There’s nothing that excites a journalist quite like a deal coming together past its initial deadline. Vladimir Guerrero Jr.’s 14-year, $500 million contract extension with the Blue Jays came nearly two months after Guerrero’s deadline to end talks at the start of spring training.

It capped off another week of significant extensions across the sport, with Ketel Marte, Jackson Merrill and Kristian Campbell also signing long-term pacts. Let’s break it down.

Vladimir Guerrero, Jr. reaches his mark

Extensions work for younger players because a player forgoes the potential for larger earnings to mitigate the risk of failure before free agency, be it through injury, underperformance, or whatever else. If you’re, say, Kristian Campbell, you take $60 million guaranteed now when you might have been able to make more because there’s also the chance you would have made a lot less. The team takes on that risk in exchange for a discount on the player if the better-case scenarios play out.

But as the player gets closer to free agency, the dynamic inverts. The player’s potential earnings are more secure, and it’s the team that risks losing by waiting. Put the team in a desperate enough situation, and the player can make even more than he might have on the open market.

Guerrero just wielded that exact leverage to hit his desired $500 million mark.

His final push from around $450 million to $500 million is reminiscent of Francisco Lindor’s 2021 extension with the Mets. At that point, the Mets were like these Blue Jays, seeking to reestablish credibility with their fan base by making a big financial commitment. Lindor was able to push the Mets beyond their “best and final offer” to set a new record for a shortstop.

Guerrero’s deal values 13 free-agent years at more than $36 million per season; the full 14-year agreement carries an average annual value of $35.7 million.

Even when adjusting for inflation, that’s the second-largest AAV for a first baseman. Back in February, I broke the contracts for first basemen into three tiers (adjusting for inflation):

• ~$40 million per season (Miguel Cabrera)
• $30 to $32 million per season (Albert Pujols, Prince Fielder, Mark Teixeira, Joey Votto, Freddie Freeman, Chris Davis and Paul Goldschmidt)
• ~$25 million per season (Matt Olson, Eric Hosmer)

Guerrero settles behind Cabrera but ahead of everyone else — a real win for him considering how his track record fits in that cohort. Add in that he also received the longest contract in that group by four years, and this is an outstanding deal for Guerrero that will be viewed as a benchmark for other soon-to-be free agents.

Ketel Marte locks in his future

In general, agreeing to an extension with a veteran well before he’s set to hit free agency is not advisable. You don’t know how even established players will age into their 30s, which is how the Tigers and Phillies ended up with bad deals for Miguel Cabrera and Ryan Howard, respectively.

Those deals were two years early; this one with Marte is essentially four years early, adding his age-35 through age-37 seasons to the extension he’d initially signed with Arizona in 2022. That’s a dynamic we haven’t seen for a veteran since Evan Longoria’s second extension with the Rays (signed in 2013, starting in 2017). Longoria played just one of the six seasons of that extension with Tampa Bay.

This one feels pretty safe, though, when compared to some of the others. Whereas the extensions for Cabrera and Howard didn’t come at legitimate discounts from the open market, this one for Marte does. The Diamondbacks are guaranteeing Marte an additional four years and $67.5 million. (In reality, Arizona was very likely to exercise its 2028 club option on Marte, and so the new deal adds $57.5 million over the subsequent three seasons.)

So the Diamondbacks are valuing those age-35 through age-37 seasons at just over $19 million per year. That’s $5 million less than José Altuve is getting per season in a five-year deal that just started at age-35. (While signed last spring, Altuve’s extension kicked in at the start of this season, right as he moved off second base). Marte’s deal is just slightly above how Ben Zobrist was valued as a free agent entering his age-35 season back in 2016, when he signed for four years and about $18 million in today’s money.

Furthermore, the Diamondbacks’ faith in Marte has paid serious dividends already. This is the third extension between the two sides. Arizona extended Marte in 2018 when he was five years away from free agency and again in 2022 when he was three years away. He’s rewarded that belief handsomely each time.

Jackson Merrill gives the Padres a hand

Of all the extensions signed in the past couple weeks, the Merrill one has confused me the most. That’s probably not a surprise: Last month I suggested he could earn $375 million over 15 years, which is a lot more than $135 million over nine years.

It looks as if a model for Merrill’s deal, which starts in 2026, was Ronald Acuña Jr.’s 2019 extension with Atlanta. That deal bought out Acuña’s arbitration years and four free-agent years (if its club options are picked up) for $134 million. This deal buys out Merrill’s arbitration years and four free-agent years for $135 million. To be fair, there are fairly straightforward escalators here that could land Merrill an additional $30 million. There’s also a club option at $21 million, which could become a player option with a top-five MVP finish.

In the time since Acuña’s deal, the extension market has become much more lucrative, with the deals signed by Spencer Strider, Julio Rodríguez and Bobby Witt Jr. pushing the market forward for pre-arbitration players. Merrill and Rodríguez each compiled 5.3 wins above replacement (according to FanGraphs) in their rookie seasons. Rodríguez’s contract guarantees him $209.3 million; Merrill’s tops out at $204 million.

Of course, signing a nine-figure deal after one major-league season is nothing to sneeze at, and Merrill talked about his connection with the city and the organization as a big reason he wanted to stay long-term.

(Top photo of Vladimir Guerrero Jr. who sits next to shortstop Bo Bichette: Cary Edmondson / USA Today Sports)