I reckon that Zenit St. Petersburg is one of the worst draws Liverpool could receive.
Not only is it another long, debilitating trip to Russia (I hear Russia is lovely in February!), but Zenit are an incredibly talented side. Or, at least, they've got an awful lot of incredibly talented players: Hulk, Danny, and Kerhakov in attack; Witsel, Shirokov, Denisov in midfield. Bruno Alves and Lombaerts are both outstanding center-backs, Malafeev a talented keeper, and Anyukov is Russia's starting right back.
Managed by Luciano Spalleti, formerly of Roma, Zenit play a 4-3-3 system – very similar to the 4-1-2-3 Rodgers has used since Lucas' return – but a system which thrives on the counter-attack. You know, the style of play that Liverpool's all-too-prone to conceding against.
There are a couple of positives. Zenit, like Liverpool, are often worse than the sum of their parts suggest they should be. They've only lost three league matches – against Rubin Kazan and Terek Gronzy at home and Dynamo Moscow away – but have drawn five (joint-most in the division) and were outgunned in its Champions League group, losing to Anderlecht and Malaga away, and AC Milan at home; they were the only side that Anderlecht beat in that group. A last day win at already-qualified AC Milan is the only reason the group looks close after the fact, but Zenit had little chance of progression after losing its first two fixtures.
Both Hulk and Witsel have struggled to settle, each costing €40m this summer, leading to this wonderful, tolerant, certainly-not-racist letter from a Zenit fans' group currently making the rounds. Hulk's decision-making often sucks, too frequently too greedy and selfish, but on his day, he's lightening quick, direct, and can score from anywhere – again, just the type of player who often punishes Liverpool. Danny's slow return to form and fitness following an eight-month layoff from February through September due to a cruciate injury should improve Zenit tremendously; he was the star player against Spartak and AC Milan before picking up a red card for dissent in the match against Anzhi last week.
The St. Petersburg club is currently third in the Russian League, three points behind Anzhi, a side Liverpool beat fairly easily – despite the 1-0 scoreline – when using a strong line-up at Anfield, and narrowly lost to in Russia with a vastly weaker squad. Zenit has faced Anzhi twice, home and away, and drew 1-1 both times. The transitive property suggests that Liverpool have an excellent chance to advance to the next round, but then again, the transitive property rarely if ever works in football.
Finally, Zenit will face Liverpool having spent two months without playing competitive football. That 1-1 draw against Anzhi on December 10 was the final fixture before the Russian Premier League's winter break; the league won't resume until early March. This happened the last time Liverpool were in the Europa League, facing Sparta Prague in the round of 16, who clearly felt the effects of the Czech League's three-month break. Of course, Liverpool were also poor, needing a late late late second leg goal from Kuyt to progress 1-0 on aggregate, but of course they did because Liverpool.
If Liverpool advance, they'll face the winner of the Basel-Dnipro tie, with the latter side both seeded and favored. We can complain about the next bridge after getting over the first, but the last thing Liverpool will need after a trip to Russia is one to the Ukraine.