The Toronto Blue Jays’ decision to part ways with closer Jordan Romano marks the end of an era. With Romano gone, the franchise’s only remaining link to Alex Anthopoulos’ tenure is the powerhouse first baseman, Vladimir Guerrero Jr.

Romano’s departure came as no surprise, given his $7.75 million projected arbitration salary and the lingering concerns over his elbow surgery recovery. Nevertheless, it’s a move that underscores the Blue Jays’ willingness to take calculated risks, evidenced by previous signings such as those of Kirby Yates and Chad Green, both of whom came with their own sets of injury uncertainties.

As Toronto navigates the offseason, Guerrero stands as a pivotal figure in their plans. The slugger, a four-time All-Star and 2021 AL MVP finalist, is projected to command $29.6 million in his final year of arbitration in 2025 before entering free agency.

At only 25 years old, his potential free agency, absent a long-term contract extension, has Blue Jays fans on edge. Guerrero was signed as a promising 16-year-old in 2015 during Anthopoulos’ final year in Toronto, with then-scouting director Ismael Cruz noting Guerrero’s natural prowess, even as a preteen.

A look back at the legacy of Anthopoulos’ era reveals the shifts in Toronto’s roster landscape. Players from his tenure have accumulated a combined 60.5 bWAR (Baseball Reference’s wins above replacement) after leaving via trades, free agency, or release.

These exits have been partially mitigated by acquisitions under team president Mark Shapiro and general manager Ross Atkins, whose replacements have collectively added 43.5 bWAR. Yet, the situation remains fluid, with long trade trees, such as those involving Erik Swanson and José Berríos, still developing.

To highlight, players like Edwin Encarnación left big shoes to fill, managing a 7.2 bWAR post-Blue Jays. However, his replacements, Kendrys Morales and Steve Pearce, could muster only a combined 1.4 bWAR, illustrating the talent gap Toronto’s management has been aiming to close.

Other trade dynamics, such as the complex networks stemming from Anthopoulos-era players, continue to shape the team’s composition and competitiveness. The impact of trades involving Drew Hutchison and Marcus Stroman exemplifies the shifting value calculation, with multiple players contributing varied bWAR outcomes over years.

For Shapiro and Atkins, the challenge of filling roster gaps with limited prospect depth has led to robust free-agent pursuits in recent years. The signings of players like George Springer, Kevin Gausman, and Hyun Jin Ryu have bolstered the team’s war chest, adding a substantial 39.3 bWAR from 2020 onwards. This strength has contributed towards a solid performance record for the team, enhancing their resilience against the backdrop of a fluctuating talent pool.

However, the financial implications of these signings cannot be overlooked. As the Blue Jays navigate payroll constraints, the Romano decision appears to be a strategic funding move in their pursuit of a competitive edge come 2025. The effort to maintain a winning team adds urgency to securing player-specific investments, such as the potential signing of Juan Soto.

In terms of player retention, Toronto’s front office has struggled to lock in homegrown stars for the long haul. Only Randal Grichuk and José Berríos have been signed to extensions exceeding five years, leaving prized talents like Guerrero and Bo Bichette without long-term deals.

This season could very well determine whether Guerrero decides to explore free agency or solidify his future with the Blue Jays. If he chooses to leave, it would mark the end of a significant chapter, with no Anthopoulos-era players remaining to carry forward that legacy.