end of 2023, after your team struggled to a 73-89, 4th place finish. After losing the home finale 5-1 to the Mariners, your frustration with all of that losing was obvious: “I really like the team. I love the fans. I love the atmosphere of the team. But, more than that, I want to win. That’s the biggest thing for me. I’ll leave it at that.”

I want to win.

So if the desire to win was paramount after zero playoff games in six seasons, and it came down to two finalists, how would go about deciding where to spend the next ten years of your life through your age 38 season? Let’s assume the money on the table and the terms were likely similar, and that both teams were in big markets with plenty of marketing and endorsement opportunities.

With an MLB franchise willing to commit more than a half a billion dollars for your talents, likely the commitment of ownership and the front office to winning would be top of mind. Perhaps the recent track record of the team and front office would be important; and, their commitment to the core of the team and the availability of MLB-ready talent in the farm system would both factor in as well given the ten year term.

Ownership and front office

According to former infielder and current SportsNet LA broadcast analyst Jerry Hairston Jr., who was just finishing his career when the Guggenheim Baseball Management group bought the Dodgers in April 2012, “We could feel the energy through them. From Day 1, they did everything. They did even more than they had promised.”

The Dodgers have been to the playoffs for eleven straight seasons - every year since 2013, including six NLCS appearances and three World Series appearances, plus the 2020 World Series Championship. Longtime ace Clayton Kershaw, the lone player remaining from the 2012 season, is thankful for the success, and for the ownership support that has made it possible.

“If you talk to.. all these guys [in the ownership group], they’re invested… when they are around, they know what is going on, and I know they keep tabs and they send text messages and tell you ‘good job.’ That’s just cool, to have an ownership group like that,” said Kershaw on the 10th anniversary of them purchasing the club.

Dodgers’ President of Baseball Operations, Andrew Friedman, has led the front office since the 2015 season, with eight NL West titles, three National League pennants and the 2020 World Championship since he was hired. The team has an 845-512 record since then for a .623 winning percentage, including a franchise record 111 wins in 2022. Dave Roberts has been his manager since 2016, with a .630 winning percentage in eight seasons.

The Blue Jays have only won one AL East title (2015) since Rogers Communications bought the team in 2000. They’ve been to two ALCS series since then, but haven’t been to a World Series since winning in 1993.

Owner and team Chairman Edward Rogers does not give out the vibe that he’s texting his ace Kevin Gausman after a win and telling him ‘good job.’ In fact, you don’t ever see the broadcast cutting to a shot of Rogers in his executive box at any games, including during the playoffs.

One wonders if he was in Dunedin last week to welcome and pitch a deal to a certain Japanese free agent who was reported to have met with Toronto execs? We can be sure that the Dodgers ownership was actively involved in their sales pitch.

No one really seems to know what he or the other Rogers executives think about the team. Toronto Sun sports columnist Steve Simmons reached out to Rogers after the wild card series loss this year to gauge what he was thinking about the state of his team. He received no response, so was left asking, “Which side is Edward Rogers on? What does he believe? And when, if at all, will we hear from him?”

It’s fair to say that Ed Rogers is an aloof owner. Simmons tells a story of how on the day that former GM Alex Anthopoulos decided to walk away from six seasons in the dream job he loved with the Jays, “Rogers surprised him almost out of nowhere with a lucrative offer… Before the offer, the two had never met. The de facto owner had never met the general manager.”

Since Mark Shapiro and Ross Atkins were hired after the 2015 season, the Blue Jays have a 609-585 record for a .510 winning percentage. They’ve been through three different managers, with John Schneider currently signed through the 2025 season, with a club option for 2026.

Payroll

The Dodgers have had a top five MLB payroll every season since 2013, the first full-season after the Mark Walter-led group bought the team. Since Rogers Communications bought the Blue Jays in 2000, they have never had a top five MLB payroll. According to Cot’s Baseball Contracts, the Blue Jays 2023 competitive balance tax payroll of $258M ranked 6th in MLB, while the Dodgers were 4th at $267M.

Of LA’s core, Freddie Freeman is signed through 2027, Mookie Betts through 2032 and Shohei Ohtani through 2033. The Blue Jays currently only have José Berríos signed through 2027-28, but he can opt out of his contract after 2026 in his age-32 season. The current front office hasn’t extended any of their young, homegrown core beyond their arbitration eligible years.

Farm System

What about waves of MLB-ready talent coming from the farm system and player development? Let’s compare the Dodgers' 26-man 2023 NLDS roster to the Blue Jays' 2023 ALWC roster. The Dodgers playoff roster included five rookies they’d drafted and developed in Bobby Miller, James Outman, Ryan Pepiot, Emmet Sheehan and Michael Grove.

All of them except Pepiot appeared in the series. The Dodgers' farm system ranked 6th in MLB Pipeline’s midseason re-ranking even after all of those graduations, with five more prospects in the top 100. Using FanGraph’s future value based ranking, the Dodgers rank 6th as well, with an expected future value of their prospects of $220M.

The Blue Jays' 2023 ALWC roster featured two rookies, Davis Schneider and Cam Eden, neither of whom played. Using the same MLB farm rankings, Toronto’s system ranked 25th, with two top-100 prospects in Ricky Tiedemann and Orelvis Martinez. Using FanGraph’s ranking, they are the only two players with a future value (FV) of 50 or higher in the Blue Jays system, which they only project having an FV of $123M.

So if winning was your goal, which organization would you choose?

Back to you. Removing emotion and confirmation bias as a Blue Jays fans from your decision, and trying your best to be reasonable based on what you know from the above analysis, if you wanted multiple World Series rings over the next 10 years - knowing that your post-career earnings power and Hall of Fame credentials would be enhanced by lots of postseason success, which team would you choose: the Toronto Blue Jays? Or the Los Angeles Dodgers?

Would you prefer the ownership style of Ed Rogers or the group led by Mark Walter, that includes Magic “Showtime” Johnson? Which farm system is likely to produce more complementary MLB-ready talent over your 10-year term? And why would you defer $680M, knowing that ownership was committed to more additions?