Timing is everything for a Trout contract extension

Over the last two years, the baseball world's favorite distraction during slow news cycles has been to pontificate on what Mike Trout's potential contract extension with the Angels could look like. That little game might soon become invalid though as reports from the Angels camp are that Trout and the team are going to sit down and see if they can't work something out.

As fun as it is to guess at the potentially massive sum of dollars Arte Moreno will give Trout, what we really need to focus on is the timing of everything involved. Those predictions of Trout setting a new record for his contract are entirely dependent upon the various timings of his deal.

The biggest timing element, of course, will be the length of time the eventual deal covers. For all of those predicting that Trout is going to somehow land a $400 million contract, they need to take into account the contract duration that would require. For anything outlandish like that, we would be talking about a ten, eleven or even twelve year contract. Those kind of deals are fun to imagine, but they aren't really practical. Of all the high profile players that have signed extensions over the last few years, the longest that has been signed is Buster Posey at nine years with a handful of other players signing for eight years. If anyone is worth going 10 or more years for, it is Trout, especially given his youth, but that's still a massive commitment on the part of the team.

Of course, we've seen the Angels give out one of those 10-year deals already to Albert Pujols. Robinson Cano received an identical deal this winter, so that kind of contract certainly isn't unprecedented, but again, timing is critical. For Cano and Pujols, those contracts have come at a time in their career where they are essentially signing their very last big contract and doing so as they exit their prime years. They were also on the open market, not negotiating with one and only one suitor. Trout, at the tender age of 22, is signing his first big contract and doing so as he heads into his prime years. That is a huge differentiator.

Where age most comes into play is that Trout and his agent will want to think long and hard about Trout getting his second big contract. Cano and Pujols got their blockbuster deals going into their age 31 and 32 seasons, respectively. Trout, however, could sign an eight-year deal, which would put him on the open market headed into his age 30 season. That's a difference that could mean an extra few dozen million dollars for him on that second contract. Whether that is a big motivator for Trout remains to be seen, but his agent wouldn't be doing his job if he didn't give strong consideration to how he sets his client up for his next contract.

His agent might even have Trout think long and hard about exactly when he does agree to an extension. Trout is coming off of two incredible seasons, but how much more could he earn if (ok, when) he has a third incredible season? Not only does that give him a stronger track record to negotiate with, but if he waited until after this season, he'd be headed into arbitration, which would put additional pressure on the Angels to get a deal done lest they want to take their chances in an arbitration setting where Trout would almost certainly set a new record.

That potentiality should be all the motivation the Angels need to get a deal done now, but there is actually plenty more reasons to act quickly. One of the most pressing is that other young players are starting to sign big extensions and those extensions are not the team-friendly deals that had been the norm just a few years ago. We already saw Clayton Kershaw get his seven-year, $215 million megadeal with a sweetheart out-clause after five years. A year ago, Elvis Andrus signed for a stunning eight years and $120 million while Buster Posey inked a nine-year, $167 million pact.

On a more comparable level, Freddie Freeman signed an eight-year, $135 million extension just last week. This should be the focal point for Jerry Dipoto as he preps for negotiations because of just how much money Freeman got. Though he is two years older and a year ahead on service time (but his deal covers the same career span the Angels are targeting with Trout), Freeman signed a deal that really was not discounted much at all. This is for a player that has just one All-Star caliber year as opposed to two MVP-caliber years. His new deal bought out five years of free agency at values ranging from $20.5 million to $22 million. That seems pretty spot on with what he would've gotten in free agency if he had been able to keep playing at a 5-win level. That combined with Clayton Kershaw getting paid $30+ million for his free agent seasons does not bode well for the Angels getting even a modest discount in exchange for locking up Trout so early.

As such, they best move now before the value trend shifts even further in the favor of the player. The last thing they want to happen is for Trout's closest comparable, Bryce Harper, to beat them to the punch, setting the floor for Trout's potential extension even higher.

There is also the small matter of exactly when Trout's potential extension would kick in. Rumors persist that the Halos want the deal to start with his 2015 season, but that has long seemed wrong-minded to me. Let's say, based off my best guess, the sides agree to an eight-year, $240 million extension that kicks in in 2015. That would give Trout a $30 million luxury tax number going forward. That's a pretty big number for a team that is already right up against the tax threshold. However, if they were to include 2014 in that deal, say for $3 million, that would bring his number down to $27 million. That's $3 million shaved off his tax number. It would put the Halos over the tax line in 2014, but as a first time offender, it would be a pretty minimal hit. What it would do though is make it easier for the Angels to stay under the tax line in 2015 and beyond. That could make a big difference for the Angels' plans in 2015, 2016 and 2017 as they work their way out from under the big deals of Hamilton, Weaver and Wilson.

That additional flexibility might even play big into Trout's way of thinking as might the team's performance this season. Trout has already burned two 10+ WAR seasons in Anaheim without sniffing the playoffs. What would happen if the Angels wait until next winter to lock up Trout, but suffer another disastrous season this year?

Without trying to get deep inside Trout's head, one would think that certain players would be dissuaded from signing away the best years of their career to a franchise that might struggle to reach the post-season for years to come. Not everyone is as blindly loyal as Felix Hernandez or as slavishly devoted to their bank account as Zack Greinke. If Trout is the type of player who truly just wants to win, another losing season could compel him to forego contract talks altogether or at least look to sign a much shorter agreement (or a deal with an early opt-out) so that he can choose to jump ship to a true contender when he hits his prime.

There are obviously a lot of considerations here for both involved parties. How heavily each side weighs the various factors will determine when Trout signs and for how much. And, like so much of life, timing will be everything.

Garrett Wilson

About Garrett Wilson

Garrett Wilson is the founder and Supreme Overlord of Monkeywithahalo.com and editor at The Outside Corner. He's an Ivy League graduate, but not from one of the impressive ones. You shouldn't make him angry. You wouldn't like him when he is angry.