Photo courtesy of MLBTradeRumors.com.

On March 28, 2014, Mike Trout gave up three free agent years in a contract extension with the Los Angeles Angels. It was a deal that turned to be a steal for the team and a surely regrettable one for Trout. Not only did he miss out on more money, but he could’ve been playing for a better team and maybe even won a World Series. So, what if Mike Trout never signed that extension? I decided to look at an alternate timeline up until today, that would take place if he didn’t sign that notorious extension.

March 2014-November 2016: The Los Angeles Angels try to extend Trout a few times, but he continues to refuse extensions going into the 2017 season, Trout’s last under contract with the team. They still haven’t made the playoffs since the 2014 season and there’s now serious concern that they could lose Trout and receive nothing but a draft pick in return. They also don’t want the fan backlash from trading him, so they decide to go all-in for 2017. I don’t think that free agency goes much differently that off-season as they were all-in already and it’s hard for me to see any of the top free agents signing with them instead of the teams that they actually signed with.

July 31, 2017: The Los Angeles Angels have a record of 51 wins and 55 losses. More importantly however, they’re 18.5 games out of first place in the division. They’re clearly not going to the playoffs. The question is whether they will trade Trout now. Every contending team is interested, but no one is really willing to pay the price. The New York Yankees are more focused on pitching and first base help; Boston doesn’t have the prospects; Cleveland can’t afford his salary and aren’t willing to sell the farm that they so badly need as a small market team; Kansas City won’t gut their farm for Cleveland’s reason; Minnesota aren’t even sure they’re truly contenders; Houston are more focused on their questionable rotation and have a great lineup as it is; Washington have interest but are wary about hurting their farm (though make the biggest push); the Chicago Cubs don’t have the prospects; Milwaukee and St. Louis won’t gut their farm when they’re barely contending and trading Trout to the Los Angeles Dodgers, (who at that point are the favorites to win the World Series) would have to take a return they wouldn’t even consider paying. As a result of all of this, Trout stays in Anaheim as the trade deadline passes. They put him through waivers in August, but a trade during the waiver trade deadline is impossible.

November 2017: Mike Trout becomes a free agent and declines a qualifying offer.

January 2018: The most anticipated tenure in free agency of all-time finally ends as Trout picks his team. By this point the teams with a serious chance of signing him are the: New York Yankees, Los Angeles Dodgers, Boston Red Sox, San Francisco Giants, Los Angeles Angels, St. Louis Cardinals, Chicago Cubs, Chicago White Sox and the Philadelphia Phillies.

The race to sign Trout eventually winds down to just two main favorites: New York and Philadelphia. St. Louis and the Chicago White Sox are unwilling to bid at the top of the market, then Trout turns down Anaheim due to giving up on them building a winner around him and is too respectful to his former team to sign with their biggest rivals (who are themselves hesitant to give out a monster contract). He isn’t interested to go to San Francisco with their weak farm, bad management and status as a team that’s refusing a needed rebuild. He also turns down Boston due to their weak farm, too many upcoming key free agents and two straight ALDS exits. He doesn’t seem too interested in the Chicago Cubs and they refuse to go as high as New York and Boston anyway.

Ultimately, it comes down to choosing between his favorite team growing up (and the closest team to his current hometown of Bridgeton, NJ), that has money and promises to build a winner or a team that was a win away from a pennant with a history of typically annual contention. It comes down to him possibly not wanting to come off as a villain in Philadelphia by going to New York and Philadelphia going higher than imaginable and thus he ends up signing with them. 10 years/$500 million with opt-outs.

Unfortunately, it turned into a boring prediction for me. I don’t see Philadelphia going to the playoffs in 2018 anyway and the rest of the offseason goes the way it actually did, so Boston still win the World Series. Boston fans mock Trout for not choosing Boston and are happy to show that they won without him. The Angels are terrible but hesitate to tear down the team for another year.

What if he chooses the Bronx Bombers? Well for one thing Twitter explodes and Trout becomes a villain to fans of all of the other teams. The team meanwhile trades Aaron Hicks to San Francisco for prospects to save money and since he wouldn’t be re-signed the following year upon hitting free agency anyway. In the meantime, Miami trades Giancarlo Stanton to the Los Angeles Dodgers for their bad expiring contracts.

October 2018: Nothing changes besides Trout’s team if he signs with Philadelphia the previous year, if he signs with New York however… the New York Yankees rally to win game 4 of the ALDS and force a game 5 in Boston. This could go either way, but suppose Trout has a big game and wins the series with a crucial RBI double? New York then goes on to beat Houston in the ALCS and Los Angeles with Stanton in the World Series. Stanton is awful during that series and sportswriters bring up the rumor that he was heading to New York if Trout would’ve signed with Philadelphia.

January 2019: Bryce Harper and Manny Machado choose their new teams in free agency. If Trout signed with Philadelphia, then the New York Yankees sign Machado and as far as Harper goes, he signs with whomever he signs with in real life, just not with New York or the Los Angeles Dodgers. If Trout signed with New York, then Philadelphia signs Machado and Harper signs with whichever team he will with in real life, other than New York.

In conclusion, I think that Trout should’ve refused to sign any extension and hit free agency after the 2017 season. Had he done so, he would’ve gained more money and possibly won a World Series. Even if he wanted to stay with the Los Angeles Angels, he could’ve done so for more money had he re-signed with them as a free agent instead of signing that notorious extension.

What do you think? What would happen if Trout was a free agent last off-season?