Throughout the Rockies’ franchise history, the team hasn’t been shy about extending key members of the roster. Colorado’s biggest extension yet could be in the offing, as the Rockies continue to talk with All-Star third baseman Nolan Arenado about a long-term deal that would keep Arenado away from free agency next winter.

If such a contract is worked out, it would easily be the most expensive deal in Rockies’ history, not to mention one of the pricier deals in Major League history. It would also be the second major extension completed by Jeff Bridich in his time as Colorado’s general manager, coming on the heels of the club’s five-year extension with Charlie Blackmon last spring. That deal is worth revisiting now, given what we’ve seen about the free agent outfield market (or, really, just the free agent market in general) after a second consecutive slow offseason of signing activity.

Blackmon was 31 at the time of the extension (he turned 32 last July 1), and, like Arenado is now, also a year away from reaching free agency. Blackmon had posted solid numbers as a part-time player and then as a regular with Colorado in 2013-15, though he stood a big step forward to hit .327/.390/.578 with 66 homers over 1366 plate appearances in 2016-17. That performance saw Blackmon earn a Silver Slugger Award in both seasons, as well as a fifth-place finish in NL MVP voting in 2017.

With the Rockies coming off a postseason appearance in 2017, the team moved to lock up a top performer, agreeing to an extension that guarantees Blackmon at least $94MM from 2019-23. Blackmon earns $21MM in each of the next three seasons, and then has a player option for another $21MM season in 2022. He then has another player option year for 2023 worth $10MM in guaranteed money, though another $8MM is available via escalators based plate-appearance thresholds that seem rather readily achievable, or on MVP finishes. (The deal also technically adjusted Blackmon’s previously agreed-upon $14MM arbitration salary for 2018, turning $2MM of that figure into a signing bonus.) All told, the extension could max out at $102MM in new money for Blackmon once all is said and done.

Even sticking to the guaranteed $94MM figure, however, Blackmon’s contract already looks like an outlier in the wake of how baseball’s free agent marketplace has evolved over the last two winters. Manny Machado and Patrick Corbin are the only 2018-19 free agents who earned more than $94MM in guaranteed money this winter. Bryce Harper will be the third name on this list once he eventually signs, and it’s doubtful that Dallas Keuchel will meet even MLBTR’s four-year/$82MM projected contract, let alone a $94MM deal.

Blackmon’s production also took a bit of a step back in 2018, as he hit .291/.358/.502 with 29 homers over 696 plate appearances. Still strong numbers, to be sure, though more in the vein of a solidly above-average hitter (116 wRC+, 115 OPS+) than his more elite production (137 wRC+, 136 OPS+) in 2016-17. On the defensive side, Blackmon had been a below-average but playable center fielder throughout his career, though his glovework fell off (-28 Defensive Runs Saved, -12.6 UZR.150) to such an extent in 2018 that the Rockies will now deploy him as a right fielder this season.

Had Blackmon been a free agent this winter, his most natural comp was another center fielder, A.J. Pollock. The newly-signed member of the Dodgers outfield lacks Blackmon’s durability and longer track record of production, but Pollock is also 17 months younger, a more stable defender, and more of a sure thing to produce in a new ballpark (Blackmon has a career .970 OPS at Coors Field, and only a .745 OPS on the road). Pollock landed a five-year deal from the Dodgers worth $60MM in guaranteed money, so even if some teams felt that Blackmon was the better free agent bet, the gap between the two players surely wouldn’t have been $34MM.

With all this in mind, it’s fair to say that Blackmon and his representatives at ACES did a good job in landing that extension last spring. As a soon-to-be 33-year-old headed for corner outfield duty, as hard to imagine Blackmon would’ve found five years and $94MM in free agency if he had tested the market this winter.

A win for Blackmon, however, doesn’t at all mean that the deal was a “loss” for the Rockies. As noted, Blackmon was still a very productive hitter in 2019 — drastic home/road splits aren’t as big an issue when you’re the team that plays at Coors Field, naturally. Blackmon also wouldn’t be the first player to improve at the plate after shifting to a less-demanding defensive position, so getting out of center field could help Blackmon’s bat as well as simply drastically elevating his defensive value.

Could Colorado have re-signed Blackmon to a lesser deal as a free agent had they not extended him a year early? Potentially, though such a “what-if” scenario is easy to create with 20/20 hindsight (plus, you never know if another team might’ve been particularly keen on signing Blackmon). As it worked out, the Rockies were able to retain a player they liked both on the field and in the clubhouse, even if it may have been a bit of an overpay.

Let’s also not overlook the big-picture ripple effect of the Blackmon extension as it relates to Arenado. The third baseman now has solid proof that a Bridich-led front office is willing to pay to keep a homegrown star in the fold, and retain members of what has been a winning core group that has reached consecutive postseasons. Money-wise, Blackmon’s long-term contract presents no real obstacle to the Rockies being able to afford Arenado, given that negotiations are already taking place and the organization is cognizant of the $200MM+ it will surely take to keep Arenado in the fold. From a return-on-investment standpoint, Blackmon’s contract also looks like much less of a problem for the Rockies’ payroll than the lack of production they’ve received from recent free agent signings like Ian Desmond, Jake McGee, or Bryan Shaw.

It will also be interesting to see how Blackmon’s extension stands in the wider scope of future extensions for star players a season away from free agency. We’ve already seen some notable extensions this spring, though those deals went to players (Aaron Nola, Luis Severino, Jorge Polanco, etc.) who were still arbitration-controlled for several seasons, rather than pending members of the 2019-20 free agent class. For some of those scheduled free agents who are already in their 30’s, the thought of an extended stint in free agency and/or a lesser contract than expected have surely crossed these players’ minds in the wake of the last two offseasons.

Blackmon’s contract may represent a best-case scenario for such players if they do pursue extensions, as Blackmon and his camp were able to score at what may be the peak of the outfielder’s value and earning potential. Of course, it takes two to tango, and it remains to be seen if teams besides the Rockies are willing to pay a premium in an extension for a player who isn’t either a true elite veteran (like a Nolan Arenado) or a younger, arbitration-controlled star who could prove to be a bargain if locked up early. As a team wanting to both win now and to send an early signal to Arenado that they wanted to win the future, however, the Rockies felt Blackmon’s extension was clearly worth the plunge.